A Pyrene-based Probe for Antimony with Special Excimer Fluorescence

Article abstract of DOI:10.1002/zaac.202000195

Py-IPH, a pyrene-based fluorogen with good thermal and mechanical stability was simply prepared by the Schiff base reaction and applied in the detection of antimony. Py-IPH presented special excimer fluorescence in the mixture of THF and water with 80 per

Full text of DOI:10.1002/zaac.202000195

Journal of Inorganic and General Chemistry
DOI: 10.1002/zaac.202000195
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
A Pyrene-based Probe for Antimony with Special Excimer
Fluorescence
Yijia Wang,[a] Yuansong Huang,[a] Lili Wang,[a] Huagang Ni,[a] Zhihai Cao,[a] and Minghua Wu*[a]
Abstract. Py-IPH, a pyrene-based fluorogen with good thermal and
mechanism was demonstrated to be the increasing speed of the forma-
mechanical stability was simply prepared by the Schiff base reaction tion of pyrene excimers in the system owing to the coordination be-
and applied in the detection of antimony. Py-IPH presented special
excimer fluorescence in the mixture of THF and water with 80% of
tween antimony and IPH group in Py-IPH. Moreover, based on the
special interaction between Py-IPH and antimony, it could distinguish
water, and exhibited perfect fluorescent response to antimony. The antimony with other cations well with high specificity and selectivity.
in the measurement of antimony. For example, Mahmoud’s and
Yu’s groups prepared nanowires with core-shell structure and
quantum dots composed of bovine serum albumin (BSA)/CdTe
for the detection of antimony, respectively, but the preparation
for the materials were a little difficult.[19,22] In our previous
work, a simple chem-sensor for antimony, TPE-IPH, was de-
Introduction
Antimony is one kind of widely used catalysts in the poly-
ester industry[1] and also has been frequently applied in the
fields such as pharmaceutical products, glass fire retardants,
dyestuffs and semiconductors.[2,3] However, during the produc-
ing process of polyester fibers, the used antimony compounds
signed based on aggregation induced emission, but its fluores-
will be pulled out with the dyeing and printing wastewater, and
cent response to antimony was not high enough,[26] which
influence the environment around the companies seriously.[4,5]
should be improved by the exploration of other kind of
Antimony is a kind of toxic compound, which will do seri-
ous harm to the health of human beings as well as the plants
fluorogens based on different mechanism.
Pyrene is a common used dye with planar conjugate struc-
in the world, and cause the diseases such as hepatocirrhosis
ture and special excimer fluorescent property.[27] When the
and cancer.[6,7] It has been regarded as priority pollutant by the
concentration of pyrene solution was high, the excited pyrene
United States Environmental Protection Agency (USEPA) and
fluorogens will pack with each other and emit fluorescence at
European Union (EU),[8,9] and the upper limit of antimony in
about 460 nm, which is referred to the pyrene excimers. Sim-
textile dyeing and finishing industry water pollutant is stipu-
lated as 0.1 mg·L–1 by the Chinese government. So it is of
ilar phenomenon can be observed when pyrene-based com-
pound is added in the mixture of its solvent and non-solvent
significant importance to explore efficient way for the treat-
with suitable fraction, which can force the aggregation of com-
ment of antimony pollution, and the detection of antimony
pounds and give a hand to the formation of pyrene exci-
mers.[28,29] The formation of pyrene excimers will be influ-
enced by lots of factors, such as the concentration of pyrene
molecules in the system, the interaction between the pyrene
fluorogens, the steric configuration of the pyrene-based mol-
ecules and so on.[30,31] Lots of pyrene-based fluorescent probes
have been reported to be used in the response to heavy metals,
temperature and so on based on their excimer fluorescent prop-
erty,[32,33] so it maybe a feasible way for combining antimony
reactive functional group with pyrene core to design pyrene-
concentration in the wastewater is indispensable.
