Journal of Molecular Structure 1289 (2023) 135941

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Journal of Molecular Structure

journal homepage: www.elsevier.com/locate/molstr

A fluorescent “off-on-off” probe based on a new bis(salamo)-like compound

for the sensitive and rapid detection of phosphates
Le-Chuan Feng, Xiao-Xia Li, Rui Chen, Li-Li Man, Wen-Kui Dong *
School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou, Gansu 730070, PR China

A R T I C L E I N F O A B S T R A C T

Keywords: A new bis(salamo)-like compound H3L was designed and synthesized. With the addition of Zn2+ ions to the H3L
Complex sensor solution, the fluorescence intensity increased significantly and the color changed from blue-cyan to bright green.
Ligand substitution mechanism Based on ESI-MS, UV–Vis spectroscopy and DFT calculations, a plausible mechanism for the interaction of the
Fluorescence sensor
compound H3L with Zn2+ ions is proposed. The in situ complex sensor L-Zn2+ formed by the coordination of the
Phosphate
Off-on-off
compound H3L with Zn2+ions has been used for various anion recognition. The results showed that the sensor L-
Zn2+ has high selectivity and sensitivity to phosphates. The fluorescence experiments of the compound H3L and
sensor L-Zn2+ at different pH values showed that fluorescence response is good in neutral and weak base envi­
ronment. Simple test paper strips and the detection in real water samples were applied for the detection of
phosphates in complex environment.

1. Introduction [14,15]. As novel Schiff base compounds, salamo-like compounds are

more stable than salen-like compounds through the introduction of ox­
Phosphate anions are important components in living organisms and ygen atoms on the C=N bonds [16]. Due to their strong chelating abil­
can participate in processes such as DNA construction, energy storage ities, salamo-like compounds are more easily coordinated with metal
and information transcription [1]. In addition, phosphate compounds (II/III) ions to achieve the detection of metal(II/III) ions [17–21]. Up to
are one of the main causes of water eutrophication [2]. Because the now, the research of salamo-like compounds have expanded from the
phosphate root and its derivatives are so important, the identification symmetric structure to asymmetric structure, as well as C-type bis
and detection of such substances have received widespread attention. (salamo)-like compounds [22–26]. This provides a broad view for
Although many studies have been reported [3–5], how to recognize designing the molecular structures of chemosensors.
phosphate sensitively, selectively and specifically is still a challenging Halogen atoms can enhance intermolecular C-X⋅⋅⋅π (X = Br, Cl) in­
work. Compared with other ion detection methods, fluorescent chemical teractions, which contribute to the intermolecular aggregation behavior
sensors have attracted more attention because of their high sensitivity of fluorescence sensors. In addition, halogen atoms can be used as
and real-time detection. The development of ion fluorescence chemical electron absorption groups to regulate the electronic properties of
sensors with high selectivity has become a research hotspot [6,7]. At traditional salamo-like compounds. In 2016, Dong et al. reported that
present, many anions cannot be directly detected using fluorescent the fluorescence emission performance of chemical sensor was regulated
sensors, while other detection methods are limited. The recognition through modification with chlorine substituents, achieving the detection
mechanism of the anion is usually carried out through the ligand sub­ of Zn2+ ions [27]. In 2023, Hu et al. designed a multi-halogen modified
stitution mechanism [8–10]. For example, the in situ complex sensor is half-salamo-like chemical sensor with AIE effect, achieving continuous
formed when the ligand molecule is coordinated with the metal ions. detection of Cu2+and S2- [3]. Based on previous researches, a new bis
Because of the strong complexing ability of anions and metal ions, the (salamo)-like compound H3L with two coordination cavities was syn­
ligand molecule is released from the in situ complex sensor and the thesized from 2‑hydroxy-5-methylisophthalaldehyde and 2-[O-(1-eth­
fluorescent signal is restored, thus achieving anion detection [11–13]. yloxyamide)]oxime-4-chlorophenol. In excited state, H3L exhibits C=N
Schiff base units are often used to build fluorescence sensors because bond isomerization, resulting in weak fluorescence emission intensity
the nitrogen atoms in Schiff base also have strong affinity for metal ions [28]. When it coordinates with specific metal(II/III) ions, the

