A cyanide-triggered hydrogen-bond-breaking deprotonation mechanism: Fluorescent detection of cyanide using a thioacetohydrazone-functionalized bispillar[5]arene

Article abstract of DOI:10.1039/c7nj03937a

A novel sensor (AHP5) comprising a thioacetohydrazone-bridged bispillar[5]arene was developed and shown to fluorescently sense cyanide ions. The sensor manifested a response specific to cyanide over other common anions (SCN^-, AcO^-, H

Full text of DOI:10.1039/c7nj03937a

View Article Online
View Journal
NJC
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: T. Wei, J. Ding, J.
Chen, B. Han, X. Jiang, H. Yao, Y. Zhang and Q. Lin, New J. Chem., 2017, DOI: 10.1039/C7NJ03937A.
Volume 40 Number
1
January 2016 Pages 1–846
This is an Accepted Manuscript, which has been through the
Royal Society of Chemistry peer review process and has been
accepted for publication.
NJC
New Journal of Chemistry
www.rsc.org/njc
A journal for new directions in chemistry
Accepted Manuscripts are published online shortly after
acceptance, before technical editing, formatting and proof reading.
Using this free service, authors can make their results available
to the community, in citable form, before we publish the edited
article. We will replace this Accepted Manuscript with the edited
and formatted Advance Article as soon as it is available.
You can find more information about Accepted Manuscripts in the
author guidelines.
Please note that technical editing may introduce minor changes
to the text and/or graphics, which may alter content. The journal’s
standard Terms & Conditions and the ethical guidelines, outlined
in our author and reviewer resource centre, still apply. In no
event shall the Royal Society of Chemistry be held responsible
for any errors or omissions in this Accepted Manuscript or any
consequences arising from the use of any information it contains.
ISSN 1144-0546
PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
rsc.li/njc

Please do not adjust margins
New Journal of Chemistry
Page 1 of 5
View Article Online
DOI: 10.1039/C7NJ03937A
Journal Name
ARTICLE
A cyanide triggered hydrogen bonds breakage deprotonation
–
mechanism: fluorescent detection of CN using a
thioacetohydrazone functionalized bispillar[5]arene
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Tai
-Bao Wei,* Jin-Dong Ding, Jin-Fa Chen, Bing-Bing Han, Xiao-Mei Jiang, Hong Yao, You-Ming
www.rsc.org/
Zhang and Qi Lin *
A novel sensor (AHP5) involving a thioacetohydrazone bridged bispillar[5]arene was developed and demonstrated to
–
–
–
–
4
fluorescently sense CN . It manifested specificity response for cyanide over other common anions (SCN , AcO , HSO ,
–
–
–
–
–
–
2 4 4 2
H PO , I , Br , ClO , Cl and F ) in DMSO/H O (9 : 1, v/v) solution. Upon treatment with cyanide, AHP5 exhibited a
significant fluorescence response, simultaneously with the remarkable changes in its fluorescence spectra. In addition,
competitive anions did not show any obviously influence on the probing behavior. Notably, the investigation of the
–
recognition mechanism indicated that AHP5 recognized CN by a deprotonated procedure accompanied with the breakage
of intermolecular hydrogen bonds. Furthermore, the sensor was successfully applied to the detection of cyanide in
cyanide–containing water samples.
Generally cyanide is present in the seeds of apricots, sprouting
1
1
Introduction
potatoes and cigarette smoke etc. Cyanide poisoning can lead to
vomiting, loss of consciousness, respiratory arrest and eventual
As a new kind of emerging macrocyclic compounds next to
12
1
2
3
4
death. According to the World Health Organization, the maximum
crown ethers, cyclodextrins, calixarenes, and cucurbiturils,
pillar[n]arenes, which are cyclized by hydroquinone units linked
with methylene bridges at 2,5 positions of the benzene moieties,
acceptable concentration level of cyanide in drinking water is 1.9
13
μM. Moreover, optical sensors for the detection of cyanide anions,
–
5
in which a change in color or fluorescence intensity (or emission
wavelength) is monitored, have received significant attention due
to their simplicity, inexpensive, high selectivity and rapid
have been studied actively since they were found in 2008. The
highly symmetrical and rigid structures along with easy
functionalization of pillar[n]arenes shown fascinating host
–
guest
14
implementation nature in recent years. Accordingly, the design
binding properties with a number of guest molecules, which have
6
and synthesis of optical sensors for specific detection of cyanide
have been an important task.
captured more and more attention of scientists in recent years.
