Journal of Fluorescence (2023) 33:1273–1303

https://doi.org/10.1007/s10895-023-03153-y

REVIEW

Naphthalene and its Derivatives: Efficient Fluorescence Probes

for Detecting and Imaging Purposes
Ruqaya Irshad1 · Sadia Asim2 · Asim Mansha3 · Yusra Arooj1

Received: 24 October 2022 / Accepted: 19 January 2023 / Published online: 3 February 2023
© The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature 2023

Abstract
Naphthalene, white crystalline solid having polycyclic aromatic hydrocarbon with characteristic mothball order is naturally
present in crucial oils of various plants. Naphthalene derivatives are extensive drug resources and are use as wetting agents,
surfactants and as insecticides. These derivatives exhibit unique photo physical and chemical properties. These character-
istics make them the most studied group of organic compounds. Naphthalene dyes have rigid plane and large π-electron
conjugation. Therefor they have high quantum yield and excellent photostability. Naphthalene based fluorescence probes
due to hydrophobic nature exhibit excellent sensing and selectivity properties towards anions and cations and also used as
a part of target biomolecules. In conjugated probe system, introducing naphthalene moiety caused improvement in photo-
stability. Therefore among various conjugated framework, naphthalene derivatives are considered excellent candidate for
the construction of organic electronic appliances. These derivatives are useful for a variety of applications owing to their
strong fluorescence, electroactivity and photostability. This article is based upon investigation of photophysical properties
of naphthalene derivatives and fluorescence detecting probe of naphthalene. For photophysical properties the techniques
under investigation are UV visible spectroscopy and fluorescence spectroscopy. Concentration dependent spectra and solva-
tochromic shifts on UV visible spectra are also part of discussion.

Keywords Naphthalene · Naphthalene derivatives · Absorption spectra · Fluorescence probe · Quantum yield

Introduction basically known as organic fluorophore emits fluorescence

when stimulated by light. These organic fluorophore have
Fluorescence microscopy is an important technique used in attracted much attention of researchers. Because in the field
several productions and research fields. Fluorescent com- of both industry and basic science organic fluorophores are
pounds have wide scope as photoelectric material, multi- widely used due to increased selectivity and sensitivity [1].
purpose dyes and chemical biology. An organic molecule Organic fluorophores that build with naphthalene core are
called dyes, fluorescent probe and luminescence sensors
* Sadia Asim [2]. Naphthalene is considered a suitable fluorescent che-
[email protected] mosensor because it has high values of fluorescent lifetime
Ruqaya Irshad and prominant fluorescent quantum yield and also it acts
[email protected] as donor as well as acceptor [3, 4]. A conjugated pi-system
Asim Mansha chemically modified with both an electron-donating and an
[email protected] electron-withdrawing group is a structural element that is
Yusra Arooj shared by most fluorophores. For a lot of the pi-system is
[email protected] composed of naphthalene moiety in fluorophores. Typically
chromophore synthesis starts with commercially available
1
Department of Physics, Government College Women naphthalene [5]. Naphthalene moiety easily combine with
University, Faisalabad, Pakistan
hydrophilic tail which increase its solubility in water. Hence
2
Department of Chemistry, Government College Women it becomes suitable for observation of AL+3 in living cells
University, Faisalabad, Pakistan
[3]. Introducing naphthalene moiety in laser dyes, the ampli-
3
Department of Chemistry, Government College University, fied spontaneous emission (ASE) wavelength transfers to
Faisalabad, Pakistan

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the longer wavelength and optical properties of laser dyes

enhances [6]. Naphthalene dyes have superb rigid plane
and large π-electron conjugation. Therefore they have high
quantum yield and excellent photostability. Furthermore,
by adding substituent group at suitable positions, desired
spectroscopic and photophysical properties can be achieved.
Due to their extremely sensitive absorption and emission
characteristics, they have recently been reported for envi-
ronmentally responsive probes as well as biological sensing
and imaging probes [7].

Toxicity of Naphthalene

Naphthalene (a polycyclic aromatic hydrocarbon) [8–11] is

extensively used chemical in industry as well as household
[12]. Sufficient amount of naphthalene is present in air and
it is a respiratory toxicant and a possible human carcinogen
[13]. Naphthalene can be exposed through traffic exhaust,
moth repellents [14], industrial sources airborne, cigarettes
smoke [15], open burning, off-gassing from products that
contains naphthalene [16] and combustion of fossil fuel [17].
Naphthalene exposure can involve disorder in several organ
systems, which include the liver, blood cells, gastrointesti-
Fig. 1  Structure of Naphthalene Diimide (NDI) [27]
nal tract, respiratory system and nervous system. Different
diseases like hemolysis and hemoglobinuria, cataracts [18],
increase in incidence and severity in olfactory epithelial 2). They have specific redox activity. For synthesizing dif-
metaplasia [19], in nose cause hyperplasia of respiratory epi- ferent NDI derivatives, 1,4,5,8-Naphthalenetetracarboxylic
thelium and chronic inflammation [20], laryngeal tumours, dianhydride (NDA) acts as main precursor. NDIs are used in
haemolytic anaemia [21], kidney failure [22], methemo- many organic electronic applications because of bathochro-
globinemia [23], confusion, vomiting, headache [24] and mic changes in the visible region and improved solubility in
lung toxicity by inhaled naphthalene [25] has been reported organic solvents [31], high electron affinity [32], outstand-
due to naphthalene exposure. Naphthalene is also an aquatic ing thermal and oxidative stability and fine charge carrier
environmental pollutant. It releases to water from different mobility [33].
processes like distillation process, petroleum spillage, coal In suitable conditions, different nucleophiles can be sub-
tar production and oil spills. Aquatic animal inhales naph- stituted in the aromatic ring of NDI. Resulting derivatives
thalene by oral route, breathing and absorption through their are called core-substituted Naphthalene-Diimides(cNDI).
skin. It induce physiological, behavioral and biochemical These derivatives have remarkably different photophysical
changes in these animal [26]. and redox properties than their parent NDI [33]. For supra-
molecular assembly and functional materials, Naphthalene
Naphthalene Derivatives and Their Activities Diimides and its substituted derivatives are extremely prom-
ising candidates [28]. All NDIs are sensitive to temperature
Naphthalene and its derivatives are extensively encountered and variation from moderate-to-high sensitivity and electri-
in natural products, pharmaceuticals and also in materials cal conductivity is observed with the increase of tempera-
science [28]. Derivatives of naphthalene are also useful drug ture. This capability make them a potential candidate to be
resources. Nafacillin, naftifine, tolnaftate and terbinafine are used as temperature sensors [34].
some common naphthalene containing drugs. In the control Derivatives of naphthalene are used in organic elec-
of microbial infection these drugs play an important role. tronic applications to fabricate optimistic materials [36].
Naturally occurring naphthalene products possessed a num- The 6-acetly-2(dimethylamino) naphthalene and 4-amino-
ber of biological possessions including antioxidant, antipro- 1,8-naphthalimide derivatives are extensively used as fluo-
tozoal, antimicrobial, anti-inflammatory and cytotoxic [29]. rescence prob platforms. Interchanging the electron push/
Naphthalene is insoluble in water but it dissolves in binary pull character, desirable photophysical properties could be
solvent (water–ethanol) [30]. Naphthalene-Diimides(NDI) attainable [37]. Naphthalene sulfonates (NSs) are highly
are well known neutral and planer compounds (Figs. 1 and toxic and soluble in water. They are mainly used as wetting

