Novel Fluorescent Chemosensor for Detection of F‾ Anions
Scheme 2 The proposed structures of PN-Fe for F ion
Y.; Liu, Y.; Liu, Y. Asian J. Org. Chem. 2016, 5, 321; (e) Yu, G.; Han,
C.; Zhang, Z.; Chen, J.; Yan, X.; Zheng, B.; Huang, F. J. Am. Chem.
Soc. 2012, 134, 8711; (f) Chi, X.; Ji, X.; Xia, D.; Huang, F. J. Am.
Chem. Soc. 2015, 137, 1440; (j) Shi, B.; Jie, K.; Zhou, Y.; Zhou, J.;
Xia, D.; Huang, F. J. Am. Chem. Soc. 2016, 138, 80; (h) Zhang, Z.;
Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F. Angew. Chem.,
Int. Ed. 2011, 50, 1397; (i) Yu, G.; Xue, M.; Zhang, Z.; Li, J.; Han,
C.; Huang, F. J. Am. Chem. Soc. 2012, 134, 13248.
[5] (a) Cao, Y.; Li, Y.; Hu, X.; Zou, X.; Xiong, S.; Lin, C.; Wang, L.
Chem. Mater. 2015, 27, 1110; (b) Wei, P.; Li, D.; Shi, B.; Wang, Q.;
Huang, F. Chem. Commun. 2015, 51, 15169; (c) Wu, X.; Li, Y.; Lin,
C.; Hu, Y.; Wang, L. Chem. Commun. 2015, 51, 6832; (d) Liao, X.;
Guo, L.; Chang, J.; Liu, S.; Xie, M.; Chen, G. Macromol. Rapid
Commun. 2015, 36, 1492; (e) Jie, K.; Zhou, Y.; Yao, Y.; Shi, B.;
Huang, F. J. Am. Chem. Soc. 2015, 137, 10472; (f) Wang, S.; Wang,
Y.; Chen, Z.; Lin, Y.; Weng, L.; Han, K.; Li, J.; Jia, X.; Li, C. Chem.
Commun. 2015, 51, 3434; (i) Li, C.; Han, K.; Li, J.; Zhang, Y.; Chen,
W.; Yu, Y.; Jia, X. Chem. Eur. J. 2013, 19, 1189.
[6] (a) Miao, F.; Zhou, J.; Tian, D.; Li, H. Org. Lett. 2012, 14, 3572; (b)
Xu, M.; Yin, C.; Huo, F.; Zhang, Y.; Chao, J. Sens. Actuators B:
Chem. 2014, 204, 18; (c) Mi, K.; Hyun, J.; Su, Y.; Suk, C.; Min, H.
Chem. Commun. 2009, 4838; (d) Ding, Y.; Xie, Y.; Li, X.; Jonathan,
P. H.; Zhang, W.; Zhu, W. Chem. Commun. 2011, 47, 5431; (e) Li, J.;
Hu, Q.; Yu, X.; Zeng, Y.; Cao, C.; Liu, X.; Pan, Z. J. Fluoresc. 2011,
21, 2005; (f) Anbu, S.; Ravishankaran, R.; Silva, M.; Karande, A. A.;
Pombeiro, A. J. L. Inorg. Chem. 2014, 53, 6655.
Conclusions
In conclusion, we synthesized a new class of super-
molecule recognition host based on a single functional-
+
ized pillar[5]arene. It was utilized to monitor Fe3 ions.
All of experiments indicated metal ions complexation
with the nitrogen atoms of PN, leading to its fluores-
cence decrease. The fluorescence of PN increased when
anions coordinated to metal ions from nitrogen atoms of
sensor PN. The detection limit of the F‾ anion was
2.50×10−7 mol/L. It was lower than the WHO permis-
sible limit of fluoride in India which has been reduced
from 1.5 to 1.0 ppm in 1998.[8a] Considering the diffi-
culty in acquiring the fluoride anion chemsensor, we
expect that the PN-Fe chemsensor might be a latent
sensor material for F‾ detection.
[7] (a) Mohapatra, S.; Sahu, S.; Nayak, S.; Ghosh, S. K. Langmuir 2015,
31, 8111; (b) Sui, B.; Kim, B.; Zhang, Y.; Frazer, A.; Belfield, K. D.
ACS Appl. Mater. Interfaces 2013, 5, 2920.
[8] (a) Ayoob, S.; Gupta, A. K. Crit. Rev. Env. Sci. Technol. 2006, 36,
433; (b) Singh, P. P.; Barjatiya, M. K.; Dhing, S.; Bhatnagar, R.;
Kothari, S.; Dhar, V. Urol. Res. 2001, 29, 238; (c) WHO (World
Health Organization), Guidelines for Drinking Water Quality, World
Health Organization, Geneva, 1985, Vol. 3, pp. 1-2; (d) WHO
(World Health Organization), Guideline for Drinking Water Quality
Health Criteria and Other Supporting Information, World Health
Organization, Geneva, 2nd edn, 1997, Vol. 2.