* Corresponding author.
E-mail address: [email protected] (W.-K. Dong).

https://doi.org/10.1016/j.molstruc.2023.135941
Received 15 April 2023; Received in revised form 19 May 2023; Accepted 3 June 2023
Available online 4 June 2023
0022-2860/© 2023 Elsevier B.V. All rights reserved.
L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

2.2. Synthesis of the compound H3L

The synthetic route of the compound H3L is mainly performed by

Scheme 1. Compound 1,2-bis(aminooxy)ethane was synthesized on the
basis of previous reports [30]. The preparation process is as follows. An
ethanol solution (60 mL) of 5‑chloro-salicylaldehyde (782.85 mg,
5.0000 mmol) was added dropwise to an ethanol solution (30 mL) of 1,
2-bis(aminooxy)ethane (690.75 mg, 7.5000 mmol) at 55–60 ◦ C under
magnetic stirring and water bath heating, and the stirring was keeping
for 5 h. The resulting mixture was distilled under reduced pressure to
obtain the mixture of 5‑chloro-salicylaldehyde mono- and
di-condensation compounds (by-products). The above mixture was
separated by column chromatography with trichloromethane/ethyl ac­
etate (V/V = 15:1) as the eluent. Finally, the obtained liquid solution
was evaporated under reduced pressure, then recrystallized from
dichloromethane/n-hexane (V/V = 1:9) to obtain the white solid com­
pound 2-[O-(1-ethyloxyamide)]oxime-4-chlorophenol. Yield: 60.2%
(694.25 mg, 3.0000 mmol).
An ethanol solution (60 mL) of 2‑hydroxy-5-methylisoph­
thalaldehyde (164.20 mg, 1.0 mmol) was added directly to an ethanol
Fig. 1. Fluorescence intensity plots generated by adding various metal cations solution (60 mL) of 2-[O-(1-ethyloxyamide)]oxime-4-chlorophenol
to the solution containing the compound H3L in DMF/H2O (9/1, v/v, pH = (461.30 mg, 2.0000 mmol) at 55–60 ◦ C under the condition of magnetic
7.4) system. stirring and water bath heating. After the reaction carried out for 24 h, a
large amount of white flocculent solid was precipitated from the mixed
isomerization of the C=N bond is inhibited, the stiffness increases, and solution, which was filtered and dried to obtain a white solid H3L. Yield:
fluorescence is greatly enhanced, which helps to detect specific metal 75% (442.07 mg, 0.75000 mmol). M.p. 140–142 ◦ C. 1H NMR (500 MHz,
(II/II) ions [29]. It is worth mentioning that compared to previous Chloroform-d) δ 9.95 (s, 1H), 9.77 (s, 2H), 8.36 (s, 2H), 8.16 (s, 2H),
salamo-like sensors that recognize phosphates, this sensor has fewer 7.29 (s, 2H), 7.21 (s, 2H), 7.12 (s, 2H), 6.92 (s, 2H), 4.49 (s, 8H), 2.28 (s,
synthesis steps, mild reaction conditions, and high yield. Experimental 3H) (Fig. S1). 13C NMR (126 MHz, Chloroform-d) δ 155.92, 153.54,
results confirmed that H3L exhibits a marked fluorescence enhancement 150.92, 148.51, 130.96, 130.72, 129.78, 128.85, 124.20, 118.15,
towards Zn2+ions. Then, the resulted Zn(II) complex sensor L-Zn2+ has a 117.90, 117.23, 73.24, 72.61, 20.12 (Fig. S2). ESI-MS calculated for
fluorescence quenching behavior toward phosphates. C27H26Cl2N4O7: 589.43 [M], Found: 588.10 [M-H]− (Fig. S3). Anal.
calcd. for C27H26Cl2N4O7 (%): C, 55.02; H, 4.45; N, 9.51. Found: C,
2. Experimental section 55.33; H, 4.36; N, 9.40.