Thus far, the use of host–guest interactions involving
In view of this and as part of our research interest in
pillar[n]arenes and inorganic anions were very limited and only a
few publications involve recognition of cyanide by pillar[n]arenes
7
as receptors. It is noteworthy that bispillar[n]arene-based cyanide
15
pillar[n]arenes chemistry and ions recognition, we designed and
synthesized
a
novel fluorescent sensor AHP5 involving
a
8
thioacetohydrazone
bridged bispillar[5]arene. The
sensor has been unreported to date. Therefore, the design and
thioacetohydrazone bridged AHP5 was successfully obtained in 31%
yield by condensation reaction of benzaldehyde functionalized
pillar[5]arene and thioacetohydrazide functionalized pillar[5]arene.
synthesis of novel functionalized bispillar[n]arenes is particularly
important.
The recognition of anions has received continuously and
significant attention due to their important roles in biological,
16
In addition, acylhydrazone group is a good ions recognition site.
–
9
The sensor AHP5 could fluorescently sense CN anion with high
industrial, clinical, and environmental processes. As a Janus anion
-8
−1
selectivity and sensitivity (5.14×10 mol·L ). In addition, the
competitive anions did not show any obviously influence on the
probing behavior. Furthermore, the recognition mechanism was
in chemistry, cyanide anion, has been continuously of concern all
over the world due to its high toxicity and widespread use in
industrial processes, such as paper, textiles, and plastics
1
1
0
studied by H NMR, Job's plot measurement and electrospray
manufacturing, metallurgy, herbicide production and so forth.
ionization mass spectrometry. Notably, the investigation indicated
–
that AHP5 recognized CN by
a deprotonated procedure
accompanied with the breakage of intermolecular hydrogen bonds.
More importantly, this is the first example that a bispillar[5]arene
based sensor was synthesized for fluorescent recognition of cyanide
Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of
Education of China; Key Laboratory of Polymer Materials of Gansu Province;
College of Chemistry and Chemical Engineering, Northwest Normal University,
Lanzhou, Gansu, 730070, P. R. China Fax: +86 9317973191; Tel: +86
-
anion in DMSO/H
2
O (9 : 1, v/v) solution
.
9317973191; E-mail: weitaibao@126.com; linqi2004@126.com.
1
Electronic Supplementary Information (ESI) available: Characterizations, H NMR
date and other materials. See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
Please do not adjust margins

Please do not adjust margins
New Journal of Chemistry
Page 2 of 5
View Article Online
DOI: 10.1039/C7NJ03937A
ARTICLE
Journal Name
Scheme 1 The synthesis of bispillar[5]arene AHP5
.
-
4
Fig. 1 Fluorescence spectral response of AHP5 (2.0 × 10 M) in
DMSO/H O (9 : 1, v/v) in the presence of cyanide and other anions
5.0 equiv.). Inset: color changes observed for AHP5 upon the
2
(
–
–
–
–
–
–
–
–
–
–
addition of SCN , AcO , HSO , CN , H PO , I , Br , ClO , Cl and F
4
2
4
4
Results and discussion
2
in DMSO/H O (v/v =9 : 1) solution on a spot plate.