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Fig. 2  a Structure of some core-

substituted naphthalene diimide
[35]. b Chemical formula and
structure of some naphthalene
sulphonates [40]

and tanning agents (Fig. 2b) [37], optical brightener in paper due to excimer formation. Literature shows that UV–visible
industry [38], solubilizing and dispersing in formation of spectra of PAHs containing 2 or 3 rings like naphthalene
different industrial products. These products include ion exhibits powerful absorption in the ultraviolet absorption
exchange resins, optical brighteners, pharmaceuticals,, pes- analogues to 𝜋 − 𝜋 ∗ transition and also shows appreciable
ticides, plasticizers and azo dyes [39]. fine structure accompanied particular absorption bands of
Compounds derived from 1,8-naphthalic anhydride conjugated aromatic bonds [30]. In concentrated solutions,
and 1,8-naphthalimide shows fluorescence properties and naphthalene exhibits high relative fluorescence quantum
broad stokes shift values. These compounds can also be yield. Fluorescence excimers of naphthalene forms due
used for newly of fluorescent bioactive compounds and to reaction of excited and unexcited monomers. A sharp
in bio-imaging investigations [2]. 1,8-Naphthalimide- excimer fluorescence band revealed in the fluorescence
containing compounds have found use as liquid–crystal spectrum of naphthalene in solution which is highly con-
displays, optical brighteners, fluorescent dyes for wool centration and temperature dependent [54]. Both static and
fibers [41], photoinduced electron transfer (PET) fluo- dynamic excimers of Naphthalene and its derivatives have
rescence sensor [42] and fluorescent molecular probes been reported. Dynamic excimers formation were observed
[2, 43]. Naphthalene derivatives show powerful excimer in Naphthalene Polyaminic derivatives in ethanol and water
emission in concentrated solutions because of neighbor- solvents. The dynamic excimers were studied by steady state
ing molecule’s attraction. They are extremely fascinating and time resolved fluorescence data and when the fraction
fluorescent compounds due to the reason that excimers of of ground state excitable dimers approaches 1 then dynamic
these derivatives are susceptible to temperature and local formation of excimers was lost beneath the large contribu-
environmental properties. Subsequently these situations tion of the static formation. This was evident from the loss
can be used in the formation of fluorescence molecular of linearity in Arrhenius plot at low temperature [55]. Simi-
thermometers and metal ions detectors [44]. Fluorescent larly Naphthalene appended diformyl-p-cresol derivatives
probes based on excimer can be employed extensively in reflects concentration dependent dynamic to static conver-
a variety of scientific and technological sectors. They can sion of excimers in presence of ­Sn2+. Formation of dynamic
be utilised, among other things, as selective fluorescence excimers were observed in the presence of S ­ n2+ up to 2.5
sensors for the detection of metal ions [45], fluorescent equivalents and upon further addition of ­Sn2+ conversion
probes for the detection of amino acids [46], DNA [47], into static form was observed [56].
Biothiols [48], enzymes [49] and other biomarkers in bio-
sensing processes, as well as for the imaging of living cells Effect of Solvent Polarity on Emission
and bacteria [50] (Fig. 3) Organic electronics is another and Absorption Spectra of Naphthalene and Three
field in which excimer-forming substances are employed Bridged Disilanes
to create novel materials for OLED applications [51, 52].
In polysilanes sigma conjugation is present at catenated
silicon atom. This sigma conjugation enhances the photo-
Photophysical Properties of physical properties of polysilanes. Change is observed in
Naphthalene Derivatives absorption of polysilanes changed due to change side group
at silicon atom. Naphthalene attached to the silicon atom
Naphthalene and its derivatives are most studied group cause red shift in UV absorption spectrum due to increase in
of organic compounds because they have attractive pho- 𝜎 − 𝜋 mixing. As 𝜎 − 𝜋 mixing increases the semiconduct-
tophysical properties. These photophysical properties are ing properties of material also increases. Three derivatives

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Fig. 3  Fluorescent and Confocal microscopy image of distrylnaphthalene core derivatives. Results shows that these derivatives could be safely
used in the human and animal studies [53]

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conjugation of birdged system. By varying solvent polarity,

naphthalene and 1b, 3b compounds show little tendency of
absorption. The emission spectra for same solvent polarity
displays maximum wavelength at 305 nm for three deriva-
tives but in case of naphthalene it was 286 nm. In acetonitrile
and THF, vibronic fine structure was recorded for bridged
silanes with maxima at 335 and 345 nm. This spectral pro-
file showed fine resemblance to naphthalene. For non-polar
solvents, the spectral behaviour is completely changed. In
non-polar solvent a broad emission band was observed at
wavelength > 400 nm (Fig. 5). This additional broad band
indicated the formation of excimers. This additional broad
Fig. 4.  1a, 2a and 3a (Substituted disilyl naphthalene precursors) and band was not observed in the case of naphthalene.An exci-
1b, 2b, and 3b (naphthalene bridged disilanes) [34] mer (originally short for excited-dimer) is a short-lived
dimeric or heterodimeric molecule produced from two iden-
tical species, one at excited state and other at ground state
naming 1b, 2b and 3b were prepared by Kumar et.al. out of [44, 57]. Excimer formation was observed at higher concen-
them two are structural isomer of each other (Fig. 4). These tration and upon dilution decrease was observed in emission
precursors were then subjected to intermolecular dehydro- intensity of excimer reflecting decrease in concentration of
coupling using toluene to form naphthalene birdged disilane. excimer. Therefor the broad band due to excimer formation
Naphthalene was chosen as parent compound for compar- at wavelength > 400 would decrease in dilute cyclohexane
ison of absorption and emission spectra. These spectra were for compounds 1b, 2b and 3b (Fig. 6). Possibilities to use
obtained in different polarity of organic solvent. The birdged this substance in applications like light emitting devices or
disilanes showed increased red shift in absorption spectra as a photocurrent generator in solar cells are provided by the
with respect to naphthalene. Thus, indicating extension in photoluminescence discovered for 2b [34].

Fig. 5  Absorption and emission spectrum of naphthalene, 1b, 2b, and 3b [34]

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Fig. 6  Concentration dependent emission spectrum of naphthalene and three bridged disilanes [34]

Regioisomerism Effect on the Physical Nature UV–visible Absorption and Fluorescence Spectra
of Naphthalene Alkylated Liquids of Alkylated Naphthalene Liquids (1‑regioisomer
and 2‑regioisomer)
The viscous loss modulus and storage elastic modulus were
measured at a range of applied angular frequencies. The Nanoscale structural information could be gathered by optical
storage elastic modulus was lower than viscous loss modu- spectroscopy in solvent-free liquid state and dilute-solution.
lus. This behaviour indicates an intrinsic liquid behaviour. For dilute solution of 1 in n-hexane peak maximum at 294 nm
Decrease was observed in complex viscosities in compari- was observed (Fig. 8a).
son to previous reports. Small values were due to small Peaks in Fig. 8 indicates structure less absorption fea-
sized molecules. It was observed that with decrease in size ture. Absorption spectrum of 2 exhibits more vibronic
of molecule (long chain alkyls were used) increase was features which was not seen in other naphthalene regioi-
observed in the value of complex viscosity. Two large halos somers. It was concluded that both regioisomers had
were observed in graph for all samples (1–6) Fig. 7a, b. constitutionally different electronic structure. Both
Large halos indicated the amorphous nature for 1-alkoxy regioisomers showed monomeric fluorescence feature
regioisomer and 2-alkoxy analogues regioisomer. The halo but fluorescence quantum yield was less for 1 then 2 in
that was observed at greater q value represented molten solution. In solvent-free liquid state, a red shift of few
state of alkyl chain. The average naphthalene-naphthalene nanometers in absorption spectra was observed for both
distance was represented by diffused halo at low q value. regioisomers. Monomer mixed with excimer-liked emis-
Presence of naphthalene units investigated by breadth of sion was observed from fluorescence spectrum of 1. But
halo [58]. for compound 2, monomer-enriched emission with very

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Fig. 7  a Structures for

regioismomeric liquid
naphthalenes (1–6). Odd series
express the 1- regioisomers
whereas, even series represents
the 2- regioisomers [58]. b
SWAXS profiles for regioisomers
1 and 2 [58]

small excimer feature was observed. In solvent-free liquid observed for derivatives with long substituted alkyl chains.
state greater values of fluorescence quantum yield were It was concluded that probability of self-quenching could
observed in comparison to n-hexane. Higher values were be reduced by long chain substituent [58].