2.1. Materials and measurements

2.3. Synthesis of the complex sensor L-Zn2+solution

Details of materials and measurements were transferred to Sup­

In DMF solution (10 mL), the compound H3L (29.47 mg, 5.0 × 10− 2
porting material.
mmol) was fully stirred with Zn(NO3)2⋅6H2O (29.75 mg, 1.0 × 10− 1
mmol) to produce the sensor L-Zn2+ solution (5.0 × 10− 3 M). ESI-MS
calculated for C27H23Cl2N4O7Zn2: 717.16 [M]+, Found: 773.22 [M +
K+OH]+ (Fig. S4).

Fig. 2. (a) Fluorescence spectra of the compound H3L with increasing Zn2+ concentrations (Insets: fluorescence color of H3L with and without Zn2+ ions under a 365
nm UV lamp); (b) Fluorescence intensity plots of the compound H3L with Zn2+ ions at different pH conditions (λex= 372 nm).

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L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

Table 1 2.5. Theoretical calculations

The binding ratio of related salamo-like ligands to metal ions.
Related salamo-like compounds metal ions binding ratio Ref. Gaussian 16 Program [31,32] was used for Density functional theory
2+ calculations. The orbital energy distribution of H3L and L-Zn2+were
Zn 1:2 [34]
calculated at the B3LYP level. 6–31+G(d,p) (for H3L) and SDD basis sets
(for L-Zn2+) were used for calculation.

2.6. Preparation of filtered paper strips for practical application

Pre-treated paper strips [33] were immersed in the H3L solution (5.0
× 10− 5 M) for 10 min, then removed and dried in air.

Zn2+ 1:2 [35] 3. Results and discussion

3.1. Fluorescence behavior of the compound H3L

Conducting an aqueous system test for the compound H3L, it was

found that the lower the water content, the higher the fluorescence in­
tensity (Fig. S5). This may be due to the insolubility of the compound
H3L in water. Therefore, the fluorescence is directly quenched when the
water content exceeds 90%. However, when the water content is below
Cu2+ 1:2 [24] 40%, the compound H3L has fluorescence. This indicates that the pres­
ence of an appropriate amount of water does not seriously affect the
fluorescence intensity of the compound H3L, which is also very condu­
cive to ion detection in real environments [18]. In order to obtain
excellent fluorescence properties as much as possible, DMF/H2O (9/1,
v/v, pH = 7.4) system was selected as the substrate solution for testing.
To evaluate the fluorescence characteristics of the compound H3L for
metal ions, the fluorescence spectra of the compound H3L were recorded
Cu2+ 1:2 [36] after adding 10 equiv. of various metal ions (Zn2+, Al3+, Ba2+, Ca2+,
Cd2+, Co2+, Cr3+, Cu2+, Fe3+, Hg+, Hg2+, K+, Li+, Mg2+, Mn2+, Ni2+,
Pb2+, Sr2+, Ag+ ions). As shown in Fig. 1, no significant fluorescence
changes were detected when other metal ions were added to the DMF/
H2O (9/1, v/v, pH = 7.4) solution of the compound H3L (5.0 × 10− 5 M)
(except Zn2+ and Cd2+ ions, which showed fluorescence enhancement
effects). Zn2+ and Cd2+ are located in the same group of the periodic
table, therefore exhibiting similar fluorescence properties. Among
salamo-like compounds, due to chelation enhanced fluorescence, the
Cu2+ 1:2 [25] addition of Zn2+and Cd2+ ions usually lead to enhanced fluorescence of
compounds. Therefore, when 10 equiv. of Zn2+ ions were added, sig­
nificant fluorescence enhancement was recorded.
The relationship between the emission intensity of the compound
H3L and the concentration of Zn2+ ions was determined by fluorescence
titration experiments. As shown in Fig. 2a, the emission intensity
increased gradually after adding Zn2+ ions to H3L (5.0 × 10− 5 M) so­
lution, and the emission intensity at 488 nm reached the maximum with
adding Zn2+ ions 2.0 equiv. Additionally, the color of the compound H3L
changed from blue-cyan to bright green as the Zn2+ ions were gradually
added under the 365 nm UV lamp (Fig. 2a). The emission wavelength of
2.4. Preparation of ion recognition stock solution H3L is 509 nm, and as its concentration increases, its emission color also
changes from blue-cyan to bright green (Fig. S6). This may be the reason
The stock solutions of the compound H3L were prepared in DMF. The why the addition of Zn2+ ions causes the change of emission color, but
cations and anions were prepared respectively in deionized water as the emission wavelength does not change much. The dependence of the
stock solutions. All metal ions were prepared using nitrates. In all compound H3L on the pH value was investigated in a fluorescence test
fluorescence spectroscopy tests, without specification, the concentration and the results are shown in Fig. 2b, which indicates that the compound
of the compound H3L and sensor L-Zn2+ is 5.0 × 10− 5 M, and ions is 1.0 H3L is stable for the fluorescence opening of the Zn2+ ions at least in the
× 10− 4 M. The total concentration of H3L and Zn2+ in the solution was pH 6 to 12.
kept constant (5 × 10− 5 M) for the Job’s plot measurement. All spectral According to the results of the fluorescence titration experiment,
tests were carried out in DMF/H2O (9/1, v/v, pH = 7.4) solution system. combined with the Benesi-Hildebrand equation (Eq. S1), the binding
It should be noted that because the fluorescence intensity of the solution constant value (Ka) of the compound H3L to Zn2+ ions was calculated as
is susceptible to concentration, instrument sensitivity, fluorescence 4.7 × 104 M− 1 [28]. The Ka values of Zn(II) complexes with bis
wavelength scanning setting conditions, substance mixing uniformity, (salamo)-like ligands were listed in Table S1. The Benesi-Hildebrand
operation error. Therefore, all fluorescence intensity in this work is fitting line based on the fluorescence titration of Zn2+ ions with H3L is
relative fluorescence intensity. shown in Fig. S7. The binding ratio of the compound H3L to Zn2+ ions
may be speculated by reference to the binding ratio of related
salamo-like ligands to metal ions, UV–Vis titration experiment (When