–
In order to investigate the CN recognition abilities of the sensor
2
AHP5 in DMSO/H O (9 : 1, v/v) solution, a series of host–guest
recognition experiments were carried out. The sensor AHP5 toward
–
–
–
–
–
–
–
various anions (including SCN , AcO , HSO
4
, CN , H
2 4
PO , I , Br ,
–
–
–
ClO
4
, Cl and F ) were primarily investigated using fluorescence
spectroscopy. In the fluorescence spectrum, the maximum emission
of AHP5 appeared at 504 nm in DMSO/ H O (9: 1, v/v) while excited
2
–
at λex = 420 nm. When 5.0 equiv. of CN was added to the solution
of the sensor AHP5, the fluorescence emission band was red–
shifted to 504 nm, and an approximate 9.0–fold fluorescence
enhancement was observed (Fig. S19). In addition, a strong
chartreuse fluorescence appeared. In comparison, the same tests
–
–
–
–
–
–
–
–
–
4 2 4 4
were applied using SCN , AcO , HSO , CN , H PO , I , Br , ClO , Cl
–
–
and F anions, and only CN have significant changes in the
fluorescence spectrum of the sensor (Fig. 1), and none of those
other anions induced any significant changes in the fluorescent
–
spectrum of the sensor. Upon addition of CN anion, the band was
red–shifted accompanied with its emission intensity significantly
enhanced at 504 nm. The apparent color change from colorless to
chartreuse could be distinguished under the UV lamp. Therefore, in
Fig. 2 Fluorescence spectra of AHP5 (0.2 mM) in the presence of
–
different concentration of CN in DMSO/H O (9 : 1, v/v) solution.
2
Inset: a) a plot of fluorescence intensity depending on the
2
DMSO/H O (9 : 1, v/v) solution, AHP5 showed specific fluorescence
–
–
concentration of CN in the range from 0 to 1.6 equiv. Each
selectivity to CN anion.
measurement was done at room temperature of mixing for AHP5
To further investigate the efficiency of the sensor AHP5 toward
–
–
and CN in DMSO/H O (9 : 1, v/v). b) color changes observed for
2
CN detection, we carried out fluorescence emission titration
–
AHP5 upon the addition of CN .
experiments. The emission spectral variation of AHP5 upon gradual
–
addition of CN anion is shown in Fig. 2. In the fluorescence
–
To further explore the utility of sensor AHP5 as an anion–
spectrum, upon addition of increasing amounts of CN anions (0–
–
selective chemosensor for CN , competitive experiments were
2
1.4 equiv.) to the solution of AHP5 in DMSO/H O (9:1, v/v), the
–
carried out in the presence of 5.0 equiv. of CN and 1.0 equiv. of
fluorescence emission at 478 nm is gradually red–shifted to 504 nm,
directly leading to a strong chartreuse emission. The detection limit
of the fluorescent spectrum changes calculated on the basis of 3σ/S
–
–
–
–
–
–
various other anions (including SCN , AcO , HSO
4
, CN , H
2 4
PO , I ,
–
–
–
–
Br , ClO , Cl and F ) in DMSO/H O (9 : 1, v/v) solution. The
4 2
-8
–
fluorescence selectivity was examined at an emission wavelength of
504 nm, all the competing anions did not interfere in the detection
is 5.14×10 M for CN (Fig. S20), which is far lower than the WHO
-1
guideline of 1.9 μmol L cyanide.
–
of CN (Fig. 3). This result indicated high selectivity of the sensor
–
AHP5 toward CN over other analytes mentioned above.
2
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Please do not adjust margins
Page 3 of 5
New Journal of Chemistry
View Article Online
DOI: 10.1039/C7NJ03937A
Journal Name ARTICLE
1
Fig. 4 H NMR spectra (600 MHz, 298 K) of AHP5 in DMSO–d
6
at
various concentrations: (a) 2.0 mM; (b) 10.0 mM; (c) 20.0 mM; (d)
5
0.0 mM; (e) 120.0 mM.
Fig. 3 Fluorescence of the sensor AHP5 at 504 nm with addition of
–
5.0 equiv. of CN in the presence of 1.0 equiv. of other anions in
2
DMSO/H O (v/v = 9 : 1) solution.