Nowadays, lots of methods have been reported to be applied
in the detection of antimony, such as atomic fluorescence spec-
trometry,[10,11] inductively coupled plasma mass spectrometry
(ICP-MS),[12,13] hydride generation atomic fluorescence spec-
trometry[14,15] and atomic absorption spectrometry.[16,17] How-
ever, the instruments are always with high cost and energy
consumption, and the preparation of the materials need com-
plex steps and long time, so new way should be found for
simple and convenient detection of antimony. Fluorescent
probes are useful tools for the detection of chemicals because basd antimony probes, which can change the speed for the
of its sensitive response to the determinants by fluores-
cence.[18] Till now, different kinds of fluorescent materials,
such as fluorescent molecules/nano-materials,[19,20] quantum
dots[21,22] and metal-organic frameworks[23–25] have been
widely applied in the field of bio-/chemical detection, and also
formation of pyrene excimers in the system, and achieve the
fluorescent detection of antimony with high sensitivity.
As reported in our previous work and other references, func-
tional groups with N/O atoms can coordinate with antimony
specifically and have been used in the design of antimony
probes frequently.[19,22,26] In this work, a simple N/O contain-
ing molecule, 2-aminophenol, is linked to the pyrene core by
the mild Schiff base reaction to prepare antimony chem-sensor,
Py-IPH. The thermal and mechanical stability of Py-IPH will
be tested, the excimer fluorescent property of Py-IPH will be
* Dr. M. Wu
E-Mail: wmh@zstu.edu.cn
[a] Key Laboratory of Advanced Textile Materials and Manufacturing
Technology
Zhejiang Sci-Tech University
Hangzhou, 310018, P. R. China
Z. Anorg. Allg. Chem. 0000, ᭿,0–0
1
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
demonstrated, and its fluorescent response to antimony as well fluorescence at around 549 nm as prepared. The emission
as the mechanism will be explored. We hope to find it as a wavelength slightly blue-shifted to 543 nm after being ground
simple and convenient way for antimony detection with high hardly and it shifted back to 545 nm when fumed by the DCM
sensitivity, specificity, and selectivity, and can be used in the vapor. It could be found that the change of the maximum fluo-
treatment of antimony in dyeing and printing wastewater in the rescent wavelength of Py-IPH was only about 5 nm under a
future.
series of treatment, indicating its perfect mechanical stability.
Results and Discussion
The synthetic route of Py-IPH and its nuclear magnetic reso-
nance (NMR) spectra are shown in Figure 1. It could be found
that Py-IPH was simply prepared by the mild Schiff base reac-
tion between the aldehyde group in pyrene fluorogen and the
amino group in 2-aminophenol. The peaks at around 9.60 ppm
1
in H NMR spectrum and 155.084 ppm in 13C NMR spectrum
were both referred to the hydrogen atom in the double bond
of Py-IPH, which demonstrated the successful preparation of
the target probe.
Figure 3. (A) UV spectrum of Py-IPH in THF and (B) the fluorescent
spectra of Py-IPH solids under different treatment. λex: 400 nm, con-
centration of Py-IPH solution: 10 μM.
Fluorescent Property
Pyrene was demonstrated with special excimer fluorescent
property and had been widely used for chem-detection in re-
ported works.[32,33] In order to achieve the detection of anti-
mony by fluorescence, we first tested the fluorescent property
of Py-IPH in the mixture of THF and water, and explored its
emission under different states. Herein, THF was the good sol-
vent of Py-IPH and water was the non-solvent, which was used
to impel the formation of excimers in the mixtures.
Figure 1. The synthetic route of Py-IPH and its 1H NMR (left) and
13C NMR (right) spectra in d-CDCl3.
The fluorescent spectra of the mixtures with different water
fraction were given in Figure 4. As shown in Figure 4A, Py-
IPH was almost no emission in dilute THF solution when ex-
cited by 400 nm, and the fluorescence increased quite slightly
when the water fraction was lower than 60%. The fluorescent
intensity of the mixture enhanced significantly when the per-
centage of water was up to 70%, and then reached the highest
with maximum wavelength at 478 nm when 80% of water was
containing in the mixture. The boosted emission of the mixture
Then we tested the thermal stability of Py-IPH by the ther-
mogravimetric analysis (TGA) and differential scanning calo-
rimetry (DSC). As shown in Figure 2, Py-IPH would not de-
compose until the temperature reached 280 °C, and its melting
temperature (Tm) was higher than 160 °C, regarding it as a
fluorescent probe with high thermal stability.
