A water soluble naphthalimide-based chemosensor for fluorescent detection CN? in pure water and its application in practical samples

Article abstract of DOI:10.21577/0103-5053.20180030

By rationally introducing aromatic carboxyl functionalized 1,8-naphthalimide, a water soluble fluorescent chemosensor (DA) was successfully synthesized. It could selectively and sensitively detect CN? in pure water via an intramolecular charge transfer to

Full text of DOI:10.21577/0103-5053.20180030

http://dx.doi.org/10.21577/0103-5053.20180030
J. Braz. Chem. Soc., Vol. 29, No. 7, 1563-1569, 2018
Article
Printed in Brazil - ©2018 Sociedade Brasileira de Química
A Water Soluble Naphthalimide-Based Chemosensor for Fluorescent Detection CN−
in Pure Water and Its Application in Practical Samples
a,b
a
a
a
a
a
Li Wang, Wen-Ting Li, Wen-Juan Qu, Yan-Qing Fan, Hong Yao, Qi Lin,
a
,a
Tai-Bao Wei and You-Ming Zhang*
a
College of Chemistry and Chemical Engineering, Northwest Normal University,
30070 Lanzhou, Gansu, P. R. China
7
b
School of Chemical and Biological Engineering, Lanzhou Jiaotong University,
30070 Lanzhou, China
7
By rationally introducing aromatic carboxyl functionalized 1,8-naphthalimide, a water soluble
fluorescent chemosensor (DA) was successfully synthesized. It could selectively and sensitively
−
detect CN in pure water via an intramolecular charge transfer to twisted intramolecular charge
−
transfer (ICT-TICT) state change mechanism. The detection limit of the chemosensor DA to CN
−8
-1
-1
was 1.38 × 10 mol L which was lower than 1.9 μmol L (set by the World Health Organization
WHO)). Notably, DA displayed rapid response (about 1 s) for recognizing CN in pure water.
Furthermore, DA could be applied to monitoring CN in tap water. Meanwhile, we prepared the
−
(
−
−
test strips based on DA, which could rapidly and efficiently detect CN in water.
Keywords: water-soluble chemosensor, fluorescent, 1,8-naphthalimide derivative, CN−
recognition
Introduction
use of organic solvents usually damages the normal function
of biomolecules, thus, good water solubility are essential for
−
7
Cyanide (CN ) salts are extensively used in industry,
such as electric plating, gold mining, plastic production,
and other areas. However, cyanide is greatly toxic to
mammals with even a small amount of this species, leading
to emesis, unconsciousness, and finally to death. Therefore,
practical use of the chemosensors in biochemical research.
8
Although some of them could work in pure water, they did
1
not display enough sensitivity for the maximum allowable
-1
−
level (1.9 μmol L ) of CN in drinking water. Thus, it is
highly challenging to develop new soluble fluorescent
2
−
cyanide concentrations in drinking water must be lower
chemosensors for sensing CN with high sensitivity and
-1 3
than 1.9 μmol L . In this regard, the reasonable design
and synthesis of effective sensors to selectively detect
cyanide anion at the environmental and biological levels
excellent selectivity in 100% water solutions.
1,8-Naphthalimide derivatives are an excellent
environmentally sensitive fluorophore compounds,
which is extensively applied to various fields of science
4
have received a lot of attention.
9
Fluorescence sensors for specific anions play a
fundamental role in medical, environmental and biological
applications, what is more, it is one of the best tools with
high sensitivity, rapid response and easy performance, much
interest has been focused on the design and synthesis of
and technology. As a consequence of their strong blue
fluorescence and good photostability, 1,8-naphthalimide
derivatives are often used for fluorescence sensors, switchers
10
and ion probes. However, the application of naphthalimide
sensors was limited due to poor solubility. We all know that
5
11
fluorescent chemosensors for anions.
carboxyl not only has a remarkable coordination ability,
To date, much effort has been drawn to develop the
fluorescent chemosensors for CN . However, most of them
but also has an excellent hydrophilicity.