Fig. 8  Normalized UV–visible absorption spectrum and fluorescence spectrum [58]

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Fig. 9  Schematic synthesis of

naphthalene 1–8 derivatives [2]

Photophysical Properties of 1,8‑naphthalic anhydride 1, a broad emission band was observed over
Anhydride and 1,8‑naphthalimide Derivatives 400 nm. Similar spectral pattern was displayed by naphthal-
with Different Solvent Polarities imide derivatives 5 to7. From polar to non-polar solvents,
a bathochromic shift was observed in absorption band for
The UV–Visible absorption spectrum of compounds derived derivatives 2–4 and 5–7. For derivatives 2–4 and 5–7 high
from naphthalene-1,8-dicarboxylic acid were studied at dif- value of red shift was observed in dichloroethane. But com-
ferent solvent polarities (Fig. 9). The UV–Visible absorption pounds 1 and 8 showed lower red shift which indicates weak
spectrum was bit similar for naphthalimide derivatives and interaction between solute and solvent [2].
naphthalic anhydride derivatives. Main absorption band was
detected at 390–430 nm (Fig. 10). Absorption peaks at longer The Photophysical Properties and DFT Calculations
wavelength were due to π-π* transition or first excited singlet of Core‑substituted Naphthalene Diimide
in the absence of vibrational structure. A hypochromic shift with Fullerene, NDI −C60 (S4) and C_60‑NDI‑C_60 (S5)
of absorption band was observed for compounds 4 and 7 as
compared to compounds 2, 3 and 5, 6 due to the existence The UV–vis absorption spectra in CHCl3 and in pristine thin
of methyl piperazine moiety. The hypochromic shift is dis- film of dyad S4 and triad S5 are shown in Fig. 11. While S5
placement of signal or spectral band from longer to shorter displayed two absorption peaks at 380 nm and a broad inten-
wavelength. The compounds 1 and 8 showed different spec- sity peak at 490 nm, S4 displayed three absorption maxima
tral behaviour. A wide absorption band having vibrational at 360 nm, 380 nm, and 470 nm (broad peak) in CHCl3. The
structure was observed with a maximum at 340 nm. In case 400–600 nm range of absorption peaks is occupied by fullero-
of N-substituted derivatives by 4-chloro-1,8-naphthalic pyrrolidine moieties. S4 has less pronounced peaks at 360 nm

Fig. 10  UV–visible absorption spectra of a the naphthalic anhydride derivatives (1,2,3,and 4) b the naphthalimide derivatives in DMF [2]

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Fig. 11  The UV–vis absorption spectra of S4 and S5 in (a) ­CHCl3 and (b) as a pristine film [59]

and 380 nm together with a broad peak at about 490 nm in its molecular orbital) disperse over the fullerene moiety and
purest film form. When contrasted to its solution absorption LUMO + 1 was localized over NDI subunit. Same results
peak, the pristine film of S5 had a broad absorption maximum were observed for S5. Both HOMO and LUMO were local-
at 550 nm with a red-shift of 60 nm. The optical band gap ized for fullerene unit and LUMO + 1 was acquired by the
values for S4 and S5 were calculated using the absorption NDI unit. For both molecules HOMO and LUMO + 1 distri-
onset values of their thin film spectra, which were 653 nm and bution were totally separated. Thus, charge separation was
752 nm, respectively. The intermolecular 𝜋-𝜋 stacking interac- greater for excited state as compared to ground state. The
tions between NDI cores are responsible for the bathochromic HOMO energy levels for S4 were -5.74 eV and for S5 were
shifted absorption maxima of S4 and S5 in their thin film -5.65 eV. The HOMO energy level was greater for S5 than
forms relative to their solution spectra (Fig. 11). S4. But the LUMO energy level -4.0 eV was same for both
The DFT calculations were carried out for S4 and S5. S4 and S5. The value of band gap was 1.70 eV for S4 and
It was observed that for S4 the HOMO (the highest occu- for S5 was 1.61 eV which were taken by the density state
pied molecular orbital) and the LUMO (lowest unoccupied spectra (DOS) (Fig. 12) [59].

Fig. 12  Frontier molecular orbitals of S4(a) and S5(b) [59]

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Effect of Extended Conjugation on Naphthalene When treated in different solvents, insignificant varia-
ring in 1,8‑naphthalimides Derivatives in tion in absorption spectra in the range of 367 nm-378 nm
Different Solvents and significant change of emission spectra form 441nmm
to 544 nm was observed for compound 1. In Pyridine,
1,8-naphthalimides and its derivatives shows extraordinary DMSO and MeOH long emission spectra were examined
photophysical properties because of unique structure. Large as a result of solvation effect as compared to MeCN and
stock-shift, strong luminescence and high photo stability are THF. High quantum yield was observed for DMSO but
their important features that used to design fluorescence sen- pyridine and MeOH showed relatively low quantum yield.
sors. Because NIs are excellent imaging agents and fluorescent The compound 2, having phenyl group as substituent on
dyes. Substitution on naphthalene ring, especially at 3 and 4 naphthalene ring, exhibited solvent polarity dependent
position, changes the optical properties of NIs. The spectral emission spectra but absorption spectra did not depend
properties of NIs highly affected by electronic properties of on solvents. Increase of emission wavelength in case
substituted group because their photophysical properties are of MeCN observed from 452 to 500 nm and in DMSO
drastically responsive to the substituent on naphthalene ring at decrease in emission wavelength from 544 nm-521 nm
position 4. A strong fluorescence was observed when the sub- indicated the dependance of emission wavelength on sol-
stituent at position 4 was strong electron donating group, due to vent medium. The compound 3, which was designed by
charge transfer. But electron withdrawing group caused weak substitution of biphenyl group, exhibited red-shifted emis-
fluorescence. The fluorescence spectra of NIs were also influ- sion spectra in acetone, THF and MeCN but in MeOH
enced by solvent polarity by generating large stokes-shift. 5 NIs emission decreased. The compound 4 having naphthalene
derivatives using Suzuki coupling reaction were prepared by as substituent showed similar results as compared to com-
substituting different groups on 4-position of naphthalene ring pound 2. However the compound 5 with pyridinyl moiety
of 1–8 naphthalimide (1–5) (Fig. 13). The absorption and emis- at position 4 showed longer wavelength emission in com-
sion spectra of derivatives (1–5) were measured in different parison with compound 2. These observation of absorption
solvents. A compound without conjugation on naphthalene ring and emission spectra confirmed that expended conjugation
(1) was chosen as reference. Typically emission of NIs as fluo- caused miner increased in absorption and appreciably long
rescence probe was represented in range of 350 nm-500 nm. emission (Fig. 14) [60].