Figure 2. (A) TGA thermogram of Py-IPH, recorded after pre-
warming at 120 °C for 10 min under nitrogen at a heating rate of
10 K·min–1. (B) DSC graph of Py-IPH, atmosphere: N2; heating rate:
10 K·min–1.
Figure 4. (A) FL spectra of Py-IPH in the THF/water mixtures with
different water fraction. (B) Plot of FL intensity of Py-IPH in different
THF/water mixtures with different water fraction. Insert: photos of
Py-IPH in the THF/water mixture with 80% of water taken under day-
The mechanochromic property of Py-IPH was also studied.
As shown in Figure 3, the maximum adsorption wavelength of
Py-IPH was located at 400 nm, and it emitted yellow-green light and UV light. λex: 400 nm, concentration of Py-IPH: 200 μM.
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
2
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
Figure 5. FL intensity of the mixture of Py-IPH and SbIII in the THF/water mixture under different conditions. λex: 400 nm, concentration of
SbIII: 0.1 mg·mL–1.
could be owed to the formation of Py-IPH excimers with suit- As shown in the insert image of Figure 6B, when 0.1 mg/mL
able percentage of non-solvent in the system, which would of antimony was added into 200 μM of Py-IPH, the yellow
force the formation of Py-IPH excimers. When the water frac- solution of Py-IPH changed to clear and colorless, meanwhile
tion of the mixture reached 90%, the fluorescence of the mix- the blue-green emission referred to the excimers formed by
ture was hardly quenched with red-shift of the maximum pyrene fluorogens enhanced evidently. Both of the phenomena
wavelength, which could be explained by π–π stacking of the demonstrated that Py-IPH exhibited perfect enhanced fluores-
pyrene fluorogens owing to their plane configuration. The cent response to low concentration of antimony.
photographs of Py-IPH in the mixture with 80% of water taken
under daylight and UV lamp were given in the insert image of
Figure 4B. It showed that Py-IPH was a bright yellow turbid
solution with strong blue-green emission, which indicating the
existence of Py-IPH excimers in the mixture.
Antimony Detection
The fluorescent response of Py-IPH to antimony was taken
in the mixture of THF and water, and the detective condition
was first studied. As shown in Figure 5, with same concentra-
Figure 6. (A) FL spectra and (B) I / I0–1 of Py-IPH in the mixture of
THF/water = 2/8 by volume with different concentration of SbIII. In-
sert: photos taken under daylight and UV light of Py-IPH with and
without 0.1 mg·mL–1 of SbIII in the THF/water mixture with 80% of
water. λex: 400 nm, concentration of SbIII: 0–0.5 mg·mL–1; concentra-
tion of Py-IPH: 200 μM.
tion of antimony in the system, the concentration of Py-IPH,
the equilibration time for the samples, as well as the water
fraction of the mixture, would all influence the fluorescent in-
tensity of the mixtures with and without antimony. According
to the results shown in Figure 5, 200 μM of Py-IPH would be
used in the detection of antimony in the mixture of THF and
water with 80 percent of water, and the fluorescent measure-
ment of the samples would be taken after equilibration for
4 min in future experiments.
Mechanism
The fluorescent spectra of Py-IPH with different concentra-
Pyrene was reported with special excimer fluorescence in
tion of antimony were given in Figure 6. As shown in Fig- the mixture with suitable fraction of non-solvent, and the fluo-
ure 6A, Py-IPH itself emitted fluorescence with maximum rescent intensity was related to the concentration of the exci-
wavelength at about 480 nm in the mixture with 80% of water. mers formed in the system.[30] So in our system, the change of
With the increasing of the antimony concentration, the emis- the emission of the mixtures with and without antimony could
sion of the mixtures increased gradually with the blue-shift of be explained by the different speed for the increasing concen-
maximum fluorescent wavelength. When the concentration of tration of pyrene excimers in the mixture during the antimony
antimony reached 0.1 mg/mL, the fluorescent intensity of the detection process.