1
The recognition mechanism was investigated by H NMR, Job's
1
plot measurement and ESI–MS. In the concentration dependent H
NMR of AHP5 (Fig. 4), with the concentration of AHP5 rising, the
signals of H1 and H2 showed obvious downfield shifts, which
1 2
indicated that H and H formed stable intermolecular hydrogen
1
bonds with –C=O on adjacent molecule. Besides, H NMR titration
displayed the chemical shift changes of AHP5 upon the addition of
–
CN . As shown in Fig. 5, the proton of –NH– showed two peaks at
6
11.3 and 11.4 ppm in DMSO–d , which were due to the impact of
tautomerism. The presence of cyanide anions could taking the
proton away via deprotonating during the thioacetohydrazone
1
moieties of AHP5 and cyanide itself. In the corresponding H NMR
–
spectra, upon addition of 1.0 equiv. CN by DMSO–d
6
solution, the
signal at 11.3 and 11.4 ppm (–NH–) disappeared. Meanwhile, the
intermolecular hydrogen bonds among H , H and –C=O were
1
2
1
destroyed. This is a novel recognition mechanism of AHP5 Fig. 5 Partial H NMR spectra of AHP5 (DMSO–d ) and in the
6
–
encounter CN occurred deprotonation effect accompanied with presence of varying amounts of cyanide anions (0.1 M, DMSO–d
6
).
the breakage of intermolecular hydrogen bonds. In addition, the
fluorescence of Job's plot measurement was conducted by varying
–
the concentration of both AHP5 and CN (Fig. S21). The inflection
–
point appears at the mole fraction of 0.5, indicated AHP5 and CN
were formed a 1:1 stoichiometry. It was further confirmed by the
appearance of a peak at m/z 1864.7559 which can be assignable to
+
[
AHP5–H+2Na] in the ESI-MS (Fig. S22). These common
phenomenon could be explained from the propose sensing
mechanism show in Scheme 2.
Scheme 2 The proposed sensing mechanism of the sensor
–
AHP5 to CN .
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
Please do not adjust margins

Please do not adjust margins
New Journal of Chemistry
Page 4 of 5
View Article Online
DOI: 10.1039/C7NJ03937A
ARTICLE
Journal Name
Conclusions
In summary, we have developed
a thioacetohydrazone
–
functionalized bispillar[5]arene, which could detect CN with
-8
−1
specific selectivity and high sensitivity (5.14×10 mol·L ). The
investigation of the recognition mechanism indicated that the
–
sensor AHP5 recognized CN by a deprotonated procedure
accompanied with the breakage of intermolecular hydrogen bonds.
More importantly, this is the first example that a bispillar[5]arene-
based sensor was synthesized for fluorescent recognition of cyanide
2
anion in DMSO/ H O (9 : 1, v/v) solution. Therefore, this novel
cyanide triggered hydrogen bonds breakage deprotonation
mechanism will extend the application of pillar[n]arenes.
Fig. 6 Fluorescence spectral response of the sensor AHP5 to detect
Acknowledgements
cyanide in water sample.
This work was supported by the National Natural Science
We also investigated the practical utilities of the sensor in our Foundation of China (NSFC) (No. 21662031; 21661028; 21574104;
daily life, we selected the water samples containing cyanide whose 21262032) and the Program for Changjiang Scholars and Innovative
concentration was unknown to carry out the below experiment. Research Team in University of Ministry of Education of China (IRT
Some distilled water and some cyanide–containing DMSO solution 15R56).
were added in a 10 ml burette. The burette was shaken for 5
minutes, and then this solution was used as water sample. The
fluorescence emission spectrum of AHP5 (0.2 mM in 4.5 mL DMSO) Notes and references
is shown as black line in Fig. 6, then, upon the titration of water
1
(a) F. Huang, F. R. Fronczek and H. W. Gibson, J. Am. Chem.
Soc., 2003, 125, 9272; (b) Z. Niu, F. Huang and H. W.
Gibson, J. Am. Chem. Soc., 2011, 133, 2836; (c) Y.-S. Su, J.-
W. Liu, Y. Jiang and C.-F. Chen, Chem. Eur. J., 2011, 17,
2435; (d) M. Zhang, D. Xu, X. Yan, J. Chen, S. Dong, B.
Zheng and F. Huang, Angew. Chem., Int. Ed., 2012, 51,
sample (0.5 mL) red line is obtained. The cyanide concentration of
-5
samples was 5.83×10 M calculated by the linear equation of
–
minimum detection limit of AHP5 with CN (Fig. S20). Therefore, the
–
sensor could conveniently detect CN in water, confirming that
–
AHP5 is a promising CN probe for practical applications.