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L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

Fig. 3. (a) UV–Vis titration spectral changes of Zn2+ions toward the compound H3L; (b) Job plot for binding ratio between H3L and Zn2+ions.

0.1 equivalents of Zn2+ ions were added to the H3L solution, a new calculated to be 3.91 × 10− 8 M (Eq. S2). The linear fit plot of the min­
absorption peak was suddenly generated in the wavelength range of imum detection is shown in Fig. S9. In order to apply the sensor L-Zn2+ to
350–460 nm. Then, with the addition of Zn2+ ions, the absorption peak more complicated environments, its range of applicability at different
gradually decreases until it reaches 2 equivalents), Job working curve pH values was investigated. The variation of the fluorescence intensity
and ESI-MS spectrum (Table 1, Figs. 3a, b and S4). Experimental results of L-Zn2+ in the presence and absence of H2PO−4 in the system with pH 2
confirmed that the possible binding ratio is 1:2. to 13 is shown in Fig. 4d. The results showed that the sensor L-Zn2+
As shown in Fig. S8, the fluorescence competition experiments of the exhibits good detection ability in neutral and weak alkaline system.
compound H3L toward Zn2+ ions showed the metal ions Al3+, Cr3+, Furthermore, the response specificity of L-Zn2+ to other inorganic
Cu2+, Fe3+, Hg+, Hg2+, Ni2+, Pb2+ has serious disturbance to the iden­ phosphate species (HPO2− 4 ) was investigated (Because sodium phos­
tification of Zn2+ions. The experimental results showed the compound phate is very easy to decompose into disodium hydrogen phosphate
H3L is not suitable for Zn2+ions specific identification. However, in situ when it meets water, in order to ensure the rigor and authenticity of the
complex sensors L-Zn2+ formed by the combination of Zn2+ ions and the experiment, sodium phosphate was not added). Due to the dynamic
compound H3L can be used to identify anions. reversible reaction between H2PO−4 and HPO2− 4 , it is actually difficult to
conduct specific detection between solutions of H2PO−4 and HPO2− 4 . As