mixture reached the highest with maximum wavelength at
In order to explore the influence of antimony to the forma-
458 nm, indicating Py-IPH as a perfect probe for antimony. tion of pyrene excimers of Py-IPH, the change of the fluores-
The change of the maximum fluorescence of the mixtures with cent spectra for Py-IPH as well as the mixture of Py-IPH and
the increasing concentration of antimony was clearly shown in antimony with time were recorded (Figure 7). As shown in
Figure 6B, it could be found that the highest enhancement of Figure 7A, once 200 μM of Py-IPH was added in the mixture
the mixture was up to 11.32 folds and the detection limit of with 80% of water, it emitted quite weak fluorescence at about
antimony was calculated to be about 0.16 mg·L–1. The photo- 480 nm, because small amount of pyrene excimers could be
graphs of the mixtures with and without antimony under day- formed at that time. Then the fluorescent intensity of the mix-
light and UV lamp were also recorded by the digital camera. ture increased and the maximum fluorescent wavelength blue-
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
3
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
shifted to 472 nm gradually, indicating the formation of the Figure 5B). What’s more, the formation of pyrene excimers
pyrene excimers with time, and resulting in the dense pyrene was also related to the ratio of solvent/non-solvent in the sys-
excimer concentration in the mixture.
tem, which could influence the aggregated level of the pyrene
fluorogens. As shown in Figure 5C, with relatively low water
fraction (fW = 70%), the aggregation of pyrene moieties with
each other was not tightly enough, so it was not that easy for
antimony to speed up the formation of their excimers. Mean-
while, in the system with high water fraction such as 85% and
90%, the aggregation of pyrene fluorogens was so tightly that
it was hard for antimony to coordinate with the IPH groups in
Py-IPH molecules and switch the fluorescent intensity of the
mixtures. All of the results indicated that the fluorescent re-
sponse of Py-IPH to antimony was owing to the increasing
speed for the formation of pyrene excimers in the system,
which was caused by the coordination between the N and O
Figure 7. Change of the FL spectra of mixtures containing Py-IPH and
different concentration of SbIII with time in the mixture of THF/water atoms in IPH group of Py-IPH and antimony.
= 2/8 by volume. λex: 400 nm, concentration of Py-IPH: 200 μM, con-
centration of SbIII: (A) 0 mg·mL–1, (B) 0.1 mg·mL–1.
Specificity and Selectivity
For the mixture containing both 200 μM of Py-IPH and
0.1 mg·mL–1 of antimony, similar phenomenon could be ob-
served (Figure 7B), but the maximum fluorescent intensity of
the mixture was much higher than the mixture without anti-
mony at the same time, and the emission wavelength blue-
shifted to 459 nm, 13 nm more than Py-IPH itself (472 nm in
Figure 7A). These results could be explained by the interaction
between antimony and Py-IPH. As reported in our previous
work, antimony could coordinate with the N and O atoms in
IPH group of Py-IPH, force the Py-IPH molecules to close
with each other, increase the speed for the formation of pyrene
excimers, and then enhance the concentration of pyrene exci-
mers in the mixture much more efficiently then Py-IPH itself.
Thus, difference on fluorescent intensity of the mixtures with
and without antimony could be found evidently. The higher
concentration of the added antimony, the faster formation of
pyrene excimers, and the more folds for the increasing of the
emission of mixtures.
The mechanism supposed above could also be demonstrated
by the influence of Py-IPH concentration, water fraction of the
mixture, and equilibration time for samples on the fluorescent
response to antimony by Py-IPH. As shown in Figure 5A,
when the concentration of Py-IPH was 150 μM, the increasing
of the fluorescent intensity was a little smaller than the mixture
with 200 μM of Py-IPH, which could be owed to the relatively
low concentration of Py-IPH fluorogens for the formation of
pyrene excimers. When the concentration of Py-IPH was
higher, such as 300 μM and 500 μM, the pyrene fluorogens in
the mixture was high enough to pack with each other close, so
it would be a little hard for antimony to insert among them
and increase the speed of pyrene excimers formation, and the
enhancement of the emission of mixtures was not that large
comparing with the sample containing 200 μM of Py-IPH.
