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An AIE-active tetra-aryl imidazole-derived

chemodosimeter for turn-on recognition of
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Cite this: Org. Biomol. Chem., 2024,

22, 6135 hydrazine and its bioimaging in living cells†
Qing-Xiu Li, Yan-Ju Yuan, Rui-Xing Cheng, Yu Ma, Rui Tan, * Ya-Wen Wang *
and Yu Peng

A new chemodosimeter SWJT-31 with an aggregation-induced emission (AIE) effect was designed and
constructed. Upon increasing the water fraction in the solution, it exhibited typical AIE, which showed
Received 16th June 2024, bright red fluorescence at 610 nm. SWJT-31 could sensitively and specifically recognize hydrazine by the
Accepted 9th July 2024
TICT effect with an LOD of 33.8 nM, which was much lower than the standard of the USEPA. A portable
DOI: 10.1039/d4ob01009d test strip prepared using SWJT-31 was also developed for the visual detection of hydrazine. Eventually, it
rsc.li/obc was successfully used for the detection of hydrazine in water samples and HeLa cells.

Introduction enemalononitrile,11–14 condensation of hydrazine and alde-

hydes or ketones,15 deprotection of acetyl groups and their
Hydrazine (N2H4) is a colorless oily liquid with a pungent derivatives,16–18 and hydrazine-induced cyclization or ring-
smell similar to ammonia. Because of its superior chemical opening reactions.19–22 Unfortunately, the fluorescence of
properties, hydrazine is widely used in the production process these hydrazine identification probes is easily quenched in
of pesticides, pharmaceuticals, emulsifiers and polymer aqueous solutions or in the solid state due to the aggregation-
foams.1,2 It is also used as an accelerant and high-energy fuel caused quenching (ACQ) effect, which greatly limits their
in aerospace.3 Hydrazine is highly volatile and easily soluble in application. In 2001, Tang’s team23 reported the phenomenon
water, so it inevitably causes serious pollution of water, soil of aggregation-induced emission (AIE), which effectively
and air. There is no endogenous production of N2H4 in living addresses the defects present in ACQ fluorescent probes. The
systems,4 but humans and animals can absorb N2H4 through advantages of AIE molecules in the aggregated state are large
skin, breathing and mucous membrane contact. Moreover, Stokes shifts, high fluorescence quantum yields, and excellent
commonly used drugs such as isoniazid are also metabolized resistance to photobleaching because the intramolecular
to produce hydrazine in the body.5 When hydrazine enters the motion of the rotor-containing AIE luminogens is restricted in
living body, it can cause serious damage to the kidneys, body’s the aggregated state, and the excited state energy is mainly
central nervous system, liver and lungs.6–8 As a result, the consumed by radiation.24,25 Therefore, the application of AIE
United States Environmental Protection Agency (USEPA) has fluorescent probes in environmental detection, biomedical
announced that the threshold limit for residues of N2H4 in imaging and other fields has aroused strong research
drinking water should be less than 10 ppb (0.312 µM).9,10 interest.26–29 At present, several AIE fluorescent probes30–38 for
Therefore, it is of great value to develop new methods that the detection of hydrazine have been reported (Table S1, ESI†),
could be used to detect hydrazine in the environment or living but most of them have long response times, high detection
organisms. limits, and require a higher organic phase as the test solution.
At present, most fluorescent probes for the detection of Therefore, it is urgent to develop AIE-based fluorescent probes
hydrazine are based on the following reaction mechanisms: with a high water ratio, high sensitivity, and a short response
nucleophilic substitution of hydrazine for methyl- time to detect N2H4.
To the best of our knowledge, no AIE fluorescent probe
with tetraaryl imidazole39–41 as the skeleton for the recognition
School of Chemistry, School of Life Science and Engineering, Southwest Jiaotong of hydrazine has been reported. In connection with our
University, Chengdu 610031, People’s Republic of China. research on AIE probes,42 herein, a new fluorescent probe
E-mail: [email protected], [email protected]
SWJT-31 with an AIE effect based on the tetraaryl imidazole
† Electronic supplementary information (ESI) available: Spectral data, copies of
1
H/13C NMR, ESI-MS and other materials can be found in the online version. See skeleton was synthesized, which could recognize hydrazine by
DOI: https://doi.org/10.1039/d4ob01009d the TICT (twisted intramolecular charge transfer) effect. Its

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Paper Organic & Biomolecular Chemistry

fluorescence was very weak in a low water phase solution.

