Abstract
Acylhydrazone derivatives N′-[1-(2-fluorophenyl)ethylidene]pyridine-3-carbohydrazide (R1) and N′-[2-fluorobenzylidene]benzohydrazide (R2) were synthesized from their corresponding hydrazides and characterized by spectroscopic methods. The response of these acylhydrazones towards different anions was studied by colorimetric and spectrofluorometric methods in acetonitrile. The receptors exhibited a specific response towards fluoride ion. The binding affinity of the receptors with fluoride anion was studied by fluorescence spectroscopic techniques and ab initio density functional theory calculations with Becker’s three-parameter Lee–Yang–Par (B3LYP) exchange functional with 6-311G basis set.
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Y. Zhou, Z. Xu, J. Yoon, Chem. Soc. Rev. 40, 2222 (2011)
H.N. Kim, W.X. Ren, J.S. Kim, J. Yoon, Chem. Soc. Rev. 41, 3210 (2012)
Y. Zhou, J. Yoon, Chem. Soc. Rev. 41, 52 (2012)
J. Jose, R. Datta, P.B. Sreeja, Orient. J. Chem. 33, 1438 (2017)
H.T. Chifotides, B.L. Schottel, K.R. Dunbar, Acc. Chem. Res. 46, 894 (2013)
V. Baelum, S. Pongpaisal, W. Pithpornchaiyakul, S. Pisuithanakan, R. Teanpaisan, P.N. Papapanou, G. Dahlen, O. Fejerskov, Acta Odontol. Scand. 60, 80 (2002)
S. Purser, P.R. Moore, D.O. Hagan, S. Purser, P.R. Moore, Chem. Soc. Rev. 37, 320 (2008)
A. Strunecka, P. Connett, J. Appl. Biomed. 2, 141 (2004)
H. Rosenberg, J.C. Mosteller, W. Air, W.A.F. Base, O.F.W. Spray, Ind. Eng. Chem. 45, 2283 (1953)
Z. Liang, W. Limin, Z. Guanjun, Y. Jianjun, C. Xiaofei, T. Mingshuang, W. Yue, Chin. J. Chem. 30, 2823 (2012)
Y. Qu, J. Hua, H. Tian, Chem. Soc. Rev. 39, 3007 (2010)
D.A. Jose, D.K. Kumar, B. Ganguly, A. Das, Org. Lett. 6, 3445 (2004)
P.D. Beer, P.A. Gale, Angew. Chem. Int. Ed. 40, 486 (2001)
P.A. Gale, Coordin. Chem. Rev. 240, 191 (2003)
V. Amendola, D. Esteban-go, Ä. Mez, L. Fabbrizzi, M. Licchelli, C. Generale, Acc. Chem. Res. 39, 343 (2006)
P.A. Gale, R. Quesada, Coord. Chem. Rev. 250, 3219 (2006)
V.K. Gupta, R.N. Goyal, R.A. Sharma, Talanta 76, 859 (2008)
P.B. Sreeja, M. Sithambaresan, N. Aiswarya, M.R.P. Kurup, Acta Crystallogr. E 70, o115 (2014)
P.B. Sreeja, M. Sithambaresan, N. Aiswarya, M.R.P. Kurup, Acta Crystallogr. E 70, o532 (2014)
P.B. Sreeja, M. Sithambaresan, N. Aiswarya, M.R.P. Kurup, Acta Crystallogr. E 69, o1828 (2013)
A. Saeed, S. Ashraf, J.M. White, D.B. Soria, C.A. Franca, M.F. Erben, Spectrochim. Acta Part A 150, 409 (2015)
I. Arshad, J. Yameen, A. Saeed, J. White, F. Albericio, Crystals 7, 19 (2017)
P.B. Sreeja, A. Sreekanth, C.R. Nayar, M.R.P. Kurup, A. Usman, I.A. Razak, S. Chantrapromma, H.K. Fun, J. Mol. Struct. 645, 221 (2003)
P.B. Sreeja, M.R.P. Kurup, A. Kishore, C. Jasmin, Polyhedron 23, 575 (2004)
P.B. Sreeja, M.R.P. Kurup, Spectrochim. Acta Part A 61, 331 (2005)
T. Yanai, D.P. Tew, N.C. Handy, Chem. Phys. Lett. 393, 51 (2008)
I. Yilmaz, A. Cukurovali, Dyes Pigm. 83, 211 (2009)
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P.B.S. is grateful for financial support from CHRIST (Deemed to be University), Bengaluru.
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Jose, J., Sreekanth, A., John, A.M. et al. Spectrochemical and theoretical approaches for acylhydrazone-based fluoride sensors. Res Chem Intermed 45, 425–435 (2019). https://doi.org/10.1007/s11164-018-3609-4
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DOI: https://doi.org/10.1007/s11164-018-3609-4