European Journal of Chemistry

An imidazole based colorimetric sensor for fluoride anion



Main Article Content

Shyamaprosad Goswami
Rinku Chakrabarty

Abstract

Nine 2,3,5-triphenylimidazole derivatives having nitro and/or OH groups at their phenyl groups as receptors have been designed and synthesized for the colorimetric detection of F- ion, among which receptor (1) having a nitro group at the para position of the 2-phenyl group with respect to the imidazole moiety shows colorimetric responses (yellow to red) in acetonitrile-water (9:1, v:v) mixture towards F- anion selectively among other anions studied. Here nitro group acts as a signaling unit and OH and NH of imidazole moieties act as binding sites respectively.


2_3_410_415_800

 


icon graph This Abstract was viewed 2869 times | icon graph Article PDF downloaded 1123 times icon graph Article SUPPLEMENTARY FILE downloaded 0 times

How to Cite
(1)
Goswami, S.; Chakrabarty, R. An Imidazole Based Colorimetric Sensor for Fluoride Anion. Eur. J. Chem. 2011, 2, 410-415.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Sohn, H.; Letant, S.; Sailor, M. J.; Trogler, W. C. J. Am. Chem. Soc. 2000, 122, 5399-5400.
http://dx.doi.org/10.1021/ja0006200

[2]. Kirk, K. L. Biochemistry of Halogens and Inorganic Halides, Plenum Press: New York, 1991, pp. 58.

[3]. Bianchi, E.; Bowman, J. K.; Garcia-Espana, E. Supramolecular Chemistry of Anions, Eds.; Wiley-VCH: New York, 1997.

[4]. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419-4476.
http://dx.doi.org/10.1021/cr010421e
PMid:14611267

[5]. Lee, S. H.; Kim, H. J.; Lee, Y. O.; Vicens, J.; Kim, J. S. Tetrahedron Lett. 2006, 47, 4373-4376.
http://dx.doi.org/10.1016/j.tetlet.2006.04.093

[6]. Causey, C. P.; Allen, W. E. J. Org. Chem. 2002, 67, 5963-5968.
http://dx.doi.org/10.1021/jo020098v
PMid:12182629

[7]. Gomez, D.; Fabrizzi, L.; Licchelli, M. J. Org. Chem. 2005, 70, 5717-5720.
http://dx.doi.org/10.1021/jo050528s
PMid:15989358

[8]. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369-370.
http://dx.doi.org/10.1021/ja00054a066

[9]. Cho, E. J.; Ryu, B. J.; Lee, Y. J.; Nam, K. C. Org. Lett. 2005, 7, 2607-2609.
http://dx.doi.org/10.1021/ol0507470
PMid:15957902

[10]. Lee, D. H.; Lee, H. Y.; Hong, J. -I. Tetrahedron Lett. 2002, 43, 7273-7276.
http://dx.doi.org/10.1016/S0040-4039(02)01455-7

[11]. Best, M. D.; Tobey, S. L.; Anslyn, E. V. Coord. Chem. Rev. 2003, 240, 3-15.
http://dx.doi.org/10.1016/S0010-8545(02)00256-4

[12]. Linares, J. M.; Powell, D.; Bowman-James, K. Coord. Chem. Rev. 2003, 240, 57-75.
http://dx.doi.org/10.1016/S0010-8545(03)00019-5

[13]. In, S.; Cho, S. J.; Lee, K. H.; Kang, J. Org. Lett. 2005, 7, 3993-3996.
http://dx.doi.org/10.1021/ol0515309
PMid:16119950

[14]. Jentsch, T. Curr. Opin. Neurobiol. 1996, 6, 303-310.
http://dx.doi.org/10.1016/S0959-4388(96)80112-7

[15]. Wiseman, A. Handbook of Experimental pharmacology XX/2, Part 2; Springer-Verlag: Berlin, 1970; pp. 48.

[16]. Weatherall, J. A. Pharmacology of Fluorides. In Handbook of Experimental pharmacology XX/2, Part 2; Springer-Verlag: Berlin, 1969, pp. 141.

[17]. Dreisbuch, R. H. Handbook of Poisoning; Lange Medical Publishers: Los Altos, CA, 1980.