−
With these considerations in mind and based on
1
2
worked properly in a high percentage of organic solvent
our research interest in ions recognition, we designed
and synthesized a novel, low-cost and water soluble
chemosensor (DA) for fluorescent detecting cyanide ions
by rationally introducing aromatic carboxyl functionalized
6
media for the detection of cyanide ions. As we know, the
*
e-mail: zhangnwnu@126.com

–
1
564
A Water Soluble Naphthalimide-Based Chemosensor for Fluorescent Detection CN in Pure Water
J. Braz. Chem. Soc.
1
,8-naphthalimide. As expected, chemosensor DA
displays high sensitivity and rapid response (about 1 s)
−
for recognizing CN in pure water system. Compared with
most of the previously reported fluorescent chemosensors
−
13
for CN and naphthalimide sensors, the advantage of DA
is that it could work in 100% water solutions. It is worth
noting that compared with recently reported aromatic
carboxyl functionalized 1,8-naphthalimide chemosensors,
DA can be directly dissolved in pure water without
changing COOH into COONa.
Scheme 1. Synthetic procedures of chemosensor DA.
General procedure for fluorescence spectra experiments
-
1
Experimental
The stock solution of DA (0.2 mmol L ) in pure water
pH = 7.2) was prepared and stock at room temperature,
(
-
1
Materials and apparatus
which diluted to a concentration of 20 μmol L as the
determined solution. The aqueous solutions of anions
(10 mmol L ) (F , Cl , Br , I , AcO , SO , H PO , ClO ,
4 2 4 4
CN , SCN , S and OH ) were prepared via sodium salts.
The fluorescence spectra were obtained by excitation at
315 nm. The excitation and emission slit widths were
both 5 nm.
-1
−
−
−
−
−
−
−
−
Fresh double-distilled water was used throughout the
experiments. All other reagents and solvents (analytical
grade) were commercially available and were used without
−
−
2−
−
1
further purification. H nuclear magnetic resonance (NMR)
spectra was recorded on an Agilent DD2 at 600 MHz
1
spectra. H chemical shifts are reported in ppm downfield
1
from tetramethylsilane (TMS, δ scale with the solvent
resonances as internal standards). Fluorescence spectra
were recorded on a Shimadzu RF-5310 (Japan). Melting
points were determined on an X-4 digital melting-point
apparatus (Beijing Tech Instrument Co., Ltd., China) and
were uncorrected. Mass spectra (MS) were recorded on
a Bruker Esquire 3000 plus mass spectrometer (Bruker-
FranzenAnalytik GmbH, Bremen, Germany) equipped with
ESI (electrospray ionization) interface and ion trap analyzer.
General procedure for H NMR experiments
1
For H NMR titrations, sensor DA was prepared in
DMSO-d and NaCN was prepared in double-distilled
water. First of all, only sensor DA in DMSO-d was added
into the NMR tube, and then CN anion was added at 0.1,
0.5, 1.0, 2.0 and 4.0 equiv. sequentially. All solutions were
mixed directly in the NMR tube.
6
6
−
Practical samples analysis
Synthesis of the chemosensor DA
For practical sample analysis, the tested water tap
−
Compound DA was synthesized by condensation
reaction of anthranilic acid and 1,8-naphthalic anhydride
samples were prepared by adding known amounts of CN .
The fluorescence spectrum of each sample was tested
for three times, and the found concentration of CN was
1
4
−
(
1
Scheme 1). Anthranilic acid (0.55 g, 4.0 mmol) and
,8-naphthalic anhydride (0.79 g, 4.0 mmol) were dissolved
measured according to the developed calibration curve.
Preparation of the test strips
in absolute dimethylformamide (DMF, 20 mL) at 80 °C.
The reaction mixture was stirred and refluxed for 7 h. The
mixture was still clear liquid after cooling down to room
temperature. White precipitate appeared after adding
distilled water, through filtration, washed with ethanol and
dried under vacuum, then obtained the product DA in 85%
yield (mp > 300 °C).
Theteststripswerecarriedoutbysubmersingfilterpapers
in the pure water solution of DA (2.0 × 10 mol L ) and then
dried in air. The CN water solution (2.0 × 10 mol L ) and
competitive anions water solution were dropped on the test
strips. After drying, the images were recorded by a digital
camera under UV lamp.
−4
-1
−
−4
-1
Characterization data for DA
1
H NMR (600 MHz, DMSO-d ) d 12.85 (s, 1H, COOH),
6
8
2
1
.49 (m, 4H, Nap-H), 8.08 (m, 1H, Ph-H), 7.89 (t, J 6 Hz,
H, Nap-H), 7.75 (t, J 6 Hz, 1H, Ph-H), 7.60 (t, J 6.6 Hz,
Results and Discussion
H, Ph-H), 7.50 (d, J 6 Hz, 1H, Ph-H). ESI-MS m/z:
We researched the fluorescent response of chemosensor
DA to various anions in 100% water solutions, including
+
[M + Na] calcd. for C H NO Na: 340.06; found: 340.01.