3.2. The sensing and selectivity studies of L–Zn2+ probe towards H2PO2− shown in Fig. S10, similar quenching effects were observed after adding
4
the same amount of NaH2PO4/Na2HPO4 to the L-Zn2+ solution.
Considering that Zn2+ ions usually coordinated with N2O2 cavities of The fluorescence titration experiment of sensor L-Zn2+ (5.0 × 10− 5
bis(salamo)-like compound H3L [37–40], it caused the suppression of M) to HPO2− 4 ions was performed as shown in Fig. S11. When titrated to

the PET (photoinduced electron transfer) effect of the compound H3L 0.88 equiv., the fluorescence intensity of the solution is no longer
and a significant enhancement of fluorescence [29]. Attempts were change. In addition, the minimum limit of detection (LOD) for the
made to add different anions to make the compound H3L release from identification could be calculated as 4.30 × 10− 8 M (Eq. S2). The linear
coordinated environment. fit of the minimum detection is shown in Fig. S12.
The fluorescence effects of various anions on the sensor L-Zn2+ were
investigated in DMF/H2O (9/1, v/v, pH = 7.4) system. As shown in 3.3. Time response of the fluorescence sensor
Fig. 4a, a very significant fluorescence quenching of the sensor L-
Zn2+(5.0 × 10− 5 M) was found after the addition of H2PO−4 (10 equiv.). The time response of fluorescent chemosensor L-Zn2+ to H2PO−4 an­
However, the fluorescence emission of L-Zn2+ is almost enhanced by the ions was further investigated. As shown in Fig. S13, the experimental
addition of other common anions such as (B4O2− 7 , Br , Cl , ClO4 , CN ,
− − − − results showed that the fluorescence intensity reaches stability after 50 s.
CO2−
3 , F −
, HCO −
3 , HS −
, HSO−
4 , NO−
2 , NO2−
3 , OAc−
, HCO −
3 , S2−
, S O
2 3
2−
, and The result indicated that the sensor L-Zn2+ can rapidly identify
SCN− anions). In addition, the fluorescence selectivity of the sensor L- H2PO−4 anions.
Zn2+ (5.0 × 10− 5 M) for H2PO−4 was investigated by competition ex­
periments relative to other common anions (5.0 × 10− 4 M) in Fig. 4b. 3.4. Mechanism speculation and demonstration
The experimental results showed that the fluorescence is completely
quenched by adding H2PO−4 (5.0 × 10− 4 M) to the solutions of different Bis(salamo)-like coumpunds are ideal ligands for many transition
anions one by one. The fluorescence titration experiment of the sensor L- metals. The oxime nitrogen atoms and the hydroxyl oxygen atoms of the
Zn2+ (5.0 × 10− 5 M) for H2PO−4 ions was investigated in DMF/H2O (9/1, compound H3L have two coordination sites that can be coordinated with
v/v, pH = 7.4) solution as shown in Fig. 4c. When 0.01 equivalents of Zn2+ ions [41–45]. Usually, the Zn2+ ions covalently bridging the C=N
H2PO−4 ions were added dropwise, a slight blue shift occurred, and the group of salamo-like compounds exhibit fluorescence due to the sup­
color of the solution gradually changed from bright green to blue-cyan pression of the C=N isomerization of the excited state [28]. As shown in
when it was continuously increased to 0.87 equivalents. This is consis­ Fig. 5, in the chelation enhanced fluorescence (CHEF) effect, the lone
tent with the color of the compound H3L, which may also reflect the pair electrons on the oxime nitrogen atoms are involved in bonding with
combination of H2PO−4 ions with Zn2+ ions, allowing the release of H3L. Zn2+ions so that the energy of the lone pair drops below the energy of
Also, the minimum limit of detection (LOD) for identification can be the ground state of the fluorophore (aromatic ring) and therefore cannot

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L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

Fig. 4. (a) Fluorescence intensity plots generated by adding various anions to the solution containing the sensor L-Zn2+ in DMF/H2O (9/1, v/v, pH=7.4) system
(Insets: fluorescence color of L-Zn2+ with and without H2PO−4 under a 365 nm UV lamp); (b) Column chart of fluorescence intensity of various interfering anions
added to the sensor L-Zn2+ solution containing H2PO−4 . From 1 to 19: L-Zn2+, H2PO−4 B4O2− − 2− − − − − − 2−
7 , Br , Cl , ClO4 , CN , CO3 , F , HCO3 , HS , HSO4 , NO2 , NO3 , OAc ,
− − − −

HCO−3 , S2− , S2O2−

3 , SCN −
anions; (c) Fluorescence spectra of sensor L-Zn 2+
with increasing H 2PO −
4 concentrations; (d) Fluorescence intensity plots of the sensor L-Zn 2+

with H2PO−4 anions at different pH conditions (λex= 372 nm).