[18]. Sohn, H.; Letant, S.; Sailor, M. J.; Trogler, W. C. J. Am. Chem. Soc. 2000, 122, 5399-5400.
http://dx.doi.org/10.1021/ja0006200

[19]. Varner, J. A.; Jensen, K. F.; Horvath, W.; Isaacson, R. L. Brain Res. 1998, 784, 284-298.
http://dx.doi.org/10.1016/S0006-8993(97)01336-X

[20]. Duke, R. M.; Gunnlaugsson, T. Tetrahedron Lett. 2007, 48, 8043-8047.
http://dx.doi.org/10.1016/j.tetlet.2007.09.026

[21]. Chetia, B.; Iyer, P. K. Tetrahedron Lett. 2008, 49, 94-97
http://dx.doi.org/10.1016/j.tetlet.2007.11.011

[22]. Garg, B.; Bhist, T. B.; Chauhan, S. M. S. New J. Chem. 2010, 34, 1251-1254.
http://dx.doi.org/10.1039/c0nj00315h

[23]. Minami, T.; Kaneko, K.; Nagasaki, T.; Kubo, Y. Tetrahedron Lett. 2008, 49, 432-436.
http://dx.doi.org/10.1016/j.tetlet.2007.11.120

[24]. Bhosale, S. V.; Bhosale, S. V.; Kalyankar, M. B.; Langford, S. J. Org. Lett. 2009, 11, 5418-5421.
http://dx.doi.org/10.1021/ol9022722
PMid:19943698

[25]. He, X.; Hu, K.; Liu, K.; Guo, Y.; Xu, J.; Shao, S. Org. Lett. 2006, 8, 333-336.
http://dx.doi.org/10.1021/ol052770r
PMid:16408908

[26]. Anzenbacher, P. M.; Palacios, A.; Jursikova, K.; Marquez, M. Org. Lett. 2005, 7, 5027-5030.
http://dx.doi.org/10.1021/ol051992m
PMid:16235949

[27]. Kim, S. K.; Bok, J. H.; Bartsch, R. A.; Lee, J. Y.; Kim, J. S. Org. Lett. 2005, 7, 4839-4842.
http://dx.doi.org/10.1021/ol051609d
PMid:16235902

[28]. Kumar, S.; Luxami, V.; Kumar, A. Org. Lett. 2008, 10, 5549-5552.
http://dx.doi.org/10.1021/ol802352j
PMid:19032039

[29]. Lu, Q.-S.; Dong, L.; Zhang, J.; Li, J.; Jiang, L.; Huang, Y.; Qin, S.; Hu, C.-W.; Yu, X.-Q. Org. Lett. 2009, 11, 669-672.
http://dx.doi.org/10.1021/ol8027303
PMid:19143512

[30]. Saravanakumar, D.; Devaraj, S.; Iyyampillai, S.; Mohandoss, K.; Kandaswamy, M. Tetrahedron Lett. 2008, 49, 127-132.
http://dx.doi.org/10.1016/j.tetlet.2007.11.006

[31]. Cho, E. J.; Ryu, B. J.; Lee, Y. J.; Nam, K. C. Org. Lett. 2005, 7, 2607-2609.
http://dx.doi.org/10.1021/ol0507470
PMid:15957902

[32]. Yu, M.; Lin, H.; Zhao, G.; Lin, H. J. Mol. Recog. 2007, 1, 69-73.
http://dx.doi.org/10.1002/jmr.810
PMid:17117448

[33]. Caltagirone, C.; Gale, P. A., Chem. Soc. Rev. 2009, 38, 520-563.
http://dx.doi.org/10.1039/b806422a
PMid:19169465

[34]. Han, F.; Bao, Y.; Yang, Z.; Fyles, T. M.; Zhao, J.; Peng, X.; Fan, J.; Wu, Y.; Sun, S. Chem. Eur. J. 2007, 13, 287-291.
http://dx.doi.org/10.1002/chem.200600557
PMid:17004290

[35]. Zhang, M.; Li, M.; Li, F.; Cheng, Y.; Zhang, J.; Yi, T.; Huang, C. Dyes and Pigments 2008, 77, 408-414.
http://dx.doi.org/10.1016/j.dyepig.2007.07.003

[36]. Cao, D.; Liu, Z.; Li, G. Sensors and Actuators B: Chemical 2008, 133, 489-492.
http://dx.doi.org/10.1016/j.snb.2008.03.006

[37]. Xu, Z. W.; Tang, J.; Tian, H. Chinese Chem. Lett. 2008, 19, 1353-1357.
http://dx.doi.org/10.1016/j.cclet.2008.09.005

[38]. Mashraqui, S. H.; Betkar, R.; Chandiramani, M.; Quinonero, D.; Frontera, A. Tetrahedron Lett. 2010, 51, 596-599.
http://dx.doi.org/10.1016/j.tetlet.2009.11.050

[39]. Zhou, J. L.; Zhang, X. H.; Wu, S. K. Sensors Actuat. B-Chem. 2005, 106, 343-346.

[40]. Luxami, V.; Kumar, S. Tetrahedron Lett. 2007, 48, 3083-3087.
http://dx.doi.org/10.1016/j.tetlet.2007.02.095

[41]. Bhardwaj, V. K.; Hundal, M. S.; Hundal, G. Tetrahedron 2009, 65, 8556-8562.
http://dx.doi.org/10.1016/j.tet.2009.08.023

[42]. Wade, C. R.; Broomsgrove, A. E. J.; Aldridge, S.; Gabba, F. P. Chem. Rev. 2010, 110, 3958-3984.
http://dx.doi.org/10.1021/cr900401a
PMid:20540560

[43]. Zhao, C.-H.; Sakuda, E.; Wakamiya, A.; Yamaguchi, S. Chem. Eur. J. 2009, 15, 10603-10612.
http://dx.doi.org/10.1002/chem.200900864
PMid:19739210

[44]. Batista, R. M. F.; Oliveira, E.; Costa, S. P. G.; Lodeiro, C.; Raposo, M. M. M. Org. Lett. 2007, 9, 32013204.
http://dx.doi.org/10.1021/ol071029b
PMid:17645345

[45]. Neumann, T.; Dienes, Y.; Baumgartner, T. Org. Lett, 2006, 8, 495-497.
http://dx.doi.org/10.1021/ol052911p
PMid:16435868

[46]. Day, J. K.; Bresner, C.; Coombs, N. D.; Fallis, I. A.; Ooi, L.-L.; Aldridge, S. Inorg. Chem. 2008, 47, 793-804.
http://dx.doi.org/10.1021/ic701494p
PMid:17929916

[47]. Saravanakumar, D.; Sengottuvelan, N.; Kandaswamy, M.; Aravindan, P. G.; Velmurugan, D. Tetrahedron Lett. 2005, 46, 7255-7258.
http://dx.doi.org/10.1016/j.tetlet.2005.08.045

[48]. Shiraishi, Y.; Maehara, H.; Hirai, T. Org. Biomol. Chem. 2009, 7, 2072-2076.
http://dx.doi.org/10.1039/b821466b

[49]. Hudnall, T. W.; Gabbai, F. P. Chem. Commun. 2008, 4586-4587.

[50]. Cecon, L. A.; Coraor, G. R.; Dessauer, R.; Silversmith, E. F.; Urban, E. J. J. Org. Chem. 1971, 36, 2262-2267.
http://dx.doi.org/10.1021/jo00815a014

[51]. Camiolo, S.; Gale, P. A.; Hursthouse, M. B.; Light, M. E. Org. Biomol. Chem. 2003, 1, 741-744.
http://dx.doi.org/10.1039/b210848h

[52]. Benesi, H.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703-2707.
http://dx.doi.org/10.1021/ja01176a030

[53]. Yuan, M.; Li, Y.; Li, J.; Li, C.; Liu, X.; Lv. J.; Xu, J.; Liu, H.; Wang, S.; Zhu, D. Org. Lett. 2007, 9, 2313-2316.
http://dx.doi.org/10.1021/ol0706399
PMid:17474750

[54]. Yang, C.; Liu, L.; Mu, T. -W.; Guo, Q. -X. Anal. Sci. 2000, 16, 537-539.
http://dx.doi.org/10.2116/analsci.16.537

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).