Fluorescence Chemosensing of Mg2+ by Phenylhydrazone of a Difluorenylpiperidin-4-one

Document Type: Research Paper

Authors

1 Department of Chemistry, Muthayammal College of Arts and Science, Namakkal District, Tamil Nadu, India.

2 Nanotoxicology Research Lab, Department of Nanoscience, Department of Chemistry, Karunya Institute of technology and Sciences, Coimbatore, India

Abstract

Magnesium is an abundant element in the environment. Magnesium ion sensing by fluorescence spectral method is of importance due to the need for the detection of the metal in the human body and the environment. In this paper, we report the Mg2+ ion sensing behavior of the phenylhydrazone derivative of a difluorenylpiperidin-4-one. The preparation method of this compound is simple. The compound shows an enhanced absorption and fluorescence in the presence of Mg2+ ions, strikingly different from the other metal ions, which do not show significant spectral changes. The stoichiometry and the binding strength of the Mg2+ complex of the phenylhydrazone are determined. The compound shows an association constant of 3375.36 M-1 on binding to Mg2+. The range of detection and the competitive binding behavior of Mg2+ are reported. The phenylhydrazone of the difluorenylpiperidin-4-one shows appreciable selectivity and sensitivity of detection for Mg2+ ions. The compound shows promising result in determination of Mg2+ ions in water sample.

Keywords


[1]       G. Tamilselvan, M. Kumaresan, R. Sivaraj, P.M. Selvakumar, I.V.M.V. Enoch, Sens. Actuators B 229 (2016) 181.

[2]       P.R. Queen, R. Sivaraj, P.M. Selvakumar, F.G.D. Banos, G. Villora, J.P. Ceron-Carrasco, H. Perez-sanchez, I.V.M.V. Enoch, RSC Adv. 6 (2016) 15670.

[3]       E.J. Antony, R. Masilamani, P.R. Queen, P.M. Selvakumar, I.V.M.V. Enoch, J. Fluoresc. 25 (2015) 1031.

[4]       A. Hartiwig, Mutat. Res. 475 (2001) 113.

[5]       B.O. Rourke, P.H. Backx, E. Marban, Science 257 (1992) 245.

[6]       L.J. Dai, G. Ritchie, D. Kerstan, H.S. Kang, D.E.C. Cole, G.A. Quamme, Physiol. Rev. 81 (2001) 51.

[7]       D. Zhai, J. Yang, Z. Guo, Q. Wang, J. Ouyang, RSC Adv. 4 (2014) 46800. 

[8]       F.I. Wolf, A. Torsello, A. Fasanella, A. Cittadini, Mol. Asp. Med. 24 (2003) 11.

[9]       C. Schmitz, A. Perraud, C.O. Johnson, K. Inabe, M.K. Smith, R. Penner, T. Kurosaki, A. Fleig, A.M. Scharenberg, Cell 114 (2003) 191.

[10]    A.M.P. Romani, Arch. Biochem. Biophys. 512 (2011) 1.  

[11]    O.B. Stepura, A.I. Martynow, Int. J. Cardiol. 131 (2009) 293.

[12]    J.H.F. de Baaij, J.G.J. Hoenderop, R.J.M. Bindels, Physiol. Rev. 95 (2015) 1.

[13]    F.H. Nielson, H.C. Lukaski, Magnes. Res. 19 (2006) 180.

[14]    R.M. Toyuz, Front. Biosci. 1 (2004) 1278.

[15]    J. Kim, T. Morozumi, H. Nakamura, Org. Lett. 9 (2007) 4419.

[16]    Y. Liu, M. Han, H. Y. Zhang, L.X. Yang, W. Jiang, Org. Lett. 10 (2008) 2873.

[17]    G. Farruggia, S. Iotti, L. Prodi, M. Montalti, N. Zaccheroni, P.B. Savage, V. Trapani, P. Sale, F.I. Wolf, J. Am. Chem. Soc. 28 (2006) 344.

[18]    Y. Dong, J. Li, X. Jiang, F. Song, Y. Cheng, C. Zhu, Org. Lett. 13 (2011) 2252.

[19]    P.S. Hariharan, S.P. Anthony, RSC Adv. 4 (2014) 41565.

[20]    M.H. Kao, T.Y. Chen, Y.R. Cai, C.H. Hu, Y.W. Liu, Y. Jhong, A.T. Wu, J. Lumin. 169 (2016) 156.

[21]    Y. Chen, S. Wang, X. Xu, X. Lu, M. Yu, S. Zhau, S. Lu, Y. Qiu, T. Zhang, B. Lui, G. Zhang, J. Med. Chem. 56 (2013) 4671.

[22]    J. Jansssens, L. Stokbroek, J. Med. Chem. 28 (1985) 1925.

[23]    F. Mathia, S. Marchalin, D. Vegh, M. Bobosikova, M. Halinkovicova, Acta Chem. Slov. 5 (2012) 145.

[24]    J. Emile, G. Motte, M. Madeleine, M. Albert, WO 2013/160435, A1.

[25]    S. Ranjan, F. Shirazi, P. Madhukar, WO 2010/109299, A1.

[26]    M.T. Gulluioglu, Y. Erdogdu, S. Yurdakul, J. Mol. Struct. 540 (2007) 834.

[27]    J.M.C. Xavier, S. Chandrsekaran, I.V. Enoch, V. Gunasekaran, Appl. Spectrosc. 67 (2013) 1042.

[28]    H. Benesi, J. Hildebrand, J. Am. Chem. Soc. 71 (1949) 2703.

[29]    W.F. Li, H.C. Ma, C. Lu, Y. Ma, C.X. Qi, Z.W. Zhang, Z.M. Yang, H.Y. Cao, Z.A. Ley, RSC Adv. 5 (2015) 6869.

[30]    G. Li, F.R. Tao, H. Wang, Y.C. Li,  L.P.  Wang,  Sens. Actuators B 211 (2015) 325.

[31]    S. Poomalai, T.S. Govindaraj, S. Soundrapandian, M.S. Paulraj, I.V.M.V. Enoch, Luminescence 33 (2018) 538.

[32]    M.   Sumithra,    R.     Sivaraj,    G.T.    Selvan,    P.M. Selvakumar, I.V.M.V. Enoch, J. Lumin. 185 (2017) 205.

[33]    J. Zhang, B.J. Zhao, C. Li, X.F. Zhu, R.Z. Qiao, Sens. Actuators B 196 (2014) 117.