One New Azo-azomethine Derivative for Detection of Ca2+ and Cd2+ Metal Ions: Synthesis, Characterization and DFT Studies

Document Type: Research Paper

Authors

Coordination Chemistry Research Laboratory, Department of Chemistry, Faculty of Basic Science, Azarbaijan Shahid Madani University, P. O. Box: 83714-161, Tabriz, Iran

Abstract

One new azo Schiff-base derivative: 4-bromo-1,2-bis[2-hydroxy-5-(phenylazo)benzylideneamino]benzene (H2L) was synthesized and characterized by common spectroscopic techniques and elemental analysis. The ability of the new chemosensor for detection of some main and transition metal ions was studied by UV-Vis spectroscopy in the mixture of DMSO: water (9:1). Upon addition of Ca2+ and Cd2+ ions, dramatic changes were observed in the UV-Vis spectrum of ligand (one new absorbance band appeared in the range of 430- 450 nm, while the absorbance band at 351 nm disappeared). The stoichiometry of the complexes was determined using the Job method. The binding constants of Ca2+ and Cd2+ with receptor by Benesi-Hildebrand plots were found to be 2.874×104 M-1 and 6.445×104 M-1, respectively. The results indicated the receptor can recognize Ca2+ and Cd2+ ions from other cations in aqueous solution. Finally, the structure and electronic properties of the ligand and its complexes with Ca2+ and Cd2+ ions were analyzed by DFT and TD-DFT calculations.

Keywords


[1]       H. Sigel, A. Sigel, Metal Ions in Biological Systems. vol. 17: Calcium and its Role in Biology. Dekker M. New York, 1984.
[2]       M.E. Shills, Modern Nutrition in Health and Disease. 10th ed. Philadelphia: Lippincott, Williams and Wilkins, 2006.
[3]       G.A. Augustine, Curr. Opin. Neurobiol. 11 (2001) 320.
[4]       M.A. Fowler, G.L. Smith, Appl. Physiol. 107 (2009) 1981.
[5]       P. Munro, Clin J. Am. Soc. Nephrol. 5 (2010) S23.
[6]       D. Papandreou, P. Malindretos, Z. Karabouta, I. Rousso, Int. J. Endocrinol.  2010 (2009) 1.
[7]       R. Sahli, N. Raouafi, E. Maisonhautec, K. Boujlela, B. Schöllhorn, Electrochim. Acta 63 (2012) 228.
[8]       J. An, Z. Yang, M. Yan, T. Li, J. Lumin. 139 (2013) 79.
 
 
[9]       S.R. Ankireddy, J. Kim, Sens. Actuators, B 225 (2018) 3425.
[10]    E. Johna, C. Chengb, A. Bornschlegel, O. Brüggemann, T. Posnicek, M. Brandl, Sens. Actuators, B 209 (2015) 1023.
[11]    R. Velu, V.T. Ramakrishnan, P. Ramamurthy, Tetrahedron Lett. 51 (2010) 4331.
[12]     K.C. Chang, I.H. Su, G.H. Lee, W.S. Chung, Tetrahedron Lett. 48 (2007) 7274.
[13]    U. Norizaki, T. Kazuyuki, O. Akira, O. Taka-aki, Y. Hitoshi, Macromol. Symp. 186 (2002) 129.
[14]    B. Delavaux-Nicot, J. Maynadie´, D. Lavabre, S. Fery-Forgues, J. Organomet. Chem. 692 (2007) 874.
[15]    B. Delavaux-Nicot, J. Maynadie, D. Lavabre, S. Fery-Forgues, J. Organomet. Chem. 692 (2007) 3351.
[16]    E. Arunkumar, P. Chithra, A. Ajayaghosh, J. Am. Chem. Soc. 126 (2004) 6590.
[17]    E. Arunkumar, A. Ajayaghosh, J. Daub, J. Am. Chem. Soc. 127 (2005) 3156.
[18]    G. Jiang, L. Xu, S. Song, C. Zhu, Q. Wu, L. Zhang, L. Wu, Toxicology 244 (2008) 49.
[19]    R. Goyer, J. Liu, M. Waalkes, Biometals. 17 (2004) 555.
[20]    J. Godt, F. Scheidig, C. Grosse-Siestrup, V. Esche, P. Brandenburg, A. Reich, D.A. Groneberg, J. Occup. Med. Toxicol. 1 (2006) 1.
[21]    H. Parham, N. Pourreza, N. Rahbar, J. Hazard. Mater. 163 (2009) 588.
[22]    S. D’Ilio, F. Petrucci, M. D’Amato, M. Di Gregorio, O. Senofonte, N. Violante, Anal. Chim. Acta 624 (2008) 59.
[23]    M. Zougagh, A.G. Torres, J.M.C. Pavon, Talanta. 56 (2002) 753.
[24]    O. Krystofova, L. Trnkova, V. Adam, J. Zehnalek, J. Hubalek, P. Babula, R. Kizek, Sensors 10 (2010) 5308.
[25]    T. Priya, N. Dhanalakshmi, S. Thennarasu, N. Thinakaran, Carbohydr. Polym. 182 (2018) 199.
[26]    X. Liu, N. Li, M.M. Xu, C. Jiang, J. Wang, G. Song, Y. Wang, Spectrochim. Acta, Part A 208 (2019) 236.
[27]    P. Wang, D. Zhou, B. Chen, Spectrochim. Acta, Part A 207 (2019) 276.
[28]    Z.N. Lu, L. Wang, X. Zhang, Z.J. Zhu, Spectrochim. Acta, Part A 213 (2019) 57.
 
 
[29]    Y. Liu, Q. Qiao, M. Zhao, W. Yin, L. Miao, L. Wang, Z. Xu, Dyes Pigm. 133 (2016) 339.
[30]    Z. Li, S. Wang, L. Xiao, X. Li, X. Jing, X. Peng, L. Ren, Inorg. Chim. Acta 479 (2018) 148.
[31]    R. Arabahmad, Talanta 194 (2019) 119.
[32]    S. Gholizadeh Dogaheh, H. Khanmohammadi Spectrochim. Acta, Part A 179 (2017) 32.
[33]    G. Kurtoglu, B. Avar, H. Zengin, M. Kose, K. Sayin, M. Kurtoglu,  J. Mol. Liq. 200 (2014) 105.
[34]     A.K. Manna, J. Mondal, R. Chandra, K. Rout, G.K. Patra, Anal. Methods 10 (2018) 2317.
[35]    S. Banerjee, S.P. BrandãoA. Saha, RSC Adv. 6 (2016) 101924.
[36]     B. Shaabani, Z. Shaghaghi, A.A. Khandar, Spectrochim. Acta, Part A 98 (2012) 81.
[37]    Z. Shaghaghi, Spectrochim. Acta, Part A 131 (2014) 67.
[38]    Z. Shaghaghi, R. Rezanezhad, Chemistry Select. 3 (2018) 5534.
[39]    Z. Shaghaghi, G. Dehghan, Acta. Chim. Slov. 65 (2018) 670.
[40]    A.A. Khandar, Z. Rezvani, Polyhedron 18 (1999) 129.
[41]    M.J. Frisch, et al., Gaussian 09, Revision D.O1, Gaussian Inc, Wallingford CT, 2004.
[42]    C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 17 (1988) 785.
[43]    E.  Gross,  W.  Kohn,  Adv.  Quant.  Chem.  21 (1990)
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
255.
[44]    A.N. Kursunlu, E. Guler, F. Sevgi, B. Ozkalp, J. Mol. Struct. 1048 (2013) 476.
[45]    M.S.  More, S.B. Pawal, S.R. Lolage, S.S. Chavan, J. Mol. Struct. 1128 (2017) 419.
[46]    H. Galen, G. Hennrich, J.D. Mendoza, P. Prados, Eur. J. Org. Chem. (2010) 1249.
[47]    R. Arab Ahmadi, S. Amani, Molecules 17 (2012) 6434.
[48]    H. Khanmohammadi, M. Pass, K. Rezaeian, G. Talei, J. Mol. Struct. 1072 (2014) 232.
[49]    H. Khanmohammadi, A. Abdollahi, Dyes Pigm. 94 (2012) 163.
[50]    K.T. Smith, S.C. Young, G.W. DeBlasio, C.S. Hamann, J. Chem. Educ. 93 (2016) 790.
[51]    T.H. Kim, S.H. Kim, L.V. Tan, Y.G. Seo, S.Y. Park, H. Kim, J.S. Kim, Talanta 71 (2007) 1294.
[52]    Y. Dong, T.H. Kim, H.J. Kim, M.H. Lee, S.Y. Lee, R.K. Mahajan, H. Kim, J.S. Kim, J. Electroanal. Chem. 628 (2009) 119.
[53]    T.H. Kim, S.H. Kim, L.Y. Tan, Y. Dong, H. Kim, J.S. Kim, Talanta 74 (2008) 1654.
[54]    T.L. Kao, C.C. Wang, Y.T. Pan, Y.J. Shiao, J.Y. Yen, C.M. Shu, G.H.  Lee, S.M. Peng, W.S. Chung, J. Org. Chem. 70 (2005) 2912.
[55]    S.G. Niyaky, M. Montazerozohori, A. Masoudiasl, J.M. White, J. Mol. Struct. 1131 (2017) 201.