Fig. 13  The artificial preparation method for 1–5 [60]

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Fig. 14  Absorption and emission spectra of 1,8-naphthalimides derivation (1–5) having extended conjugation on naphthalene ring in different
solvents [60]

Effect of Solvent Polarity on 1,8‑diarylnaphthalene totally independent of organic solvent polarity. Compound
(1a‑h) and 1,8‑diarylethynylnaphthalene 1 g having dimethylamino, a strong electron-donating group
(2a‑g) Derivatives and compound 2 g with cyano, electron-withdrawing group
showed same absorption spectra in different solvents. Com-
1,8-diarylnaphthalene and 1,8-diarylethynylnaphthalene are pletely different behaviour was observed for emission spectra
U-type naphthalene based fluorophores (Fig. 15). The solva- of all these compounds. Compounds 1a, 1b, 1 h, 2a and 2b
tochromism of different derivatives of 1,8-diarylnaphthalene were unaffected by varying solvent polarity. But red-shifted
(1a-h) and 1,8-diarylethynylnaphthalene (2a-g) was checked by spectra were observed for 1c, 1d, 2c and 2d with the increase
changing the polarity of solvents. The absorption spectrum of in solvent polarity.
1,8-diarylnaphthalene (1a-h) and 1,8-diarylethynylnaphthalene Unlike above, emission spectra of compounds 1e, 1f,1 g,
(2a-g) recorded near 300 nm and 345 nm respectively were 2e, 2f and 2 g were highly affected by solvent polarity.

Fig. 15  Synthesis of naphthalene-

based, U-type fluorophores [61]

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The solvent polarity dependence was well explained by and acceptor, it was inferred that they may also be utilised as
standard dipole model. According to this model, electronic solvent polarity sensors or pH sensors [61].
transition takes place when a fluorophore excited from
S◦ to S1 state and S◦ possessed smaller dipole moment than Effect of Silyl Substitution on UV Visible Absorption
S1 state. For derivatives 1c, 1d, 2c and 2d, polar solvent and Fluorescence Emission Spectra of
arranged around S1 state and consequently energy level Naphthalene Derivatives
of S1 decreases. This effect was increased by increasing
solvent polarity. Lower quantum yield and large Stokes’ Introduction of silyl group on aromatic hydrocarbon (naph-
shift were exhibited by 1,8-diarylethalene as compared to thalene, anthracene), intensify the fluorescence intensi-
1,8-diarylethynalnaphthalene. Quantum efficiencies were ties. When naphthalene chromophore was substituted with
examined taking 9,10- diphenyl anthracene as reference. The silyl group at position 1 and 1,4 then bathochromic shift
series of 1,8-diarylethynylnaphthalenes 2a–g showed much was observed for absorption maxima. Peaks of absorption
higher quantum yield then those of 1,8-diarylnaphthalenes spectra were shifted to longer wavelength and fluorescence
1a–h series in cyclohexene. That is due to better conjugation intensities also increased. For derivatives 2–6, absorp-
of naphthalene and aryl group (Fig. 16). Since the solvent tion maxima shifted to longer wavelength (8-9 nm) and
polarity and environmental acidity had a significant impact molecular absorption coefficient also increased as com-
on the emission performance of these compounds with donor pared to naphthalene(1). Identical results were observed for

Fig. 16  The absorption and emission spectra of derivatives of 1,8-diarylnaphthalene (1a-h) and 1,8-diarylethynylnaphthalene (2a-g) in
cyclohexene [61]

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emission spectrum. Bathochromic shift of emission spectra and ICT peaks at about 576 nm(0,1), 617 nm(0,0) transition.
and also increase in fluorescence intensities was observed. In emission spectra the main peck was observed at 644 nm
When substitution was attached on silicon of silyl group, with small shoulder peak at 700 nm. As compared to Naph-
the absorption and emission spectra was slightly affected PDPP, the absorption bands of 𝜋 − 𝜋 ∗ and ICT transition of
and is shown in Fig. 13. 4-cyano, 5-cyano and 4-methoxy Naph-TDPP shifted to longer wavelength due to existence
groups also effects shift in absorption maxima, shift it to of electron rich thiophene rings.
longer wavelength and cause a bit increase in molar absorp- Similarly and emission spectra of Naph-PDPP and Naph-
tion coefficient. HOMO and LUMO energies of naphthalene TDPP were also examined in thin film which was coated
are also increased by introduction of silyl group due to its on quartz plate. In solid state the molecules were closely
electron donating capability (Fig. 17) [62]. packed and consequently increase in their intermolecular
interactions were observed. This enhancement of interac-
Absorption and Emission Spectra of Naph‑PDPP tion caused red-shift of absorption and emission peaks as
and Naph‑TDPP in Chloroform and in Thin Film compared to solution. The red-shifted absorption peak was
Coated on Quartz Plate observed at 60 nm and red shifted broad emission peak at
32-50 nm. Through de-convolution calculation Naph-PDPP
Naph-PDPP and Naph-TDPP with phenyl and thiophene exhibited three emission peaks at 675 nm, 630 nm and
formed donor–acceptor-donor (D-A-D) structure in which 595 nm, respectively. At the same time, Naph-TDPP thin
rigid conjugated naphthalene acts like a donor and planer films showed stokes shift of ~37 nm along with the emis-
DPP like an acceptor. J-type aggregation was observed due sion peak at 744 nm and 695 nm and a new wide emission
to strong intermolecular 𝜋 − 𝜋 stacking in Naph-PDPP and peak appearing at 812 nm. The overall attenuation of emis-
Naph-TDPP. The absorption and emission spectra of these sion was promising and indicates the existence of the excited
compounds were examined in chloroform solvent. The state competing process (Fig. 18) [63].
absorption spectra consist of two well defined peaks. First
peak was associated with the conjugated backbone resulting Solvent Polarity and pH Dependent UV–visible
from 𝜋 − 𝜋 ∗ transition and second peak for DPP chromo- Absorption and Emission Spectra of Halochromic
phore due to intermolecular charge transfer. For Naph-PDPP 2,6‑Distyrylnaphthalene Chromophore
first peak was located at 348 nm and second at 496 nm.
However the emission spectra showed some distinct behav- A donor-pi-acceptor (D-π-A) conjugated system was synthe-
iour. The main emission peak exhibited at 563 nm having a sized by Panahi et al. A donor- π-acceptor conjugated system
wider shoulder emission peak low-energy at 610 nm. Similar based on 2,6-distyrylnaphthalene chromophore (ASDSN)
result of absorption spectra were observed for Naph-TDPP, having electron donating group amino, electron withdrawing
where first peak observed at 412 nm due to 𝜋 − 𝜋 ∗ transition group sulfonyl and π as conjugated moiety (Fig. 19).

Fig. 17  The absorption and emission spectra of 1- and 1,4-Silyl-Substituted Naphthalene Derivatives [62]

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1286 Journal of Fluorescence (2023) 33:1273–1303

Fig. 18  Absorption spectra of Naph-PDPP and Naph-TDPP in chloroform solution(left) and in thin film(right) [63]

Effects of solvent polarity was obtained by UV–visible 7 to 4, there was no significant change in absorption and
absorption and fluorescence emission spectroscopy, on emission profile of ASDSN (Fig. 20). But remarkable blue
the chromophore from lower to higher polarity solvents. shift was observed in absorption and emission spectra of
The absorption spectra of ASDSN chromophore exhibited ASDSN when pH decreased from 4 to 1. Besides that, col-
structureless broad band at 400 nm, indicating a push–pull orimetric effect was also observed as the solution having
character of amino (donor group) and sulfonyl (acceptor ASDSN chromophore changed from yellow to colorless
group) due to ICT transition. Solvent polarity variation with alteration in fluorescence from yellow to blue. The
caused a small change in absorption band of chromophore blue shift for both absorption and emission spectra were
which is attributed to low ground state dipole moment of found at 121 nm (for absorption) and 132 nm (for emis-
ASDSN. The chromophore displayed fluorescence emis- sion) with varying pH from 7 to 1 (Fig. 21). These results
sion only in xylene solvent with maximum emission band suggested protonation process in chromophore by adding
at 557 nm (Fig. 20b) and exceptional 0.49 fluorescence TFA, because it decreased the ICT character of ASDSN.
quantum yield. In polar solvents fluorescence quenching White light emission was observed at pH 3 which indi-
was observed which was strong in case of highly polar cated that protonated and neutral chromophore at specific
solvents due to non-radiative relaxation mechanism. Polar pH exist in the solution and caused emission of white light.
solvents tend to stabilize the excited state by decreasing The 13% white light quantum yield (F) that the ASDSN
the energy between the ground and excited state. chromophore displayed was sufficient for making white
To find out effect of pH on ASDSN chromophore, the light emitting devices [64].
absorption and emission spectra were conducted on mix-
ture of xylene and different amounts of trifluoroacetic Effect of Solvents on Absorption and Emission
acid. It was observed that when the pH was decreased from Spectrum of Pyrene‑naphthalene Sulphonyl Conjugate