However, SWJT-31 could emit bright red fluorescence in a high
water phase solution ( fw ≥ 70%) due to the formation of aggre-
gates, which belonged to the typical AIE luminous body.30
When the water fraction was less than 50% ( fw ≤ 50%), Scheme 2 Synthesis of SWJT-31.
SWJT-31 had a significant blue-green fluorescence enhance-
ment response to hydrazine. Moreover, a portable test strip
using SWJT-31 was developed and successfully used for the shown in Fig. 1, when the fraction of H2O was low, SWJT-31
detection of hydrazine in water samples and living cells. only had weak fluorescence at 610 nm, while when the fraction
of H2O was increased to 70%, its fluorescence was significantly
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enhanced. Importantly, when the fraction of H2O was

Results and discussion increased to 80%, the fluorescence intensity reached its
Design and synthesis of SWJT-31 maximum. To further determine whether SWJT-31 formed
aggregates in the aqueous solution, dynamic light scattering
To study the tetraaryl imidazole fluorophore with an AIE (DLS) was investigated. As shown in Fig. S6 (ESI†), there were
effect,43 the probe SWJT-31 was constructed. As shown in particles with an average size of 75.03 nm, which indicated
Scheme 1, the structure of the probe was a donor–π–acceptor that SWJT-31 formed stable aggregates.47 These results identi-
(D–π–A) system: the tetraaryl imidazole group acted as the elec- fied that the probe had AIE characteristics.
tron donor and the malononitrile unit as the acceptor. The
donor and acceptor were connected by a freely rotatable single
bond, and their photophysical properties could be obtained by Sensing properties
adjusting the intramolecular charge transfer (ICT) ability of In order to find the optimal test system for SWJT-31, the fluo-
the acceptor and donor. The activation of the ICT process may rescence changes in SWJT-31 before and after adding hydra-
be accompanied by significant changes in molecular geometry, zine were studied. In different organic solutions, different
leading to a TICT state.44 To confirm the TICT effect of buffer solutions, and different mixture solutions and under
SWJT-31, its fluorescence behavior was studied in different different pH conditions, the fluorescence of SWJT-31 was
DMSO–glycerol compositions. As shown in Fig. S4 (ESI†), the studied in detail (Fig. S7–S10, ESI†). Based on these results
emission of SWJT-31 gradually increased upon adding high- and considering its application in biological systems, DMSO/
viscosity glycerol to the DMSO solution. These results indi- HEPES solution (v/v = 6 : 4, pH = 7.4) was selected as the test
cated that the probe has an obvious TICT effect. Therefore, system for subsequent studies.
SWJT-31 exhibited weak fluorescence emission. However, the Subsequently, the spectral response of SWJT-31 to N2H4
probe reacted with N2H4, the electronic push–pull effect on the was investigated. As shown in Fig. 2a, SWJT-31 had a signifi-
probe changed, and the TICT effect weakened, which may lead cant absorption peak at 355 nm, while the peak shifted to
to the enhancement of fluorescence emission.45 The synthetic about 340 nm after adding hydrazine to the solution. The
route of SWJT-31 is shown in Scheme 2, and the structure of color of the solution changed from faint yellow to colorless
the probe was confirmed by NMR spectroscopy and LC-MS under visible light (Fig. 2a, inset). In addition, the fluo-
(Fig. S1–S3, ESI†). rescence spectrum is shown in Fig. 2b. Under excitation at
340 nm, SWJT-31 showed weak fluorescence at 453 nm, while
AIE properties of SWJT-31 after adding hydrazine, the maximum emission peak of the
SWJT-31 was soluble in DMSO, but almost insoluble in water, solution changed from 453 nm to 497 nm, and the fluo-
so the AIE performance of SWJT-31 was determined by increas- rescence intensity at 497 nm was increased about 25 times.
ing the water fraction.46 In order to determine the excitation Obviously, the color of the solution changed from dull yellow
wavelength of the AIE channel, the absorption spectra of
SWJT-31 in 99% HEPES solution were studied (Fig. S5, ESI†).
The maximum absorption band of SWJT-31 was centered at
about 420 nm, which was used as the excitation wavelength. As

Fig. 1 (a) Fluorescence spectra of SWJT-31 (10.0 μM) in DMSO/HEPES

buffer solution ( pH 7.4) with different water fractions. (b) Fluorescence
intensity of SWJT-31 (10.0 μM) at 610 nm versus the water fraction in
Scheme 1 The N2H4 sensing mechanism of SWJT-31. DMSO/HEPES buffer solution ( pH 7.4, λex = 420 nm).