7
011; (e) S. Li, G.-H. Weng, W. Lin, Z.-B. Sun, M. Zhou, B.
The detection limit is one of the most important parameters in
ion sensing. For many practical purposes, it is very important to
detect the analytes at low concentrations. The fluorimetric
Zhu, Y. Ye and J. Wu, Polym. Chem., 2014, 5, 3994.
2
3
(a) Q.-C. Wang, D.-H. Qu, J. Ren, K. Chen and H. Tian,
Angew. Chem., Int. Ed., 2004, 43, 2661; (b) A. Harada, Y.
Takashima and H. Yamaguchi, Chem. Soc. Rev., 2009, 38,
–
detection limits of sensor AHP5 for CN were also determined. As
–
8
75; (c) T. Liu, X. Li, Y. Qian, X. Hu and S. Liu,
shown in Fig. S23, the minimum concentration of CN that could be
Biomaterials, 2012, 33, 2521.
(a) D.-S. Guo and Y. Liu, Chem. Soc. Rev., 2012, 41, 5907; (b)
observed though one order of magnitude lower for fluorescence
-4
naked eye detection was 5 × 10 M, by using a UV lamp at 365 nm.
Finally, to investigate the practical application of AHP5, a thin
film was prepared by immersing a glass sheet into a high
concentration solution of AHP5 (0.1 M) and then drying it in air. The
Q. Zhang, X. Yao, D.-H. Qu and X. Ma, Chem. Commun.
,
2
014, 50, 1567; (c) X. Yao, T. Li, S. Wang, X. Ma and H.
Tian, Chem. Commun., 2014, 50, 7166; (d) H. Li, L.-L. Tan,
P. Jia, Q.-L. Li, Y.-L. Sun, J. Zhang,Y.-Q. Ning, J. Yu and
Y.-W. Yang, Chem. Sci., 2014, 5, 2804.
–
–
thin film was utilized to sense CN . As shown in Fig. 7, when CN
4
(a) W.-H. Huang, P. Y. Zavalij and L. Isaacs, Angew. Chem.,
Int. Ed., 2007, 46, 7425; (b) J. M. Zayed, N. Nouvel, U.
Rauwald and O. A. Scherman, Chem. Soc. Rev., 2010, 39,
were added onto the thin film, the obvious color change was
observed under irradiation at 365 nm using a UV lamp. Therefore,
–
the thin film could be a convenient test kit for detecting CN .
2
806; (c) E. A. Appel, J. Barrio, X. J. Loh and O. A.
Scherman, Chem. Soc. Rev., 2012, 41, 6195; (d) H. Yang, Y.
Bai, B. Yu, Z. Wang and X. Zhang, Polym. Chem., 2014, 5,
6
439.
5
6
(a) T. Ogoshi, S. Kanai, S. Fujinami, T. Yamagishi and Y.
Nakamoto, J. Am. Chem. Soc., 2008, 130, 5022; (b) D. Cao,
Y. Kou, J. Liang, Z. Chen, L. Wang and H. Meier, Angew.
Chem. Int. Ed., 2009, 48, 9721; (c) Y. Yao, M. Xue, Z.
Zhang, M. Zhang, Y. Wang and F. Huang, Chem. Sci., 2013,
4
, 3667.
(a) N. L. Strutt, R. S. Forgan, J. M. Spruell, Y. Y. Botros and
J. F. Stoddart, J. Am. Chem. Soc., 2011, 133, 5668; (b) Z.
Zhang, C. Han, G. Yu and F. Huang, Chem. Sci., 2012, 3,
3026; (c) Y. Cao, X.-Y. Hu, Y. Li, X. Zou, S. Xiong, C. Lin,
Y.-Z. Shen and L. Wang, J. Am. Chem. Soc., 2014, 136,
–
Fig. 7 Photos of the thin film utilized to sense CN under irradiation
at 365 nm using a UV lamp.
1
0762; (d) X. Chi, X. Ji, D. Xia and F. Huang, J. Am. Chem.