A new synthesized pyrene-naphthalene sulphonyl con-

jugated probe PSN consist of sulphonyl unit as electron
withdrawing group and naphthalene and pyrene unit as
electron donating groups (Fig. 22).
The compound is highly soluble in organic solvents and
insoluble in ethanol, methanol and water. Photophysical
properties of the compound PSN was due to the polariza-
tion mechanism of chromophoric unit alkene, naphthalene
and pyrene. The absorption spectra of compound PSN dis-
Fig. 19  donor- π-acceptor conjugated system based on 2,6- played two types of transition dependent bands due to conju-
distyrylnaphthalene chromophore (ASDSN) [64] gation of electron donating and electron withdrawing groups.

13
Journal of Fluorescence (2023) 33:1273–1303 1287

Fig. 20  a UV–visible spectrum and b fluorescence emission spectrum of ASDSN chromophore [64]

The shorter absorption peak at 365 nm-390 nm and < 350 nm excitation of the absorption maxima in the case of most sol-
indicated π-π* transition of pyrene and naphthalene moi- vents. Blue emission was result of π-π* transition of pyrene
eties respectively. Meanwhile the longer absorption peaks and naphthalene. The variation of fluorescence emission
at > 425 nm were due to n − 𝜋 ∗ transition of sulphonyl intensity of compound PSN was observed due to chang-
unit and −CH = N−. A blue color emission was observed ing solvent polarity because changing solvent environment,
for compound PSN at 445 nm-470 nm and 515 nm upon polarity and dipole moment also changed (Fig. 23) [65].

Fig. 21  Effect of pH on absorption spectra a and emission spectra b of the chromophore ASDSN [64]

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1288 Journal of Fluorescence (2023) 33:1273–1303

Fig. 22  synthetic route for the preparation of PSN [65]

Absorption Spectra of Naphthalene Based Dyes ­ iO2 film absorption,

While in the case of transparent thin T
YF01‑04 in Solution and Thin ­TiO2 Film all the dyes YF01-04 revealed similar absorption spectra
as showed in solution but miner blue shift was observed in
Four naphthalene based D-𝜋 -A organic dyes synthesized broad band which was assigned to the interaction of T ­ iO2
with electron donating unit amines and electron acceptor and carboxylic group. A red shift in the absorption spec-
unit cyanoacrylic substituted on naphthalene. The spectral tra tails for all the dyesYF01-04 was noticed in ­TiO2 film
properties of YF01-04 dyes were investigated on T ­ iO2film absorption as compared to spectra in solution. Extension
and in ethanol solution. The absorption spectrum showed of absorption tail up to 650 nm of dye YF04 was observed
maximum wavelength at about the range of 404 nm-423 nm which was responsible for large photocurrent [66].
which was assigned to π-π* transition of YF dyes as shown
in Fig. 24. Pyrrolidine based sensitizers YF04 and YF01
exhibited longer absorption wavelength in comparison to Effect of Substitution on UV–vis and Emission
sensitizer based on diphenylamine because the pyrrolidine Spectra of Arylamine‑substituted
had powerful electron donor capability as compared to Naphthalene Derivatives
diphenylamine. The dye YF02 displayed the highest value
of molar extinction coefficient whereas the molar extinction Two new molecules NH-2,6 and NH-2,7 were synthesized
coefficient values of all other dyes for maximum absorp- using naphthalene core as hole transporting material and
tion wavelength lies in the range of 1.1–3.2 M×104−1 ­cm−1. arylamine terminal group (Fig. 25).

Fig. 23  Solvent dependent UV–

visible absorption spectra of
PSN compound [65]

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Journal of Fluorescence (2023) 33:1273–1303 1289

Fig. 24  a Absorption spectra of dyes YF01-04 in solution and b in transparent thin T
­ iO2 film [66]

The normalized absorption and emission spectra were configuration. The optical energy bandgap were investigated
calculated in DCM solution. The absorption spectra of through interactions of normalized emission and absorp-
both compounds consist of two definite bands which were tion spectra which was 2.90 Ev for NH-2,6 and 3.00 EV for
clearly associated with intermolecular charge transfer char- NH-2,7 (Fig. 26).
acter (ICT) and to localized π-π* transition. In the absorp- Using time depended density functional theory (TD-DFT)
tion profile of NH-2,7, maximum absorption was observed the Homo and Lumo orbitals were calculated for both com-
at 352 nm.At the same time, by replacing 2,7-substituted pounds. It was observed that the HOMOs orbital density
naphthalene core with the 2,6-substituted core, the absorp- were totally localized over the entire molecular structure
tion band becomes more intense and also red shifted. The and acts as hole transporting materials for the promotion of
reason of this phenomenon could be assigned to highly hole carrier transport. At the same time, the LUMOs orbital
localization of π electron and stronger π-π* conjugation density mostly localized on the naphthalene core and less
between arylamine terminal and naphthalene core. Luckily addition of arylamine terminal on the conterminous phe-
the overlapped absorption was avoided with perovskite layer nyl ring. On the other hand, although the structure of both
as the absorption spectra did not lies in the visible range. In NH-2,6 and NH-2,7 were similar but the frontier molecular
fluorescence emission profile, the maximum emission of orbital density contribution in HOMO and LUMO descrip-
NH-2,6 was observed at 490 nm and peak of NH-2,7 was at tion was remarkably lower for NH-2,7 which was due to the
476 nm. These two compounds displayed large stock shifts interaction between 2,7-substituted naphthalene core and
which indicated that upon excitation these two molecules arylamine terminal hampers the effective molecule orbital
exhibits definite structural alternation in the geometrical overlap and further conjugation (Fig. 27) [67].

Fig. 25  NH-2,6 and NH-2,7

synthesized molecules having
naphthalene core [67]

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1290 Journal of Fluorescence (2023) 33:1273–1303

Fig. 26  The absorption and

emission spectra of NH-2,6 and
NH-2,7 [67]

Investigation of Different Electrical and Optical optimized ground state geometry. Through fronter molecu-
Properties of Cyclopentadithiophene‑ Naphthalene lar orbital plot it was observed that the dicyanomethylene
Derivatives using DFT Method bridge group from acceptor group was irregularly localized
on structure while HOMOs are dispersed on main conju-
Theoretical calculations were carried out on cyclopentadith- gated backbone. The substituted electron-withdrawing group
iophene- naphthalene derivatives owning smaller molecular fluoro and syano were enveloped by the HOMO distribu-
structure. Using DFT the effect of fluorine (-F) and cyano tions. The great displacement of HOMO in the structure
(-CN) as electron-withdrawing group on different electronic of these molecules proposed the charge transfer and higher
properties such as charge transfer, optical, electronic proper- electron delocalization.
ties and structural properties of the studies compound were The delocalization of electron inside the conjugated struc-
calculated. These calculations confirmed the rigid co-planer tured was better explained through density of state curve
structure. The fronter molecular orbitals analysis carried (DOS) which was carried out on the basis of optimized
out to examine electronic properties of the compound under ground state geometry. Higher localization of electron was
investigation. Utilizing the DFT/B3LYP/ 6-31 g(d) method demonstrated due to the overlapping of electronic energy
the highest occupied molecular orbital (HOMOs) and low- levels. The increase in localization indicated the mutual
est unoccupied molecular orbitals (LUMOs) were plotted at interaction of pi- spacer and donor- accepter (Fig. 28).