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L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

Fig. 5. The relative energy distribution of orbitals of the compound H3L in (a) Fluorescence restored by the CHEF effect and (b) Fluorescence quenched by the
PET effect.

Fig. 6. (a) HOMO-LUMO energy of the compound H3L and sensor L-Zn2+; (b) UV–Vis spectra of H3L (1.0 × 10− 5
M), adding Zn2+ ions (2.0 × 10− 5
M) and adding
Zn2++H2PO−4 ions (2.0 × 10− 5 M) in DMF/H2O solution (9/1, v/v, pH = 7.4).

provide electrons to the excited state of the aromatic ring [46]. Zn2+ ions charge transfer will occur [51–55]. It is evidence that the coordination
electrostatically attract electrons, thereby increasing the oxidation po­ of Zn2+ ions change the internal charge transfer (ICT) process, forcing
tential of the analyte-bound receptor so that the thermodynamics of PET PET effect to be suppressed and fluorescence to be turned on [56,57].
is no longer favorable, thus restoring fluorescence [47]. However, the As shown in Fig. 6b, with the addition of Zn2+ ions to the H3L so­
fluorescence intensity of the compound H3L is very weak, which lution, there are new absorption peaks in the 325–450 nm range. This
attributed to the effect of PET. Specifically, the quenching orbital (lone indicated that Zn2+ ions have coordinated with H3L [58–61]. Surpris­
pairs of oxime nitrogen atoms) has higher energy than the HOMO of ingly, when H2PO−4 ions were added to H3L solution containing Zn2+
fluorophores. When an electron is excited from the HOMO to the excited ions, the absorption peaks of the system are very similar to the ab­
state of the fluorophore, an electron from the lone pair falls into the gap sorption peaks of H3L. It is strongly confirmed that the quenching effect
of the fluorophore HOMO, preventing the excited electron from falling of sensor L-Zn2+ to H2PO−4 ions is caused by the mechanism of the ligand
back to the ground state and thus quenching the fluorescence [48]. replacement [62–66]. The possible detection mechanism is shown in
As shown in Fig. 6a, the lone pair of electrons on the oxime nitrogen Scheme 2.
atoms is transferred to the benzene rings of the salicylaldehyde in the
excited state [49,50]. When H3L coordinated to Zn2+ ions, ligand-metal

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L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

Fig. 7. Fluorescence changes of H3L-based paper strips after adding Zn2+ and H2PO−4 under 365 nm of UV lighting.

Scheme 1. Synthetic route to the compound H3L.

Scheme 2. Possible recognition mechanism.

3.5. Application study In addition, various H2PO−4 concentrations were added to distilled
water, tap water and Yellow River water samples by the standard
Fluorescent detection paper strips are made by immersing the filter addition method. By testing the fluorescence intensity change of sensor
paper in the solution of the compound H3L (5 × 10− 5 M) and then drying 2+
L-Zn , the concentration of H2PO4 ions in different water samples was
−

it in air. As shown in Fig. 7, the color of the paper strips changes from obtained. As shown in Table 2, the experimental result confirmed that
pale blue to green to deep blue by the addition of Zn2+ and H2PO−4 ions sensor L-Zn2+ has good detection capability in the real enviroment.
under 365 nm UV light. Thus, the paper strips can simply detect H2PO−4
ions in solution.

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L.-C. Feng et al. Journal of Molecular Structure 1289 (2023) 135941

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No data was used for the research described in the article. [18] W.T. Guo, T.X. Ji, Y.H. Deng, J. Liu, Y.T. Gou, Facile synthesis of a
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Acknowledgment [19] J.Q. Zhang, G.X. Yao, Y.J. Yan, L. Xu, Y. Zhang, Structurally characterized salamo-
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This work was supported by the Science and Technology Program of molstruc.2022.132772.
Gansu Province (Grant No. 21YF5GA057) and the Basic Research Top [20] L.L. Man, L. Tong, L.L. Gan, R.Y. Li, H.R. Mu, A N2O2-tetradentate dioxime
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