Soc., 2015, 137, 1440; (e) X.-Y. Hu, K. Jia, Y. Cao, Y. Li, S.
Qin, F. Zhou, C. Lin, D. Zhang and L. Wang, Chem. Eur. J.
,
4
| J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Please do not adjust margins
New Journal of Chemistry
Page 5 of 5
View Article Online
DOI: 10.1039/C7NJ03937A
Journal Name ARTICLE
2015, 21, 1208; (f) X. Wu, Y. Yu, L. Gao, X.-Y. Hu and L.
Chen, X.-B. Cheng, H. Li, B.-B. Han, Y.-M. Zhang, H. Yao
Wang, Org. Chem. Front., 2016, 3, 966.
(a) J. S. Mugridge, R. G. Bergman and K. N. Raymond, J. Am. 16 (a)W.-J. Qu, W.-T. Li, H.-L. Zhang, T.-B. Wei, Q. Lin, H.
and Q. Lin, Org. Chem. Front., 2017, 4, 210.
7
Chem. Soc., 2010, 132, 1182; (b) M. Xue, Y. Yang, X. Chi,
Z. Zhang and F. Huang, Acc. Chem. Res., 2012, 45, 1294; (c)
G .Yu, B. Hua, and C. Han, Org. Lett., 2014, 16, 2486; (d) X.
Cheng, H. Li, F. Zheng, Q. Lin, Y. Zhang, H. Yao and T.
Wei, Dyes and Pigments, 2016, 127, 59; (e) P. M. Reddy, S.-
R. Hsieh, J.-K. Chen, C.-J. Chang, J.-Y. Kang and C.-H.
Chen, Spectrochim. Acta, Part A, 2017, 186, 8.
Yao and Y.-M. Zhang, Sens. Actuators, B, 2017, 241, 430;
(b) T.-B. Wei, J.-F. Chen, X.-B. Cheng, H. Li, B.-B. Han, H.
Yao, Y.-M. Zhang and Q. Lin, Polym. Chem., 2017, 8, 2005;
(c) Q. Lin, X. Zhu, Y.-P. Fu, Q.-P. Yang, B. Sun,T.-B.
Wei,Y.-M. Zhang, Dyes and Pigments, 2015, 113, 748.
8
(a) P. Wang, Y. Yao and M. Xue, Chem. Commun., 2014, 50,
Color Graphic:
5064; (b) W. Xia, M. Ni, C. Yao, X. Wang, D. Chen, C. Lin,
X.-Y. Hu and L. Wang, Macromolecules, 2015, 48, 4403; (c)
L.-L. Tan, H. Li, Y.-C. Qiu, D.-X. Chen, X. Wang, R.-Y.
Pan, Y. Wang, S. X.-A. Zhang, B. Wang and Y.-W. Yang,
Chem. Sci., 2015, 6, 1640; (d) Y. Fang, C. Li, L. Wu, B. Bai,
X. Li, Y. Jia, W. Feng and L. Yuan, Dalton Trans., 2015, 44,
14584; (e) X. Kuang, A. Wajahat, W. Gong, M. K.
Dhinakaran, X. Li and G. Ning, Soft Matter, 2017, 13, 4074.
(a) P. A. Gale, Chem. Commun., 2008, 0, 4525; (b) J. W.
Steed, Chem. Soc. Rev., 2009, 38, 506; (c) M. Dong, Y. Peng,
Y.-M. Dong, N. Tang, and Y.-W. Wang, Org. Lett., 2012, 14,
9
1
130; (d) X. Ji, Y.Yao, J. Li, X. Yan, and F. Huang, J. Am.
Chem. Soc., 2013, 135 ,74; (e) D.-H. Qu, Q.-C. Wang, Q.-W.
Zhang, X. Ma and H. Tian, Chem. Rev., 2015, 115, 7543.
0 (a) Z. Xu, X. Chen, H. N. Kima and J. Yoon, Chem. Soc.
Rev., 2010, 39, 127; (b) J. H. Lee, A. R. Jeong, I.-S. Shin,
H.-J. Kim, and J.-I. Hong, Org. Lett., 2010, 12, 764; (c) H.