Fig. 27  Optimized structure

and HOMO–LUMO orbitals of
NH-2,6 and NH-2,7 [67]

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Journal of Fluorescence (2023) 33:1273–1303 1291

Fig. 28  Frontier molecular orbit-

als of studied compounds [36]

The band gap energies were at about 1.71 and 1.90 Ev for was incorporated on the naphthalene by phenyl or pheny-
SM1 and SM2 respectively. lethynyl moiety at C2 abs C7 (1a-4a) and methoxy group as
That miner band gap suggested the greater light harvest- weak donor moiety was introduced into naphthalene directly
ing ability of the compounds which would be utilized for the at the position opposite to the nitro group at the position
developing new and efficient OSC devices (Fig. 29) [36]. C3 and C6 (1b-4b) (Fig. 30). The introduction of a nitro
group into a fluorophore through a p-conjugated linker moi-
The UV–visible Absorption and Fluorescence ety such as a phenyl group is an effective method to induce
Emission Spectra of Nitro‑group‑containing fluorescence in a nitro-group-containing dye. Different pho-
Naphthalene Derivatives Having Weak Donor– tophysical properties of these synthesized compound were
strong Acceptor System calculated in various solvents. The group of solvents that
was used contain methanol, chloroform, dichloromethane,
New 𝜋 -congajuted naphthalene derivatives were synthe- toluene, tetrahydrofuran and acetonitrile.
sized by Hachiya et al. He used nitro containing 𝜋-conga- In the UV–vis absorption profile, for compound 1a the
juted naphthalene derivatives with strong acceptor and weak lowest energy band was located at about 320 nm in differ-
donor group. The nitro group as powerful acceptor moiety ent solvents. Absorption profile of 1a was taken as reference

Fig. 29  Density of state curve [36]

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1292 Journal of Fluorescence (2023) 33:1273–1303

Fig. 30  𝜋-congajuted structure of studied compounds [68]

and spectra for other compounds were compared with it. A brought on by the photoexcitation's fast distortion of the
remarkable red shift of about 20 nm was observed for 1b nitro group.
and 2a in comparison with 1a. This red shift was the clear While the solvatochromic fluorescence spectra indicated
indication of extension in the 𝜋-congajuted through methoxy a considerable reliance on the solvent polarity, the absorp-
and ethynyl group. Despite the fact that the lowest absorption tion spectra did not clearly demonstrate any influence on
maxima of bands 3 and 4 were nearly identical to those of
bands 1 and 2, the lowest-energy absorption bands of bands 3
and 4 had extinction coefficients that were in excess of those
of 1 and 2. These findings demonstrated that the p-electronic
conjugation system separates the donor–acceptor systems at
the C2-C6 and C3-C7 locations.
Only dichloromethane or chloroform could be used to
observe fluorescence in the cases of 2a and 4a, and the
fluorescence quantum yield was also extremely low. The
nitrophenyl-group-induced quick intersystem crossover
from a singlet excited state to a triplet excited state may
be the cause of the weak fluorescence of 1a–4a. Given that
1-nitronaphthalene exhibited no fluorescence under normal
circumstances, the linker technique was a successful way to
create fluorescence in nitronaphthalene derivatives (Fig. 31).
The Stokes shift of almost nitronaphthalene derivatives over Fig. 31  The absorption and emission spectra of 1a-4b in dichlo-
10,000 ­cm−1. This is due to a drastic shift in their structure romethane solvent [68]

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Journal of Fluorescence (2023) 33:1273–1303 1293

The hydrophobic naphthalene moiety with fluorogenic char-

acteristic could be employed as a component of an anion and
a cation sensor and to focus biomolecules. These groups
generate particular signals by specifically binding with ions
or targets through hydrogen bonding, electrostatic, and/or
hydrophobic interactions.
The solvatochromic effect of NNP ligand was studied in
different polar and non-polar solvents. The results showed
that absorption spectra exhibited bathochromic shift by
increasing solvent polarity (absorption wavelength shifted
to longer wavelength). Positive solvatochromism was indi-
cation of 𝜋 − 𝜋 ∗ transition due to intra molecular change
transfer. On the other hand, the fluorescence spectra also dis-
played solvent polarity dependent positive solvatochromism.
In alcohols and DMSO the red shifted emission was indi-
Fig. 32  UV–vis and emission spectra in different solvents [68] cation of photo induced intra molecular charge transfer in
singlet excited state of NNP. After that, anions sensing prop-
the solvent. The Stokes shift of 1b was extremely significant erty of NNP was found out using tetrabutylammonium salt
in all solvents, with a maximum value close to 306 nm in viz, ­Cl−, ­I−, ­Br−, ­SCN−, ­CIO4− and N­ O3− ions by changing
methaylcyanide. This value of Stokes shift was larger than absorption intensity in THF solution. It was observed that
unsubstituted nitronaphthalene derivatives. These findings among all above anions, only F- ion showed the naked eye
suggested that internal charge transfer (ICT) character was colorimetric effect as solutions color changed from yellow
generated by the addition of methoxy groups at the C2 posi- to brown. The absorption wavelength of NNP ligand was
tion. Similar solvatochromic fluorescence spectra and a sig- shifted from 415 to 470 nm by gradually increasing ions
nificant Stokes shift were seen for 2b and 4b (Fig. 32) [68]. concentration in NNP solution.
Two isobaric points were also observed at 350 nm and
425 nm indicating the formation of new products. These
isobaric points were not crossed by absorption spectra of
Naphthalene Based Fluorescence Probes NNP which confirmed that in the beginning hydrogen bond-
for Detecting/Sensing and Imaging Purposes ing takes place between F ­ − ion and NNP ligand, by further
−
increase in ­F ion concentration deprotonation occurs. How-
A Naphthalene‑based Schiff‑base Chemosensor ever ­Cl−, ­I−, ­Br−, ­SCN−, ­CIO4− and ­NO3− did not display
(NNP) for Multi Target Detection any remarkable changes in absorption spectra. These find-
ings confirmed the highest binding nature of F- ion to the
Gurusamy et al. synthesized this chemosensor by con- NNP as compared to other ions. Fluorescence titration was
densation reaction of N-phenyl-o-phenylenediamine and carried out by mixing different anions in THF solution of
2-hydroxy naphthaldehyde in one step (Fig. 33). N and NNP. By adding F- ion, remarkable improvement in emis-
O donor atoms in Schiff-bases result in intriguing com- sion of NNP at 545 nm was observed due to interaction of
pounds with transition metal ions. As a result, they have NNP and F- ion without significant shift (Fig. 34). But other
frequently been employed as chemosensors to detect metal anions did not significantly affect the emission spectra of
ions. Through deprotonation, the presence of an acidic N–H NNP legend. In these data, the colour of the NNP changed
allows for alternative binding modes for the various ions. from yellow to brown, indicating its superior colorimetric

Fig. 33  One-step synthesis of a

Schiff-base ligand, NNP [69]

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1294 Journal of Fluorescence (2023) 33:1273–1303