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Fig. 2 (a) Absorption spectra and (b) fluorescence spectra of SWJT-31

Fig. 4 Fluorescence spectra of SWJT-31 (10.0 µM) with different ana-
(10.0 μM) in the absence and presence of N2H4 (100.0 μM) in DMSO/
lytes (100.0 µM). (b) SWJT-31 (10.0 µM) to identify N2H4 anti-inter-
HEPES buffer solution (v/v = 6 : 4, pH = 7.4, λex = 340 nm). Inset: the
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ference with different analytes (100.0 µM), among which are blank,
corresponding photographs of SWJT-31 (10.0 μM) in the absence or
hydrazine, triethylamine, aniline, n-butylamine, NH4+, Na+, K+, Mg2+,
presence of N2H4 (100.0 μM) under (a) room light and (b) 365 nm UV
Zn2+, Cys, Hcy, GSH, ClO−, HCO3−, NO2−, SO42−, Br−, S2−, urea, H2O2,
light.
ONOO−, Ser, Trp, Leu, and Glu (λex = 340 nm).

to bright blue-green under 365 nm UV light (Fig. 2b, inset). When bisulfite ions were added to the solution of SWJT-31,
Accordingly, SWJT-31 with the AIE effect could be used as a fluorescence at 440 nm was observed (Fig. S11, ESI†). However,
turn-on fluorescent probe for hydrazine.36 bisulfite ions are found in extremely low amounts in normal
To explore the sensitivity of SWJT-31 in the detection of organisms, so they hardly affect the cellular imaging of exogen-
hydrazine, concentration titration experiments were carried ous hydrazine. Obviously, the addition of other analytes hardly
out. As shown in Fig. 3a, the fluorescence intensity at 497 nm changed the fluorescence of SWJT-31. Then, the anti-jamming
also enhanced as the N2H4 concentration increased. As can be capabilities of SWJT-31 were investigated. As can be seen from
seen from Fig. 3b, N2H4 concentrations in the range of 0 to Fig. 4b, SWJT-31 responded sensitively to N2H4 in the presence
14.0 μM and fluorescence intensity at 497 nm exhibited a good of other analytes. These results showed that SWJT-31 possesses
linear relationship. The linear regression equation is obtained good selectivity and anti-interference performance for the
as: Y = 20.9933X + 116.5619 (R2 = 0.9991). According to the detection of hydrazine in complex environments.
LOD and LOQ calculation formula,48 the limits of detection In addition, the time-dependent fluorescence response of
(LOD) and the limits of quantification (LOQ) of SWJT-31 for SWJT-31 to N2H4 was also tested. As shown in Fig. S12 (ESI†),
N2H4 were calculated to be 33.8 nM and 0.11 μM, respectively, the fluorescence of SWJT-31 was weak and the emission inten-
which were well below the USEPA’s standard of 0.312 μM. The sity was stable at 497 nm. Obviously, the fluorescence of
above results showed that SWJT-31 could identify N2H4 with SWJT-31 + N2H4 was sharply enhanced within 4 min and
high sensitivity by changing the fluorescence emission almost reached equilibrium within 30 min. According to the
intensity. above results, the pseudo-first-order kinetics equation diagram
Selectivity and anti-interference are important to evaluate of SWJT-31 for N2H4 was drawn (Fig. S13, ESI†). The kobs of
the application of the probe, so the fluorescence responses of SWJT-31 was calculated to be 9.06 × 10−4 s−1, and t1/2 was
SWJT-31 to common amines, biothiols, various anions and 12.74 min.49 These results indicated that SWJT-31 could
cations, and reactive oxygen species were investigated. As respond to hydrazine quickly in aqueous solution.
shown in Fig. 4a, the fluorescence intensity of SWJT-31 was
significantly enhanced at 497 nm only after hydrazine was
added. The fluorescence intensity of the probe increased
Proposed mechanism
slightly at 440 nm after the addition of S2−, but the enhance-
ment at 497 nm was much smaller than that of hydrazine. According to the proposed reaction mechanism,36 the malono-
nitrile electron-withdrawing group on SWJT-31 may be
replaced by N2H4 nucleophiles to form product SWJT-N2. To
identify this hypothesis, a round-bottom flask experiment was
carried out, and SWJT-N2 was isolated and purified from the
mixture after the reaction of SWJT-31 with N2H4. The structure
of SWJT-N2 was characterized by 1H NMR, 13C NMR and
LC-MS (Fig. S14–S16, ESI†). As shown in Fig. 5, the Ha signal
of SWJT-31 occurred at 7.7 ppm, while the Ha′ signal of
SWJT-N2 migrated to a higher field at 7.5 ppm. Significantly, a
new amino proton signal Hb appeared at 5.5 ppm.
Furthermore, the mass spectrum of SWJT-N2 is shown in
Fig. 3 (a) Fluorescence spectra of SWJT-31 (10.0 μM) in the presence
of different concentrations of N2H4 (0–100.0 μM). (b) Relationship
Fig. S13,† and its ion peak appeared at m/z 475.2 [M + H]+.
between the fluorescence intensity at 497 nm and the N2H4 concen- These results showed that SWJT-N2 was the product of
tration (λex = 340 nm). SWJT-31 and N2H4.