Similar reason could be used to explain the influence by
equilibration time. When the equilibration time was short, the
influence of antimony was inconspicuous, and when the equili-
bration time was as long as 22 min, both of the samples with
and without antimony could form pyrene excimers well, so the
In order to explore the specificity of antimony detection by
Py-IPH, different kinds of cations were used in the detection
system. As shown in the red bars in Figure 8, Py-IPH pre-
sented almost no fluorescent response to KI, CaII, NaI and CdII,
and only slight increasing of emission could be observed in
the mixtures containing MgII, PbII and ZnII. Meanwhile, HgII
as well as AlIII could have some interaction with Py-IPH and
caused the increase of fluorescence. However, these two cat-
ions could be easily distinguished with antimony by naked
eyes. As shown in the insert image of Figure 8, Py-IPH itself
was a bright yellow solution in the mixture of THF and water
with 80% of water, then the solution changed to transparent
colorless with the addition of antimony. As to the mixtures
containing AlIII and HgII, the color of the mixtures were light
yellow and light brown, respectively, which were quite dif-
ferent from that of antimony. The different response of Py-IPH
to antimony, AlIII and HgII should be owed to the different
coordinate level of the cations with Py-IPH. Antimony usually
existed as aqua compound under natural conditions, which me-
ant that the interaction between antimony and Py-IPH was rel-
Figure 8. FL response of Py-IPH to different kinds of cations (red)
and Py-IPH to SbIII in the present of different kinds of cations (blue)
in the mixture of THF/water = 2/8 by volume. Insert: photos taken
under daylight of Py-IPH and it with 0.1 mg·mL–1 of SbIII, AlIII, HgII
in the THF/water mixture with 80% of water. λex: 400 nm, concentra-
difference of the fluorescent intensity was not that clear (see tion of Py-IPH: 200 μM, concentration of cations: 0.1 mg·mL–1.
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
4
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
(d, 1 H), 8.80–8.73 (d, 1 H), 8.30–8.15 (m, 5 H), 8.14–8.02 (m, 2 H),
atively weak, so it could increase the speed of the formation
7.55–7.45 (d, 1 H), 7.35–7.25 (m, 1 H), 7.18–7.10 (d, 1 H), 7.09–7.00
(d, 1 H). 13C NMR (100 MHz, CDCl3): δ = 155.084, 152.486,
136.613, 133.516, 131.150, 130.571, 130.374, 129.087, 128.975,
128.917, 127.863, 127.347, 126.257, 126.229, 125.979, 125.849,
124.906, 124.698, 124.442, 121.598, 120.251, 116.023, 115.134 ppm.
of pyrene excimers and boost the emission of the mixtures.
But as to AlIII and HgII, the interaction would be a little
stronger, which might increase the fluorescence of pyrene exci-
mers, but also quench it by the π–π stacking of the pyrene
fluorogens. All the results suggested that Py-IPH could distin-
guish antimony with other commonly used cations well.
The influence of these cations on the detection of antimony Acknowledgements
by Py-IPH was also tested. As shown in the blue bars of Fig-
ure 8, with the addition of 0.1 mg·mL–1 of antimony, the fluo-
rescence of Py-IPH increased 10.32 folds. When other cations
were then added, little impact on the emission of the mixtures
could be found, which demonstrated that Py-IPH was a fluo-
rescent probe for antimony with good selectivity and specific-
ity.
This work was supported by the Key Laboratory of Advanced Textile
Materials and Manufacturing Technology (Zhejiang Sci-Tech Univer-
sity) and the Fundamental Research Funds of Zhejiang Sci-Tech Uni-
versity (Grant No. 17012145-Y).
Keywords: Antimony detection; Selectivity; Specificity;
Pyrene-based fluorescent probe; Excimer emission
Conclusions
In conclusion, Py-IPH, a molecule with special excimer
fluorescence, was prepared for antimony detection. The probe
References
could be synthesized by simple Schiff base reaction and pres- [1] J. O. Vinhal, A. D. Gonçalves, G. F. B. Cruz, R. J. Cassella, Tal-
anta 2015, 150, 539–545.