Fig. 34  Effect of F- ions on absorption and emission spectra of NNP [69]

sensitivity to the fluoride ion over other anions. The major curves at single point in absorption verses wavelength graph
practical applications of biological and environmental sens- is called isosbetic point [71]. The fluorescence experiments
ing investigations may benefit from the usage of this che- revealed that in the absence of Cys the BTNA probe solu-
mosensor [69]. tion showed almost no fluorescence. Addition of Cys into
the probe solution caused a radical alternation in the fluo-
A Naphthalene Based Fluorescence Probe (BTNA) rescence spectra. A new fluorescence peak was observed
for Bioimaging of Cysteine in Living Cells at 505 nm indicated the formation of BNO compound as
a result of BTNA probe reaction with Cys. Much larger
Zhang et al. synthesized a naphthalene based fluores- stocks shifts were observed up to 140 nm for this BTNA
cence probe named BTNA for Cysteine(Cys). Design of probe as compared to other identical probes. The probe itself
this naphthalene based probe was based on photo induced showed low fluorescence but fluorescence enhanced upon
electron transfer mechanism and it contains a fluorophore addition of Cys. Within 10 min, the fluorescence intensity
6-(2-benzothiazolyl)-2-naphthalenol (BNO) coupled with an became maximum (Figs. 36 and 37). Those findings con-
acrylate cluster (the fluorescence quenching and response firmed the highly sensitivity of probe BTNA towards Cys.
group) (Fig. 35). A linear relationship was obtained by changing concentra-
To investigate the spectral changes of BTNA probe for tion of Cys from 0 to 40 M𝜇 between emission intensity
Cys, UV–visible absorption and fluorescence spectroscopy and Cys as showed in Fig. 37b. This new probe has strong
were carried out in DMSO solution. In absorption spectra, a linearity ranges, a small Cys detection limit of 0.18 mM,
strong absorption peak of 330 nm wavelength was observed and a significant Stokes shift. In addition to these, it exhibits
for BTNA probe solution. Interestingly, this strong peak exceptional selectivity and sensitivity for Cys above other
decreased gradually with time by function of externally amino acids and common ions, such as the similarly struc-
added Cys into the solution. The peak at 330 nm shifted to tured homocysteine (Hcy) and glutathione(GHS), as a turn-
337 nm along with an isosbetic point which was located at on fluorescence probe. Last but not least, the probe BTNA
345 nm as shown in Fig. 36. The intersection of number of was successfully used to bioimage intracellular Cys in living

Fig. 35  Preparation of BTNA

probe [70]

13
Journal of Fluorescence (2023) 33:1273–1303 1295

Fig. 36  UV–visible spectra of

probe BTNA upon addition of
Cys [70]

Hela cells while exhibiting little cytotoxicity. Therefore, this N-chloroacetyl-1naphthylamine as shown in Fig. 38. The
probe can be employed as a new, effective research instru- selective binding and sensitivity action of small molecule
ment for applications involving the detection of Cys [70]. naphthalene based fluorescence probe BNBC were exam-
ined with the help of absorption and fluorescence spectros-
Selectivity of a Naphthalene Based Fluorescent copy. Two intensified absorption bands were observed in
Probe BNBC Towards Different Ions Especially ­Hg2+ the absorption spectrum of BNBC probe solution, one at
270 nm and other at 277 nm. Addition of ­Hg2+ ions caused
Wang et al. synthesized a new fluorescent probe named as highly remarkable alternation in the absorption profile of
BNBC having the naphthyl cluster to consecutive detecting the probe. As both absorption peaks were vanished and a
Hg2 + and I–. The fluoroscence probe BNBC was smoothly new absorption peak at 300 nm was created as a result of
produced by signle step using 1-benzylbenzimidazole and ­ g2+ ions. Upon the addition of C
externally added H ­ u2+ ions,

Fig. 37  The fluorescence titration of the probe BTNA with gradually addition of Cys from 0 to 100 μM (a) and linear relationship of F/F0 with
different concentrations of Cys (b) [70]

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1296 Journal of Fluorescence (2023) 33:1273–1303

Fig. 38  Scheme for the synthesis of BNBC [72]

a remarkable increment was observed in both absorption

peaks. However addition of N ­ a2+ ions caused a remark-
able increase in absorption intensity of 270 nm and miner
Fig. 40  Fluorescence spectra of BNCB probe upon addition of differ-
red shift in absorption intensity of second peak from 277 ent concentrations of ­Hg2+ [72]
to 286 nm. The solution of BNBC probe exhibited rep-
resentative fluorescence emission peak of 342 nm which
was associated with monomeric emission of naphthalene. with respect to concentration is called iso-emissive point
Upon treatment of BNBC probe with H ­ g2+ ions, naphtha- [71]. A linear relationship was observed between emis-
lene monomer emission band significantly decreased along sion intensity ratio and ­Hg2+ concentration. These findings
with a remarkable increase of naphthalene excimer emis- showed great sensitivity and selectivity of BNCB probe
sion at 428 nm. Whereas other metal species do not give towards ­Hg2+. The BNBC emission spectrum is drastically
any significant response to fluorescence spectra of the probe altered by the addition of Hg2 + , with the monomer emis-
BNBC(Fig. 39). sion being greatly reduced at the expense of an increase in
Addition of different concentrations of H ­ g2+ ions was the excimer emission. This may be because two BNBC mol-
made into the probe solution for understanding the metal- ecules coordinated with Hg2 + caused the two naphthalene
ion-binding feature of probe BNBC. It was observed that the units to form the excimer more tightly. BNBC-Hg2 + com-
excimers emission intensity of naphthalene gently increased plex exhibits a three-component ensemble-based selective
with increased concentration of H ­ g2+ and at the same time detection of ­I−. These findings suggested that this switch
monomers emission intensity decreased having clear iso- could be very useful for environmental and biological detec-
emissive point at 370 nm (Fig. 40). The point at which the tion applications [72].
intensity of excimer to monomer emission becomes linear

A Pyrene‑naphthalene Sulphonyl Conjugate (PSN)

as Sensing Probe

A new synthesized pyrene-naphthalene sulphonyl conju-

gated probe PSN consist of sulphonyl unit as electron with-
drawing group and naphthalene and pyrene unit as electron
donating groups. This probe was synthesized from 1-((1Z)-
(4-((Z)-4(pyrene-1-yl)methyleneamino)phenylsulfonyl)
phenylimino)methyl)naphthalene-2-ol (PSN) concluded two
step facial reaction (Fig. 41).
The compound is highly soluble in organic solvents and
insoluble in ethanol, methanol and water. Photophysical
properties of the compound PSN was due to the polarization
mechanism of chromophoric unit alkene, naphthalene and
pyrene (Fig. 42). The absorption spectra of compound PSN
displayed two types of transition dependent bands due to con-
jugation of electron donating and electron withdrawing groups.
Fig. 39  Fluorescence emission spectra of BNBC probe with addition
of various metal ions [72]
The shorter absorption peak at 365 nm-390 nm and < 350 nm

13
Journal of Fluorescence (2023) 33:1273–1303 1297

Fig. 41  synthetic route for the preparation of PSN [65]

indicated π-π* transition of pyrene and naphthalene moie- O–H group of PSN and H2PO4 formed a hydrogen bonding
ties respectively. Meanwhile the longer absorption peaks contact as part of the sensing mechanism. Additionally, dock-
at > 425 nm were due to n − 𝜋 ∗ transition of sulphonyl unit ing studies were performed on LYZ, and the results demon-
and −CH = N−. A blue color emission was observed for com- strate the importance of H-bonding and hydrophobic contacts
pound PSN at 445 nm-470 nm and 515 nm upon excitation of in LYZ's interaction with PSN. The fluorescent probe PSN is
the absorption maxima in the case of most solvents. Blue emis- intended to investigate additional research in the biosensing
sion was result of π-π* transition of pyrene and naphthalene. and bioimaging sectors. [65].
The variation of fluorescence emission intensity of compound
PSN was observed due to changing solvent polarity because Excimer Formation in Naphthalene Based
changing solvent environment, polarity and dipole moment Fluorescence Probe in the Presence ­Ni2+ as Living
also changed (Fig. 42). Different anions were used to test the Cell Imaging Probe
PSN's anion detecting capabilities. With a low detection limit
of 3.52 ×10−7 M and 7.23×10−7 M, respectively, H ­ 2PO−4 and A new fluorescence probe based on naphthalene 1-[(naphthalen-
−
­F ions were preferentially sensed among these anions, and 3-yl)methylthio]-2-[(naphthalen-6-yl)methylthio]-ethane
a clear colour shift from yellow to orange was observed. The (L) have been synthesized by Benerjee et al. The absorption