Li, Z. Wen, L. Jin, Y. Kan and B. Yin, Chem. Commun.
,
,
2012, 48, 11659; (d) K. H. Jung and K.-H. Lee, Anal. Chem.
2
015, 87 , 9308; (e) Y.-X. Hua, Y. Shao, Y.-W. Wang and Y.
Text:
Bispillar[5]arene–based fluorescent sensor was used for
Peng, J. Org. Chem., 2017, 82, 6259; (f) P.-X. Pei, J.-H. Hu ,
Y. Chen, Y. Sun and J. Qi. Spectrochim. Acta, Part A, 2017,
fluorescence detection cyanide anion by
a deprotonated
181, 131.
procedure accompanied with the breakage of intermolecular
hydrogen bonds.
1
1
1
1 (a) F. H. Zelder, Inorg. Chem., 2008, 47, 1264; (b) Z. Dai and
E. M. Boon, J. Am. Chem. Soc., 2010, 132, 11496; (c) J. Ma,
P. K. Dasgupta, Anal. Chim. Acta, 2010, 673, 117; (d) R.
Jackson, R. P. Oda, R. K. Bhandari, S. B. Mahon, M.
Brenner, G. A. Rockwood and B. A. Logue, Anal. Chem.
,
2014, 86, 1845; (e) G. Volpi, J. Chem. Educ., 2016, 93 , 891.
2 (a) L. Deng, C. Chen, M. Zhou, S. Guo, E. Wang and S.
Dong, Anal. Chem., 2010, 82 ,4283; (b) W.-J. Qu, T.-B. Wei,
Q. Lin, W.-T. Li, J.-X. Su, G.-Y. Liang and Y.-M. Zhang,
Sens. Actuators, B, 2016, 232, 115; (c) Z. Shojaeifard, B.
Hemmateenejad and M. Shamsipur, ACS Appl. Mater.
Interfaces, 2016, 8, 15177.
3 (a) D. Shan,C. Mousty and S. Cosnier, Anal. Chem., 2004, 76,
178; (b) J. Liu, Y. Liu, Q. Liu, C. Li, L. Sun and F. Li, J. Am.
Chem. Soc., 2011, 133 , 15276; (c) Y. Sun, J.-H. Hu, J. Qi
and J.-B. Li, Spectrochim. Acta, Part A, 2016, 167, 101; (d)
N. Maurya and A. K. Singh, Dyes and Pigments, 2017, 147,
484; (e) Z. Shi, Y. Tu, R. Wang, G. Liu and S. Pu, Dyes and
Pigments, 2018, 149, 764.
1
4 (a) N.-Y. Kang, H.-H. Ha, S.-W. Yun, Y. H. Yu and Y.-T.
Chang, Chem. Soc. Rev., 2011,40, 3613; (b) X. Huang, X.
Gu, G. Zhang and D. Zhang, Chem. Commun., 2012, 48,
12195; (c) X. Cheng, Y. Zhou, J. Qin and Z. Li, ACS Appl.
Mater. Interfaces, 2012, 4, 2133; (d) B. Shi, P. Zhang, T.
Wei, H. Yao, Q. Lin and Y. Zhang, Chem. Commun., 2013,
4
9, 7812; (e) F. Wang, L.Wang, X.Chen and J.Yoon, Chem.
Soc. Rev., 2014, 43, 4312.
1
5 (a) B. Shi, P. Zhang, T. Wei, H. Yao, Q. Lin and Y. Zhang,
Chem. Commun., 2013, 49, 7812; (b) B. Shi, P. Zhang, T.
Wei, H.Yao, Q. Lin; J. Liu and Y. Zhang, Tetrahedron, 2013,
6
9, 7981; (c) Q. Lin, T.-T. Lu, X. Zhu, B. Sun, Q.-P. Yang,
T.-B. Wei and Y.-M. Zhang, Chem. Commun., 2015, 51,
635; (d) Q. Lin, T.-T. Lu, X. Zhu, T.-B. Wei, H. Li and Y.-
M. Zhang, Chem. Sci., 2016, 7, 5341; (e) T.-B. Wei, J.-F.
1
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins