European Journal of Chemistry 2011, 2(3), 410-415 | doi: https://doi.org/10.5155/eurjchem.2.3.410-415.189 | Get rights and content

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An imidazole based colorimetric sensor for fluoride anion


Shyamaprosad Goswami (1,*) , Rinku Chakrabarty (2)

(1) Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah-711103, India
(2) Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah-711103, India
(*) Corresponding Author

Received: 29 Jun 2010 | Revised: 13 Sep 2010 | Accepted: 15 Dec 2010 | Published: 30 Sep 2011 | Issue Date: September 2011

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

 


Keywords


Anion recognition; Colorimetric; Fluorescent; Fluoride; Imidazole based receptor; Steric hindrance

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DOI: 10.5155/eurjchem.2.3.410-415.189

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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 information


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Goswami, S.; Chakrabarty, R. Eur. J. Chem. 2011, 2(3), 410-415. doi:10.5155/eurjchem.2.3.410-415.189
Goswami, S.; Chakrabarty, R. An imidazole based colorimetric sensor for fluoride anion. Eur. J. Chem. 2011, 2(3), 410-415. doi:10.5155/eurjchem.2.3.410-415.189
Goswami, S., & Chakrabarty, R. (2011). An imidazole based colorimetric sensor for fluoride anion. European Journal of Chemistry, 2(3), 410-415. doi:10.5155/eurjchem.2.3.410-415.189
Goswami, Shyamaprosad, & Rinku Chakrabarty. "An imidazole based colorimetric sensor for fluoride anion." European Journal of Chemistry [Online], 2.3 (2011): 410-415. Web. 18 Aug. 2022
Goswami, Shyamaprosad, AND Chakrabarty, Rinku. "An imidazole based colorimetric sensor for fluoride anion" European Journal of Chemistry [Online], Volume 2 Number 3 (30 September 2011)

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