Fig. 42  Solvent dependent UV–

visible absorption spectra of
PSN compound [65]

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1298 Journal of Fluorescence (2023) 33:1273–1303

Fig. 43  Fluorescence emission

spectra of L representing forma-
tion of monomer and excimer [73]

spectrum of L influenced by externally added ­Ni2+ was inves- The simple probe L solution showed very low emission
tigated. The absorption spectra appears by increasing concen- intensity at 340 nm but gradual addition of ­Ni2+ caused
tration of ­Ni2+ in visible region from 370 to 460 nm having continuous increase at 430 m along with slightly high
low intensity band maxima at 420 nm with shoulder band at quantum yield at 340 nm. The emission at 430 nm was
about 345 nm. In mixture of DMSO-water solution L exhib- clearly due to naphthalene’s static excimer formation. Exci-
ited low quantum yield and emission of monomer at 345 nm tation at 345 nm in the L-Ni2+ system represented naph-
characterized by naphthalene moiety. By adding ­Ni2+ ions thalene monomer and naphthalene excimer in represented
into the solution, the emission of monomer of the naphthalene by excitation at 430 nm. A remarkable enhancement in the
moiety was quenched and at the same time excimer emission fluorescence intensity of L-Ni 2+ system assigned to the
intensity continuously increases along with the appearance of syn conformation between two naphthalene rings resent
an iso-emissive point located at 381 nm as shown in Fig. 43. in L-Ni.2+ system lead to the naphthalene based excimer

Fig. 44  Excimer formation of

L-Ni2+ system [73]

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Journal of Fluorescence (2023) 33:1273–1303 1299

Fig. 45  Structure of the probe

DMNDC where D(green) rep-
resent donor unit and A(pink)
represent acceptor unit [74]

formation (Fig. 44). As solitary monomeric emission was the solvents in the ground state of DMNDC is indicated
exhibited by free L probe, but in the existence of Ni2 + , by a peripheral shift of 2–8 nm in the solvent related
excimer formed by rotation of the C − C single bond. This absorption spectra, which is caused by the presence of a
probe could sense Ni2 + as low as 1 × 10 − 6 M associated modest dipole moment. However, electronic excitation
with strong binding constant of 2.0 × 104 M − 1. It is con- causes a greater difference in dipole moment between the
cluded that Ni2 + -filthy plant origin of living cell could excited state dipole moment and the ground state dipole
be imaged by means of a fluorescence microscope through moment, which is caused by the redistribution of charge.
this probe [73]. It facilitates in achieving a much better contact with the
solvents in the higher energy state, which results in the
Naphthalene Based Solvatochromic Fluorescence formation of a molecule's solvatochromism feature. The
Probe DMNDC Probe fluorescence spectra of DMNDC have nicely depicted
the substantial dependence in the fluorescence spectra
Mallick et al. synthesized a new non charge diethyl with varying solvent polarity. Improved stabilization of
6-(dimethylamino)naphthalene-2,3-dicarboxylate (DMNDC) the excited state in polar liquids is also made possible by
probe. The probe consist of the electron rich donor part and the molecule's increased dipole moment. Therefore, in
electron withdrawing part. The electron rich donor is N,N- polar solvents other than water, the fluorescence lifetime
dimethylamine unit and it is linked with two ester units of DMNDC is quite high and is influenced by other varia-
(electron withdrawing acceptor part) concluded conjugation bles such as hydrogen bonding ability (vide infra). Results
through a naphthalene unit as shown in Fig. 45. from determining the fluorescence lifetime of DMNDC
The purity of compound was confirmed by comparing in a number of different polar solvents provided evidence
the fluorescence and UV absorption spectra in DCM and in favour of this conclusion. Further research into vari-
water. The π-π* transition allowed absorption in ground ous micro-heterogeneous environments, such as globular
state and higher molar extinction coefficient. The varia- protein, vesicles, and supramolecular assemblies, can be
tion in solvent polarity did not cause any change in the done by utilising the electroneutrality, environment sen-
molar absorptivity and absorption maxima. The shoulder sitivity, and superior solvatochromic characteristics of
peaks of absorption spectra of DMNDC compound con- DMNDC [74].
formed poor solute–solvent interaction in ground state.
The red shift and broadening in the emission spectra of
DMNDC was observed by increasing polarity of solvent
as shown in Fig. 46. Upon increasing solvent polarity, the
emission maximum and stocks shift of DMNDC gradually
increased. The poor interaction of probe with different
solvents in ground state assigned to the smaller dipole
moment. Remarkably, with increasing solvent polarity,
both the Stokes shift and emission maxima of DMNDC
exhibit a consistent increment. This finding led us to the
realization that DMNDC can be employed to investi-
gate the nearby local microenvironment, which differs
greatly from the bulk solvent characteristics. Poor inter-
action with the solvents in the ground state of DMNDC
is indicated by a peripheral shift of 2–8 nm in the solvent
related absorption spectra, which is caused by the pres-
Fig. 46  Normalized emission spectra of probe DMNDC in different
ence of a modest dipole moment. Poor interaction with solvents [74]

13
1300 Journal of Fluorescence (2023) 33:1273–1303

different solvents and DMSO. That was indicated to remark-

able localized π-π* transition polarized with long z-axis of
NDI chromophore. Significant spectrum alterations with
notable hypochromicity were seen in aqueous solution, and
the formation of a new absorption band at 405 nm and band
widening both point to the presence of strong intermolecu-
lar p-p stacking between the NDI chromophores. In the FE
investigations, a very faint fluorescence band in DMSO was
found to correlate to the monomeric emission of NDI, with
an emission maximum at 408 nm (Fig. 48). Surprisingly, 1
in aqueous solution displayed a novel emission band (wide)
Fig. 47  Structure of the probe 1 [75] in the lower energy range (470–600 nm), with a maximum
at 540 nm. The charged to delocalize among the densely
packed NDI chromophores leads to excimer emission
A Green‑fluorescent π‑congajuted NDI Probe induced by the hydrophobic effect. It's interesting to note
for Detection of Organic Solvents that aromatic solvents had tunable fluorescence emission
characteristics in the visible spectrum, shifting from blue
Simple ethyl and amino acid groups (1A and 1B correspond to greenish yellow with maximum wavelength about 450,
to NDI with D- and L-alanine methyl ester functionality, 487, and 523 nm for benzene, toluene, and xylene, respec-
respectively) were used in the construction of asymmetri- tively with significant Stokes shifts. The lack of vibronic
cally functionalized 1 as imide substituents shown in Fig. 47. spectrum fluctuations in the UV–vis absorption spectra and
The functionalized The UV–visible absorption spectra the accompanying progressive red shift of the FE spectra
and fluorescence emission were conducted to find out the in aromatic solvents point to the presence of excited state
optical properties of the compound 1a compound in dime- interactions between the solvent and the fluorophor. This
thyl sulfoxide aqueous and different solvents such as ben- NDI molecular system can be employed for both fluores-
zene, xylene and toluene. Remarkable intense absorption cent aromatic solvent probes and organic multicolor displays
bands were observed in the range of 300-400 nm NDI in since it is optically highly sensitive to aromatic solvents [75].

Fig. 48  Absorption and emission spectra of the 1a compound in different solvents [75]

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Journal of Fluorescence (2023) 33:1273–1303 1301

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