19
11
4

Vol. 29, No. 7, 2018
Wang et al.
1565
−
−
−
−
−
−
−
−
−
−
2−
F , Cl , Br , I , AcO , SO , H PO , ClO , CN , SCN , S
4
2
4
4
−
and OH . As shown in Figure 1, the maximum fluorescent
emission band of free DA appeared at 390 nm. When
−
5
equivalents of CN was added to the pure water solution of
chemosensor DA, the fluorescence emission band at 390 nm
significantly reduced. The obvious color change from
bright blue to colorless could be distinguished by naked-
eyes through UV lamp (Figure 1). To further evaluate the
selectivity of chemosensor DA, the same experiments were
−
−
−
−
−
−
−
also conducted using F , Cl , Br , I , AcO , SO , H PO ,
4
2
4
−
−
2−
−
ClO , SCN , S and OH . Whether in the fluorescent
4
spectra or by naked-eyes through UV lamp, nearly no
obvious fluorescence responses were observed with
these anions (Figure 2), demonstrating DA has excellent
−
fluorescent selectivity toward CN in pure water.
-1
Figure 2. (a) Fluorescence spectra of DA (20 μmol L ) upon addition
of 5 equiv. of various anions in pure water media (λex = 315 nm);
(
b) fluorescence responses of DA in the presence of 5 equiv. of different
anions in pure water (λex = 315 nm).
decreased gradually and reached to minimum value
−
by 3.8 equiv. of CN (Figure 3a). The binding constant
value Ka, which was evaluated by the Benesi-Hildebrand
5
-1
method, was found to be 6.08 × 10 mol L (Figure 3b),
and pK = 4.17. Furthermore, the detection limit (LOD)
a
calculated according to the basis of 3σ/S (where σ is
the standard deviation of the blank solution and S is the
−
8
-1
slope of the calibration curve) was 1.38 × 10 mol L
-
1
Figure 1. Fluorescence spectra of DA (20 μmol L ) in pure water media
−
(Figure S3, Supplementary Information (SI) section), which
is superior to other cyanide chemosensors (Table 1) and far
below the World Health Organization (WHO) guideline of
in the presence of CN (5 equiv.) (λex = 315 nm). Inset: color change of
DA, DA + CN (5 equiv.) under UV lamp in pure water media.
−
Furthermore, the quantum yields of DA and DA + CN−
were calculated using the following equation 1:
1.9 μmol L .
-1 3
The pH effects were measured to investigate whether
the sensor is appropriate for the physiological detection
−
Yu = (Ys × Fu × As) / (Fs × Au)
(1)
(Figure 4). The detection of CN can operate well in the
pH range of 4.0-8.0 in pure water, which confirmed that
DA has also excellent sensing ability toward CN under
where Yu is the quantum yield of DA and DA + CN−;
Ys is the quantum yield of reference compound (quinine
sulfate, Ys = 0.55); Fu is the fluorescent integral of DA
−
physiological conditions.
−
We further examined the sensor’s reactivity toward CN
−
−5
-1
and DA + CN ; Fs is the fluorescent integral of reference
(Figure 5). While DA (2.0 × 10 mol L ) was treated with
−
−
compound;Au is the absorbance of DA and DA + CN ;As
CN (5 equiv.) in pure water, the fluorescence intensity at
is the absorbance of reference compound. The quantum
yield of DA and DA + CN were 0.4183 and 0.0594,
respectively.
390 nm decreased rapidly and reached a plateau in about
1 s. The kinetic test result proved that our sensor could
rapidly detect CN in pure water.