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Application of SWJT-31 in water samples

N2H4 causes strong pollution and toxicity, and its application
in industry and agriculture may cause pollution in the sur-
rounding environment and water sources. Therefore, it is of
great significance to detect the content of N2H4 in water
samples. Next, tap water, Jing-hu Lake water, and fountain
spring water were selected as the test water samples to deter-
mine the concentration of N2H4 using SWJT-31. As shown in
Table S2 (ESI†), SWJT-31 still showed a sensitive response to
N2H4 in these water samples, and the recovery rates of N2H4
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ranged from 86.9% to 107.4%, which indicated that SWJT-31

could detect N2H4 in water samples.
Fig. 5 The proposed mechanism of SWJT-31 with N2H4 and partial 1H
NMR spectra in CDCl3. (a) SWJT-N2 and (b) SWJT-31 only.

Application of SWJT-31 as a test strip

DFT calculations Considering the practical application of SWJT-31, a portable
To further confirm the sensing mechanism of SWJT-31, hydrazine test strip was prepared by impregnating the probe
density functional theory (DFT) calculations were performed onto filter paper. Then, N2H4 was evenly sprayed onto the strip
using Gaussian-09 software and the B3LYP/6-31G method. As in a concentration gradient. As shown in Fig. 7, under the
shown in Fig. 6, the electron cloud of SWJT-31 was mainly dis- irradiation of a 365 nm UV lamp, with an increase in the con-
tributed on the arylimidazole structure of the electron donor centration of hydrazine, the fluorescence color of the test strip
in the HOMO, while it was mainly concentrated on the changed from dull yellow-green to gray-green and then to
malononitrile unit (electron-withdrawing part) in the LUMO. bright blue fluorescence. These results showed that SWJT-31
The donor and acceptor were connected by a single bond that could be successfully prepared into portable strips for prelimi-
could rotate freely. According to the above results and related nary visualization of different concentrations of N2H4.
reports,44 SWJT-31 should have weak fluorescence due to the
strong TICT effect. In contrast, the electron-absorbing part
changed from the malononitrile group in SWJT-31 to the phe- Cell imaging
nylhydrazone unit in SWJT-N2, and the electron clouds were To investigate the imaging effect of SWJT-31 in vivo, confocal
more evenly distributed in the HOMO and LUMO, which fluorescence imaging results were evaluated before and after
would weaken the TICT effect of the probe leading to a large the addition of N2H4 to the probe in HeLa cells. Before the
enhancement of fluorescence. In addition, the calculated experiments, the cytotoxicity of SWJT-31 to HeLa cells was
energy gap of SWJT-31 (Egap = 2.515 eV) was smaller than that measured by the MTT assay at concentrations ranging from 0
of SWJT-N2 (Egap = 3.680 eV), which indicated that the pres- to 20.0 μM. SWJT-31 had good biocompatibility and could be
ence of N2H4 would lead to a blue shift in the absorption spec- used in cell imaging experiments at the required probe con-
trum. These results were consistent with the changes in the centration for cell imaging (Fig. S17, ESI†). As shown in
photophysical spectrum. Fig. 8a–h, SWJT-31 showed strong fluorescence in the red
channel after incubation with HeLa cells, while fluorescence
was almost invisible in the green channel, because the content
of ambient water in the cell was high, which stimulated the
AIE effect of the probe. After the addition of N2H4, the fluo-
rescence in the red channel almost disappeared, and the fluo-
rescence in the green channel was significantly enhanced.
These studies indicated that SWJT-31 could be used for the
detection of exogenous hydrazine in living cells.

Fig. 6 Optimized structures, molecular orbital surfaces, and the Fig. 7 Photographs of SWJT-31 filter paper sprayed with different con-
HOMO–LUMO energy level plots of SWJT-31 and SWJT-N2. centrations of N2H4 (0–3.0 mM) under 365 nm UV irradiation.

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