[9] (a) Qu, Y.; Hua, J.; Tian, H. Org. Lett. 2010, 12, 3320; (b) Kim, T. H.;
Swager, T. M. Angew. Chem., Int. Ed. 2003, 42, 4803; (c) Zhao, Q.;
Li, F.; Huang, C. Chem. Soc. Rev. 2010, 39, 3007; (d) Lee, A.; You,
R.; Choi, W.; Jo, Y.; Kim, R.; Noh, I.; Kim, J.; Kim, Y.; Kim, C .
Dalton Trans. 2014, 43, 6650.
Acknowledgement
This work was supported by the National Natural
Science Foundation of China (Nos. 21161018,
21262032, 21574104) and the Program for Chang Jiang
Scholars and Innovative Research Team in University of
Ministry of Education of China (No. IRT1177).
References
[10] (a) Santra, M.; Roy, B.; Ahn, K. H. Org. Lett. 2011, 13, 3422; (b)
Hang, Y.; Li, W.; Wang, Q.; Zhang, R.; Xiong, Q.; Shen, X.; Guo, J.;
Chen, X. Acta Chim. Sinica 2013, 71, 1496 (in Chinese); (c) Wu, G.;
Shi, B.; Hu, B.; Zhng, Y.; Lin, Q.; Yao, H.; Wei, T. Chin. J. Chem.
2014, 32, 637.
[11] (a) Lin, Q.; Zhu, X.; Fu, Y.; Yang, Q.; Sun, B.; Wei, T.; Zhang, Y.
Dyes Pigments 2015, 113, 748; (b) Gao, G.; Qu, W.; Shi, B.; Lin, Q.;
Yao, H.; Zhang, Y.; Chang, J.; Cai, Y.; Wei, T. Sens. Actuators B
2015, 213, 501; (c) Qu, W.; Gao, G.; Shi, B.; Wei, T.; Zhang, Y.; Lin,
Q.; Yao, H. Sens. Actuators B: Chem. 2014, 204, 368; (d) Yao, H.;
You, X.; Lin, Q.; Wu, H.; Wei, T.; Zhang, Y. Chin. J. Chem. 2014, 32,
607; (e) Shi, B.; Zhang, P.; Wei, T.; Yao, H.; Lin, Q. ; Zhang, Y.
Chem. Commun. 2013, 49, 7812; (f) Zhang, Y.; Lin, Q.; Wei, T.;
Wang, D.; Yao, H.; Wang, Y. Sens. Actuators B 2009, 137, 447; (g)
Zhang, Y.; Lin, Q.; Wei, T.; Qin, X.; Li, Y. Chem. Commun. 2009,
6074.
[1] Tomoki, O.; Suguru, K.; Shuhei, F.; Tada-aki, Y.; Yoshiaki, N. J. Am.
Chem. Soc. 2008, 130, 5022.
[2] (a) Zayed, J. M.; Nouvel, N.; Rauwald, U.; Scherman, O. A. Chem.
Soc. Rev. 2010, 39, 2806; (b) Wu, X.; Gao, L.; Hu, X. Y.; Wang, L.
Chem. Rec. 2016, 16, 1216; (c) Li, C. Chem. Commun. 2014, 50,
12420.
[3] (a) Tomoki, O.; Suguru, K.; Shuhei, F.; Tada-aki, Y.; Yoshiaki, N. J.
Am. Chem. Soc. 2008, 130, 5022; (b) Strutt, N. L.; Fairen-Jimenez,
D.; Iehl, J.; Lalonde, M. B.; Snurr, R. Q.; Farha, O. K.; Stoddart, J. F.
J. Am. Chem. Soc. 2012, 134, 17436; (c) Ding, C.; Liu, Y.; Wang, T.;
Fu, J. J. Mater. Chem. B 2016, 4, 2819; (d) Wang, Y.; Ping, G.; Li, C.
Chem. Commun. 2016, 52, 9858; (e) Zhang, C.; Chen, L.; Yang, H.
Chin. J. Chem. 2015, 33, 319; (f) Wang, W.; Sun, B.; Wang, X.; Ren,
Y.; Chen, L.; Ma, J.; Zhang, Y.; Li, X.; Yu, Y.; Tan, H.; Yang, H.
Chem. Eur. J. 2015, 21, 6286; (j) Li, Z.; Zhang, Y.; Zhang, C.; Chen,
L.; Wang, C.; Tan, H.; Yang, H. J. Am. Chem. Soc. 2014, 136, 8577.
[4] (a) Shi, B.; Jie, K.; Zhou, Y.; Xia, D.; Yao, Y. Chem. Commun. 2015,
51, 4503; (b) Zhou, T.; Song, N.; Yu, H.; Yang, Y. Langmuir 2015,
31, 1454; (c) Yu, G.; Ma, Y.; Han, C.; Yao, Y.; Tang, G.; Mao, Z.;
Huang, F. J. Am. Chem. Soc. 2013, 135, 10310; (d) Hong, M.; Zhang,
[12] (a) Cao, M.; Hao, Y.; Xu, Z.; Liu, S.; Yin, J. Curr. Org. Chem. 2016,
20, 1299; (b) Zhang, Z.; Yu, G.; Han, C.; Liu, C.; Ding, X.; Yu, Y.;
Huang, F. Org. Lett. 2011, 13, 4818.
[13] Analytical Methods Committee, Analyst 1987, 112, 199.
(Lu, Y.)
Chin. J. Chem. 2016, 34, 1263—1267
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