−
−
To get a quantitative idea of the sensing, the fluorescence
We further explore the selectivity of chemosensors DA
for cyanide when DA was treated with other competitive
titration experiment was further performed in pure water
−
−
−
−
−
−
−
−
−
(
Figure 3). Upon the addition of CN , the fluorescence
anions, such as F , Cl , Br , I , AcO , SO , H PO , ClO ,
4 2 4 4
−
2−
−
emission intensity of chemosensor DA at 390 nm
SCN , S and OH (Figure 6). The fluorescence emission

–
1
566
A Water Soluble Naphthalimide-Based Chemosensor for Fluorescent Detection CN in Pure Water
J. Braz. Chem. Soc.
Table 1. Sensors for cyanide determination
Sensor
Solvent
Quantum yield
Limit of detection / M
Reference
−
7
Bis(salamo)-type tetraoxime-based
Pyrene-benzothiazol-based
Naphthalene-based
Merocyanine-based
Indanedione-based
Phenazine-based
MeOH/H O = 1:1
–
0.23
–
8.91 × 10
15
16
17
18
19
20
21
22
23
2
−7
DMSO/H O = 1:1
2.8 × 10
2
−
7
6
7
6
H O
3.2 × 10
1.6 × 10
9.4 × 10
1.4 × 10
6.45 × 10
2
−
−
−
EtOH/H O = 9:1
–
2
THF/H O = 1:9
0.12
–
2
H O/DMSO = 7:3
2
−
8
Boronic-based
H O/CH CN = 8:2
–
2
3
−
8
Borondipyrromethene-based
Rhodamine-B hydrazide-based
Our work
H O/EtOH = 1:1
0.015
0.8916
0.4183
5.9 × 10
2
−
7
8
H O/DMSO = 1:1
1.59 × 10
1.38 × 10
2
−
H O
2
-
1
−
Figure 4. Emission intensity of DA (20 μmol L ) and DA + CN
50 equiv.) at different pH values. HEPES (4-(2-hydroxyerhyl)
(
-1
piperazine-1-erhanesulfonic acid) buffered water solution (1 mmol L )
λex = 315 nm, λem = 390 nm).
(
−
intensity of chemosensor DA + CN was not affected by the
−
−
presence of the other anions, especially F andAcO , which
−
demonstrated that DA has specific selectivity for CN .
The reversibility of the sensor is an extremely important
aspect for the detection of the specific analyses, so we
investigated the fluorescence behavior of chemosensor
−
+
−
DA between CN and H ions. The addition of CN ions
to the solution of chemosensor DA induced fluorescence
+
disappearing, with the addition of H , the fluorescence was
turn on. This reversible process of “on-off-on” could be
repeated at least three times with a little loss of fluorescent
intensity (Figure 7).
-
1
Figure 3. (a) Fluorescence spectra (λex = 315 nm) of DA (20 μmol L )
On the basis of the spectral results, the recognition
−
in the presence of different amounts of CN . Inset: a plot of fluorescence
intensity at 390 nm vs. number of equivalents of CN ; (b) Benesi-
−
−
mechanism of chemosensor DA with CN is proposed
−
Hilderbrand plot of DA with CN .
as follows: before the addition of cyanide anions, the

Vol. 29, No. 7, 2018
Wang et al.
1567
-1
Figure 5. Time-dependent fluorescence intensity of DA (20 μmol L ) in
the presence of 5 equiv. CN in pure water (λex = 315 nm, λem = 390 nm)
was recorded after 0, 1, 2, 4, 6 and 8 s.
−
-1
Figure 7. Fluorescence intensity of DA (20 μmol L ) upon the alternate
+
−
addition of CN and H in pure water.
−
indicating that the recognition of CN is a deprotonation
process. In addition, we prepared the carboxylate salt of DA
using sodium carbonate, and investigated its photophysical
properties. The results show the fluorescence spectrum of
−
−
DA and DA + CN have significant overlaps (Figure S4,
−
SI section), and prove that the recognition of CN is a
deprotonation process.
-
1
Figure 6. Emission intensity of DA (20 μmol L ) in the presence of
−
5
equiv. of other anions and DA + CN in the presence of 5 equiv. of other
anions in pure water (λex = 315 nm, λem = 390 nm).
intramolecular rotation was restricted by the hydrogen
bond. In this case, the sensor is in the intramolecular charge
transfer (ICT) state and displays a very strong fluorescence.
−
Figure 8. The proposed binding mechanism of DA for CN anion.
−
With the increasing addition of CN , the hydrogen bond
To study its practical applications, the chemosensor DA
was used to measuring CN in tap water. By adding a known
quantity of standard CN to tap water and calculating its
recovery, the accuracy of the method was evaluated. The
−
is destroyed, the benzene ring of chemosensor DA could
take place of an intramolecular rotation, and change to
twisted ICT (TICT) state and show a weak fluorescence
−
+
−
emission at 390 nm. With further adding H to solution of
recoveries of different known quantities of CN added were
−
DA + CN , the fluorescence intensity was recovered to an
gained from 96.6 to 103.6% with a favorable analytical
precision (relative standard deviation (RSD) ≤ 5.0%),
which indicated the chemosensor DA was able to determine
1
ICT state (Figure 8). Meanwhile, the H NMR titration
experiments were conducted to demonstrate the proposed
recognition mechanism. As shown in Figure 9, upon the
−
CN in tap water. The results were presented in Table S1
−
gradual addition of CN , the –COOH peak at 12.85 ppm
(SI section).
disappeared, and the signal peak of the hydrogen atoms of
the benzene ring and the naphthalene ring shifted upfield,
Motivated by the favorable characteristic of
chemosensor DA in solution, test strips were carried out

–
1
568
A Water Soluble Naphthalimide-Based Chemosensor for Fluorescent Detection CN in Pure Water
J. Braz. Chem. Soc.
1
−
-1
Figure 9. H NMR spectra of free DA (600 MHz, DMSO-d ) and in the presence of different amounts of CN (1 mol L , H O).
6
2
by submersing filter papers in the pure water solution of
a novel water soluble fluorescent chemosensor (DA).
As expected, DA displays high sensitivity and rapid
response (about 1 s) for recognizing CN in 100% water
−4
-1
DA (2.0 × 10 mol L ) and then dried in air. The test strips
−
−
coated with DA were utilized to sense CN and other anions,
similar to the pH test paper. As shown in Figure 10, when
solutions via an ICT-TICT state change mechanism. The
−
−4
-1
−
one drop of CN (2.0 × 10 mol L ) water solution was
added on the test kits, the fluorescence turn off response
can be observed by naked-eye under UV irradiation.
The same procedures were done for competitive ions.
However, potentially competitive ions had no influence
detection limits of the chemosensor DA toward CN was
−
8
-1
1.38 × 10 mol L , which was far below the WHO limit
-1
(1.9 μmol L ). Furthermore, the sensor DA was able to
−
determine CN in tap water with good recovery. Meanwhile,
we prepared the test strips based on DA, which could
−
−
on the detection of CN by the test strips. Hence, DA also
rapidly and efficiently detect CN in water.
−
possesses excellent selectivity for CN in test strips.
Supplementary Information
Supplementary information is available free of charge
at http://jbcs.sbq.org.br as PDF file.
Acknowledgments
This work was supported by the National Natural
Science Foundation of China (NSFC, No. 21661028;
2
1662031; 21574104), the Program for Changjiang
Figure 10. Photographs of DA on test strips (A) free DA; (B) after
submersing in pure water solutions of DA + CN ; (C) after submersing
Scholars and Innovative Research Team in University of
Ministry of Education of China (IRT 15R56).
−
in pure water solutions of DA + other anions; (D) after submersing in
−
pure water solutions of DA + CN + other anions using UV lamp at room
temperature.
References
Conclusions
1. Xu, Z.; Chen, X.; Kim, H. N.;Yoon.; J. Chem. Soc. Rev. 2010,
3
9, 127; Mannel-Croise, C.; Probst, B.; Zelder, F.; Anal. Chem.
In summary, by rationally introducing aromatic
carboxyl and 1,8-naphthalimide moieties, we designed
2009, 81, 9493; Vallejos, S.; Estevez, P.; Garcia, F. C.; Serna,
F.; de la Pena, J. L.; Garcia, J. M.; Chem. Commun. 2010, 46,

Vol. 29, No. 7, 2018
Wang et al.
1569
7
951; Kim, D.-S.; Chung, Y. M.; Jun, M.; Ahn, K. H.; J. Org.
11. Sun,Y. X.; Dong, W. K.; Wang, L.; Zhao, L.;Yang,Y. H.; Chin.
J. Inorg. Chem. 2009, 25, 1478; Dong, W. K.; Sun,Y. X.; Zhao,
C. Y.; Dong, X. Y.; Xu, L.; Polyhedron 2010, 29, 2087; Dong,
X. Y.; Sun, Y. X.; Wang, L.; Li, L.; J. Chem. Res. 2012, 387;
Wang, P.; Zhao, L.; Spectrochim. Acta, Part A 2015, 135, 342;
Dong, W. K.; Ma, J. C.; Zhu, L. C.; Sun, Y. X.; Akogun, S. F.;
Zhang, Y.; Cryst. Growth Des. 2016, 16, 6903.
Chem. 2009, 74, 4849; Rahman, S.;Assiri,Y;Alodhayb, A. N.;
Beaulieu, L. Y.; Oraby, A. K.; Georghiou, P. E.; New J. Chem.
2
016, 40, 434.
2
. Baskin, S. I.; Brewer, T. G. In Medical Aspects of Chemical
and Biological Warfare; Sidell, F.; Takafuji, E. T.; Franz, D.
R., eds.; TMM: Washington, 1997, p. 271.
3
4
. World Health Organization (WHO); Guidelines for Drinking-
Water Quality; World Health Organization: Geneva, 1996.
. Hu, J. H.; Sun,Y.; Qi, J.; Pei, P. X.; Lin, Q.; Zhang,Y. M.; RSC
Adv. 2016, 6, 100401; Jung, H. S.; Han, J. H.; Kim, Z. H.; Kang,
C.; Kim, J. S.; Org. Lett. 2011, 13, 5056; Kumar, S.; Singh, P.;
Hundal, G.; Hundal, M. S.; Subodh Kumar, S.; Chem. Commun.
12. Cheng, X.; Li, H.; Zheng, F.; Lin, Q.; Zhang, Y. M.; Yao, H.;
Wei, T. B.; Dyes Pigm. 2016, 127, 59; Wang, L.; Li, W. T.; Qu,
W. J.; Su, J. X.; Lin, Q.; Wei, T. B.; Zhang, Y. M.; Supramol.
Chem. 2017, 29, 489, DOI: 10.1080/10610278.2016.1277586;
Chang, J.; Cai, Y.; Wei, T. B.; Sens. Actuators, B 2015, 213,
501; Lin, Q.; Zhu, X.; Fu, Y. R.; Yang, Q.; Sun, B.; Wei, T. B.;
Zhang, Y. M.; Dyes Pigm. 2015, 113, 748; Qu, W. J.; Gao, G.
Y.; Shi, B. B.; Wei, T. B.; Zhang,Y. M.; Lin, Q.;Yao, H.; Sens.
Actuators, B 2014, 204, 368.
2013, 49, 2667; Sun,Y.; Hu, J. H.; Qi, J.; Li, J. B.; Spectrochim.
Acta, Part A 2016, 167, 101.
5
. Cort, A. D.; Forte, G.; Schiaffino, L.; J. Org. Chem. 2011,
7
6, 7569; Li, Y. P.; Yang, H. R.; Zhao, Q.; Song, W. C.; Han,
13. Hu, J. H.; Sun,Y.; Qi, J.; Li, Q.; Wei, T. B.; Spectrochim. Acta,
Part A 2017, 175, 125; Wang, F.; Xu, Y. L.; Aderinto, S. O.;
Peng, H. P.; Zhang, H.; Wu, H. L.; J. Photochem. Photobiol., A
2017, 332, 273; Aderinto, S. O.; Zhang, H.; Wu, H. L.; Chen,
C. Y.; Zhang, J. W.; Peng, H. P.; Yang, Z. H.; Wang, F.; Color.
Technol. 2017, 133, 40; Wu, H. L.; Aderinto, S. O.; Xu, Y. L.;
Zhang, H.; Fan, X. Y.; J. Appl. Spectrosc. 2017, 84, 25;Yu, B.;
Li, C.Y.; Sun,Y. X.; Jia, H. R.; Guo, J. Q.; Li, J.; Spectrochim.
Acta, Part A 2017, 184, 249.
J.; Bu, X. H.; Inorg. Chem. 2012, 51, 9642; Hu, J. H.; Li, J.
B.; Qi, J.; Chen, J. J.; New J. Chem. 2015, 39, 843; Dong, W.
K.; Akogun, S. F.; Zhang, Y.; Sun, Y. X.; Dong, X. Y.; Sens.
Actuators, B 2017, 238, 723; Hu, J. H.; Li, J. B.; Qi, J.; Sun,
Y.; Sens. Actuators, B 2015, 208, 581.
6
. Guliyev, R.; Buyukcakir, O.; Sozmen, F.; Bozdemir, O. A.;
Tetrahedron Lett. 2009, 50, 5139; Gee, H. C.; Lee, C. H.;
Jeong, Y. H.; Jang, W. D.; Chem. Commun. 2011, 47, 11963;
Sharma, N.; Reja, S. I.; Bhalla, V.; Kumar, M.; Dalton Trans.
14. Reger, D. L.; Debreczeni,A.; Horger, J. J.; Smith, M. D.; Cryst.
Growth Des. 2011, 11, 4068.
2
014, 43, 15929; Chawla, H. M.; Shukla, R.; Goel, P.; New J.
Chem. 2014, 38, 5264; Jo, H. Y.; Park, G. J.; Na, Y. J.; Choi, Y.
W.; You, G. R.; Kim, C.; Dyes Pigm. 2014, 109, 127.
15. Wang, F.; Gao, L.; Zhao, Q.; Zhang, Y.; Dong, W. K.; Ding, Y.
J.; Spectrochim. Acta, Part A 2018, 190, 111.
7
8
. Li, X. H.; Gao, X. H.; Shi, W.; Ma, H. M.; Chem. Rev. 2014,
16. Li, J. J.; Wei, W.; Qi, X. L.; Zuo, G. C.; Fang, J. K.; Dong, W.;
Sens. Actuators, B 2016, 228, 330.
1
14, 590.
. Chung, S. Y.; Nam, S. W.; Lim, J.; Park, S.; Yoon, J.; Chem.
Commun. 2009, 2866; Chen, X.; Nam, S. W.; Kim, G. H.; Song,
N.; Jeong, Y.; Shin, I.; Kim, S. K.; Kim, J.; Park, S.; Yoon, J.;
Chem. Commun. 2010, 46, 8953; You, G. R.; Park, G. J.; Lee,
J. J.; Kim, C.; Dalton Trans. 2015, 44, 9120; Xu, J. F.; Chen,
H. H.; Chen, Y. Z.; Li, Z. J.; Wu, L. Z.; Tung, C. H.; Yang, Q.
Z.; Sens. Actuators, B 2012, 168, 14.
17. Shi, B. B.; Zhang, P.; Wei, T. B.; Yao, H.; Lin, Q.; Zhang, Y.
M.; Chem. Commun. 2013, 49, 7812.
18. Xiao, K.; Nie, H. M.; Gong, C. B.; Qu, X. X.; Tang, Q.; Chow,
C. F.; Dyes Pigm. 2015, 116, 82.
19. Hu, J. W.; Lin, W. C.; Hsiao, S.Y.; Wu,Y. H.; Chen, K.Y.; Chen,
H. W.; Sens. Actuators, B 2016, 233, 510.
20. Yang, L.; Li, X.; Qu, Y.; Qu, W.; Zhang, X.; Hang, Y.; Ågren,
H.; Hua, J.; Sens. Actuators, B 2014, 203, 833.
9
. Ma, T. H.; Dong, M.; Dong,Y. M.; Wang,Y. W.; Peng,Y.; Chem.
Eur. J. 2010, 16, 10313.
21. Wang, S. T.; Sie, Y. W.; Wan, C. F.; Wu, A. T.; J. Lumin. 2016,
173, 25.
1
0. Duke, R. M.; Veale, E. B.; Pfeffer, F. M.; Kruger, P. E.;
Gunnlaugsson, T.; Chem. Soc. Rev. 2010, 39, 3936; Zheng, S.
P. L.; Lynch, P. L. M.; Rice, T. E.; Moody, T. S.; Gunaratne,
H. Q. N.; de Silva, A. P.; Photochem. Photobiol. Sci. 2012, 11,
22. Yu, Y. H.; Shu, T. T.; Yu, B. J.; Deng, Y.; Fu, C.; Gao, Y. G.;
Dong, C. Z.; Ruan, Y. B.; Sens. Actuators, B 2018, 255, 3170.
23. Pei, P. X.; Hu, J. H.; Ni, P. W.; Long, C.; Su, J. X.; Sun, Y.;
RSC Adv. 2017, 7, 46832.
1
675; Banerjee, S.; Veale, E. B.; Phelan, C. M.; Murphy, S. A.;
Tocci, G. M.; Gillespie, L. J.; Frimannsson, D. O.; Kelly, J. M.;
Gunnlaugsson, T.; Chem. Soc. Rev. 2013, 42, 1601; Reger, D.
L.; Leitner, A. P.; Smith, M. D.; Cryst. Growth Des. 2016, 16,
Submitted: November 24, 2017
Published online: February 23, 2018
5
27.
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