[2] K. E. Toghil, M. Lu, R. G. Compton, Int. J. Electrochem. Sci.
2011, 6, 3057–3076.
[3] P. Smichowski, Talanta 2008, 75, 2–14.
ent good thermal and mechanical stability. In the mixture with
THF and water, Py-IPH exhibited strong excimer fluorescence
when the water fraction was 80%, and the fluorescent intensity
increased gradually with the addition of antimony. When the
concentration of antimony was up to 0.1 mg·mL–1, the emis-
sion of the mixture reached the highest with I / I0 value as
11.32. Based on the special excimer optical property of the
pyrene-based probe as well as the coordination between anti-
[4] F. A. E. Toufaili, G. Feix, K. H. Reichert, J. Polym. Sci. Part A:
Polym. Chem. 2006, 44, 1049–1059.
[5] M. Filella, N. Belzile, Y. W. Chen, Earth-Science Rev. 2002, 57,
125–176.
[6] A. Samadi-Maybodi, V. Rezaei, Microchim. Acta 2012, 178, 399–
404.
mony and the IPH group of Py-IPH, the fluorescent response [7] M. Hashemzaei, J. Pourahmad, F. Safaeinejad, K. Tabrizian, F.
Akbari, G. Bagheri, Toxicological Environ. Chem. 2015, 97, 256–
265.
speed for the formation of pyrene excimers in the system.
[8] S. Keresztes, E. Tatár, V. G. Mihucz, I. Virág, C. Majdik, G.
of Py-IPH to antimony was demonstrated to be the increasing
What’s more, Py-IPH could distinguish antimony with other
commonly used cations well with good specificity and selec-
tivity owing to its special interaction with antimony.
Záray, Sci. Total Environ. 2009, 407, 4731–4735.
[9] L. AlSioufi, A. M. S. Campa, D. Sánchez-Rodas, Microchemical
J. 2016, 124, 256–260.
[10] G. S. Santos, L. O. B. Silva, A. F. S. Júnior, E. G. P. Silvac,
W. N. L. Santos, J. Brazilian Chem. Soc. 2018, 29, 185–190.
[11] M. C. Cardozo, D. D. Cavalcante, D. L. F. Silva, W. N. L. Santos,
M. A. Bezerra, Anais Academia Brasileira Ciencias 2016, 88,
1179–1190.
Experimental Section
Materials: Pyrene-1-carbaldehyde, 2-aminophenol, and chromato-
graphic pure THF were purchased from J&K, other reagents such as
methanol and ethanol were purchased from Sinopharm Chemical Rea-
gent Co., Ltd. All the chemicals were used without further purification.
[12] M. C. Saha, Atomic Spectrosc. Norwalk Connecticut 2017, 38, 7–
11.
[13] X. Liu, Z. Zhu, Z. Bao, D. He, H. Zheng, Z. Liu, S. Hu, Anal.
Chem. 2019, 91, 928–934.
[14] L. Chen, Z. Lei, K. Hu, S. Yang, X. Wen, Microchemical J. 2018,
141, 215–219.
[15] H. Wu, X. Wang, B. Liu, Y. Li, S. Lu, J. Tian, J. Zhao, W. Yang,
Z. Yang, Spectrochim. Acta Part B, Atomic Spectrosc. 2011, 66,
74–80.
Instruments: 1H and 13C NMR spectra were measured with a Mercury
plus 300 MHz NMR spectrometer in d-CDCl3 with tetramethyl-silane
(TMS; δ = 0 ppm) as internal standard. UV/Vis absorption spectra were
carried out on UV-5500PC ultraviolet and visible spectro-photometer
(Shanghai Metash Instruments Co., Ltd.). Fluorescence (FL) spectra
were recorded on a spectro-fluorophotometer (RF-5301PC, SHIM-
ADZU, Japan).
[16] J. K. Andrade, C. K. Andrade, M. L. Felsner, S. Percio, V. E.
Anjos, Microchemical J. 2017, 133, 222–230.
˙
[17] T. Unutkan, I. Koyuncu, C. Diker, M. Fırat, Ç. Büyükpınar, S.
Bakırdere, Bull. Environ. Contamination Toxicology 2019, 102,
122–127.
Synthesis of (E)-2-((Pyren-1-ylmethylene)amino)phenol (Py-IPH):
Py-CHO (1.00 g, 4.34 mmol) and 2-aminophenol (0.52 g, 4.78 mmol)
were dissolved in 50 mL of the mixture of methanol and ethanol (v:v
= 1:1) and the resulting solution was stirred at room temperature for
12 h until the appearance of yellow solid and then refluxed for another
12 h. The precipitate was filtered at room temperature, washed with
iced ethanol, and dried to yield Py-IPH as a bright yellow solid in
63% yield. 1H NMR (400 MHz, CDCl3): δ = 9.60 (s, 1 H), 8.88–8.80
[18] T. Gao, L. Zhao, L. Gao, J. Zhang, L. Zhai, X. Niu, T. Hu, Z.
Anorg. Allg. Chem. 2019, 645, 934–939.
[19] S. Ge, C. Zhang, Y. Zhu, J. Yu, S. Zhang, Analyst 2010, 135,
111–115.
[20] A. Burns, H. Ow, U. Wiesner, Chem. Soc. Rev. 2006, 35, 1028–
1042.
[21] I. L. Medintz, H. T. Uyeda, E. R. Goldman, H. Mattoussi, Nat.
Mater. 2005, 4, 435–446.
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
5
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
[22] W. E. Mahmoud, Sensors Actuators B: Chem. 2017, 238, 1001– [29] M. H. Nguyen, T. T. H. Khuat, H. H. Nguyen, T. H. Dinh, Z.
1007.
Anorg. Allg. Chem. 2019, 645, 113–119.
[23] W. X. Lin, J. Q. Gong, L. Q. Fang, K. Jiang, Z. Anorg. Allg.
Chem. 2019, 645, 1161–1164.
[24] X. Duan, R. Lv, S. Li, J. Tang, J. Ge, D. Zhao, Z. Anorg. Allg.
Chem. 2019, 645, 955–959.
[25] D. Yue, Y. Wang, D. Chen, Z. Wang, Chem. Commun. 2020, 56,
4320–4323.
[26] Y. Huang, J. Lin, L. Wang, Z. Cao, Y. Wang, M. Wu, Z. Anorg.
Allg. Chem. 2020, 646, 47–52.
[30] S. A. McNelles, J. L. Thoma, A. Adronov, J. Duhamel, Macro-
molecules 2018, 51, 1586–1590.
[31] T. Takaya, T. Oda, Y. Shibazaki, Y. Hayashi, H. Shimomoto, E.
Ihara, Y. Ishibashi, T. Asahi, K. Iwata, Macromolecules 2018, 51,
5430–5439.
[32] R. Kumar, R. Bawa, P. Gahlyan, M. Dalela, K. Jindal, P. K. Jha,
M. Tomar, V. Gupta, Dyes Pigm. 2019, 161, 162–171.
[33] X. Y. Zeng, R. Liu, D. D. Liu, Q. Y. Liu, Y. L. Wang, Z. Anorg.
Allg. Chem. 2019, 645, 1379–1383.
[27] X. Feng, J. Hu, C. Redshaw, T. Yamato, Chem. Eur. J. 2016, 22,
11898–11916.
[28] F. G. A. Lister, N. Eccles, S. J. Pike, R. A. Brown, G. F. S. White-
head, J. Raftery, S. J. Webb, J. Clayden, Chem. Sci. 2018, 33,
6860–6870.
Received: May 3, 2020
Published Online: ᭿
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
6
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
Y. Wang, Y. Huang, L. Wang, H. Ni, Z. Cao, M. Wu* ..... 1–7
A Pyrene-based Probe for Antimony with Special Excimer
Fluorescence
Z. Anorg. Allg. Chem. 0000, 0–0
www.zaac.wiley-vch.de
7
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim