Table of Contents
International Journal of Inorganic Chemistry
Volume 2011, Article ID 154326, 8 pages
http://dx.doi.org/10.1155/2011/154326
Research Article

Spectral, NLO, Fluorescence, and Biological Activity of Knoevenagel Condensate of -Diketone Ligands and Their Metal(II) Complexes

1Department of Chemistry, Thiagarajar College, Madurai 625 009, India
2Department of Chemistry, The American College, Madurai 625 002, India

Received 21 November 2011; Revised 18 December 2011; Accepted 18 December 2011

Academic Editor: Wolfgang Linert

Copyright © 2011 S. Sumathi et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. G. Aromí, P. Gamez, and J. Reedijk, “Poly beta-diketones: prime ligands to generate supramolecular metalloclusters,” Coordination Chemistry Reviews, vol. 252, no. 8-9, pp. 964–989, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. T. Jeewoth, M. G. Bhowon, and H. L. K. Wah, “Synthesis, characterization and antibacterial properties of Schiff bases and Schiff base metal complexes derived from 2,3-diaminopyridine,” Transition Metal Chemistry, vol. 24, no. 4, pp. 445–448, 1999. View at Google Scholar · View at Scopus
  3. P. S. Desai and K. R. Desai, “Synthesis and antibacterial activity of 2-(6′-chlorobenzothiazol-2′-ylamino)-4-N4-N1-(n-butyl)sulphanilamido-6-(arylthioureido)-s-triazine derivatives,” Journal of the Indian Chemical Society, vol. 70, pp. 177–178, 1993. View at Google Scholar
  4. J. Lv, T. Liu, S. Cai, X. Wang, L. Liu, and Y. Wang, “Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived schiff bases,” Journal of Inorganic Biochemistry, vol. 100, no. 11, pp. 1888–1896, 2006. View at Publisher · View at Google Scholar · View at Scopus
  5. R. Del Campo, J. J. Criado, E. García et al., “Thiourea derivatives and their nickel(II) and platinum(II) complexes: antifungal activity,” Journal of Inorganic Biochemistry, vol. 89, no. 1-2, pp. 74–82, 2002. View at Publisher · View at Google Scholar
  6. S. Belaid, A. Landreau, S. Djebbar, O. Benali-Baitich, G. Bouet, and J. P. Bouchara, “Synthesis, characterization and antifungal activity of a series of manganese(II) and copper(II) complexes with ligands derived from reduced N,N′-O-phenylenebis(salicylideneimine),” Journal of Inorganic Biochemistry, vol. 102, no. 1, pp. 63–69, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. Y. Liu, J. Zhou, X. Zhang et al., “Synthesis, characterization and optical limiting property of covalently oligothiophene-functionalized graphene material,” Carbon, vol. 47, no. 13, pp. 3113–3121, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. K. Sendhil, C. Vijayan, and M. P. Kothiyal, “Nonlinear optical properties of a porphyrin derivative incorporated in Nafion polymer,” Optical Materials, vol. 27, no. 10, pp. 1606–1609, 2005. View at Publisher · View at Google Scholar · View at Scopus
  9. N. Tsuboya, R. Hamasaki, M. Ito, M. Mitsuishi, T. Miyashita, and Y. Yamamoto, “Nonlinear optical properties of novel fullerene-ferrocene hybrid molecules,” Journal of Materials Chemistry, vol. 13, no. 3, pp. 511–513, 2003. View at Publisher · View at Google Scholar · View at Scopus
  10. M. N. Bhat and S. M. Dharmaprakash, “Effect of solvents on the growth morphology and physical characteristics of nonlinear optical γ-glycine crystals,” Journal of Crystal Growth, vol. 242, no. 1-2, pp. 245–252, 2002. View at Publisher · View at Google Scholar · View at Scopus
  11. P. Nandakumar, C. Vijayan, and Y. V. G. S. Murti, “Optical absorption and photoluminescence studies on CdS quantum dots in Nafion,” Journal of Applied Physics, vol. 91, no. 3, pp. 1509–1514, 2002. View at Publisher · View at Google Scholar · View at Scopus
  12. T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, and A. Persoons, “Second-order nonlinear optical materials: recent advances in chromophore design,” Journal of Materials Chemistry, vol. 7, no. 11, pp. 2175–2189, 1997. View at Google Scholar · View at Scopus
  13. Y. Zhang, H. Li, B. Xi, Y. Che, and J. Zheng, “Growth and characterization of l-histidine nitrate single crystal, a promising semiorganic NLO material,” Materials Chemistry and Physics, vol. 108, no. 2-3, pp. 192–195, 2008. View at Publisher · View at Google Scholar · View at Scopus
  14. S. Sumathi, P. Tharmaraj, C. D. Sheela, and R. Ebenezer, “Synthesis, spectral, bioactivity, and NLO properties of chalcone metal complexes,” Journal of Coordination Chemistry, vol. 64, no. 10, pp. 1707–1717, 2011. View at Publisher · View at Google Scholar
  15. S. Sumathi, P. Tharmaraj, C. D. Sheela, R. Ebenezer, and P. Saravana Bhava, “Synthesis, characterization, NLO study, and antimicrobial activities of metal complexes derived from 3-(3-(2-hydroxyphenyl)-3-oxoprop-1-enyl)-4H- chromen-4-one and sulfanilamide,” Journal of Coordination Chemistry, vol. 64, no. 10, pp. 1673–1682, 2011. View at Publisher · View at Google Scholar
  16. S. Srinivasan, P. Athappan, and G. Rajagopal, “Synthesis, spectral and redox properties of metal complexes of macrocyclic tetraaza chiral Schiff bases,” Transition Metal Chemistry, vol. 26, no. 4-5, pp. 588–593, 2001. View at Publisher · View at Google Scholar · View at Scopus
  17. A. P. Zambre, V. M. Kulkarni, S. Padhye, S. K. Sandur, and B. B. Aggarwal, “Novel curcumin analogs targeting TNF-induced NF-κB activation and proliferation in human leukemic KBM-5 cells,” Bioorganic and Medicinal Chemistry, vol. 14, no. 21, pp. 7196–7204, 2006. View at Publisher · View at Google Scholar · View at Scopus
  18. N. Raman, R. Jeyamurugan, R. U. Rani, T. Baskaran, and L. Mitu, “Synthesis, characterization, DNA binding, oxidative damage of DNA strand scission, and antimicrobial activities of β-diketone condensed Schiff-base transition metal complexes,” Journal of Coordination Chemistry, vol. 63, no. 9, pp. 1629–1644, 2010. View at Publisher · View at Google Scholar · View at Scopus
  19. S. K. Kurtz and T. T. Perry, “A powder technique for the evaluation of nonlinear optical materials,” Journal of Applied Physics, vol. 39, no. 8, pp. 3798–3813, 1968. View at Publisher · View at Google Scholar · View at Scopus
  20. O. N. Irobi, M. Moo-Young, and W. A. Anderson, “Antimicrobial activity of Annatto (Bixa orellana) extract,” International Journal of Pharmacognosy, vol. 34, no. 2, pp. 87–90, 1996. View at Google Scholar · View at Scopus
  21. J. P. Annaraj, K. M. Ponvel, P. Athappan, and S. Srinivasan, “Synthesis, spectra and redox behavior of copper(II) complexes of curcumin diketimines as models for blue copper proteins,” Transition Metal Chemistry, vol. 29, no. 7, pp. 722–727, 2004. View at Publisher · View at Google Scholar · View at Scopus
  22. A. Kulkarni, P. G. Avaji, G. B. Bagihalli, S. A. Patil, and P. S. Badami, “Synthesis, spectral, electrochemical and biological studies of Co(II), Ni(II) and Cu(II) complexes with Schiff bases of 8-formyl-7-hydroxy-4-methyl coumarin,” Journal of Coordination Chemistry, vol. 62, no. 3, pp. 481–492, 2009. View at Publisher · View at Google Scholar · View at Scopus
  23. A. Veeraraj, P. Sami, and N. Raman, “Copper(II) complex of 3-cinnamalideneacetylacetone: synthesis and characterisation,” Proceedings of the Indian Academy of Sciences: Chemical Sciences, vol. 112, no. 5, pp. 515–521, 2000. View at Google Scholar · View at Scopus
  24. M. Kalanithi, D. Kodimunthiri, M. Rajarajan, and P. Tharmaraj, “Synthesis, characterization and biological activity of some new VO(IV), Co(II), Ni(II), Cu(II) and Zn(II) complexes of chromone based NNO Schiff base derived from 2-aminothiazole,” Spectrochimica Acta A, vol. 82, no. 1, pp. 290–298, 2011. View at Publisher · View at Google Scholar
  25. K. Z. Ismail, “Synthesis, spectroscopic, magnetic and biological activity studies of copper(II) complexes of an antipyrine Schiff base,” Transition Metal Chemistry, vol. 25, no. 5, pp. 522–528, 2000. View at Publisher · View at Google Scholar · View at Scopus
  26. F. A. Cotton, G. Wilkinson, C. A. Murillo, and M. Bochmann, Advanced Inorganic Chemistry, Wiley, New York, NY, USA, 6th edition, 1999.
  27. M. M. Omar and G. G. Mohamed, “Potentiometric, spectroscopic and thermal studies on the metal chelates of 1-(2-thiazolylazo)-2-naphthalenol,” Spectrochimica Acta A, vol. 61, no. 5, pp. 929–936, 2005. View at Publisher · View at Google Scholar · View at Scopus
  28. K. Y. El-Baradie, “Preparation and characterization of sulfadiazine Schiff base complexes of Co(II), Ni(II), Cu(II), and Mn(II),” Monatshefte fur Chemie, vol. 136, no. 7, pp. 1139–1155, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. Y. S. Rao, B. Prathima, S. A. Reddy, K. Madhavi, and A. V. Reddy, “Complexes of Cu(II) and Ni(II) with bis(phenylthiosemicarbazone): synthesis, spectral, EPR and in vitro—antibacterial and antioxidant activity,” Journal of the Chinese Chemical Society, vol. 57, no. 4, pp. 677–682, 2010. View at Google Scholar · View at Scopus
  30. G. G. Mohamed and C. M. Sharaby, “Metal complexes of Schiff base derived from sulphametrole and o-vanilin. Synthesis, spectral, thermal characterization and biological activity,” Spectrochimica Acta A, vol. 66, no. 4-5, pp. 949–958, 2007. View at Publisher · View at Google Scholar · View at Scopus
  31. C. M. Sharaby, “Preparation, characterization and biological activity of Fe(III), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and UO2(II) complexes of new cyclodiphosph(V)azane of sulfaguanidine,” Spectrochimica Acta A, vol. 62, no. 1–3, pp. 326–334, 2005. View at Publisher · View at Google Scholar · View at Scopus
  32. M. Vaidyanathan, R. Viswanathan, M. Palaniandavar, T. Balasubramanian, P. Prabhaharan, and T. P. Muthiah, “Copper(II) complexes with unusual axial phenolate coordination as structural models for the active site in galactose oxidase: X-ray crystal structures and spectral and redox properties of [Cu(bpnp)X] complexes,” Inorganic Chemistry, vol. 37, no. 25, pp. 6418–6427, 1998. View at Google Scholar · View at Scopus
  33. R. Karvembu and K. Natarajan, “Synthesis and spectral studies of binuclear ruthenium(II) carbonyl complexes containing bis(β-diketone) and their applications,” Polyhedron, vol. 21, no. 2, pp. 219–223, 2002. View at Publisher · View at Google Scholar · View at Scopus
  34. P. S. Mane, S. G. Shirodkar, and T. K. Chondhekar, “Synthesis of complexes of copper(II), nickel(II), cobalt(II), manganese(II) and iron(III) with bidentate Schiff bases,” Journal of the Indian Chemical Society, vol. 79, no. 4, pp. 376–378, 2002. View at Google Scholar · View at Scopus
  35. J. Joseph and B. H. Mehta, “Synthesis, characterization, and thermal analysis of transition metal complexes of polydentate ONO donor Schiff base ligand,” Russian Journal of Coordination Chemistry, vol. 33, no. 2, pp. 124–129, 2007. View at Publisher · View at Google Scholar · View at Scopus
  36. S. A. Sallam, A. S. Orabi, B. A. El-Shetary, and A. Lentz, “Copper, nickel and cobalt complexes of Schiff-bases derived from β-diketones,” Transition Metal Chemistry, vol. 27, no. 4, pp. 447–453, 2002. View at Publisher · View at Google Scholar · View at Scopus
  37. P. Tharmaraj, D. Kodimunthiri, C. D. Sheela, and C. S. Shanmuga Priya, “Synthesis, spectral characterization, and antimicrobial activity of copper(II), cobalt(II), and nickel(II) complexes of 3-formylchromoniminopropylsilatrane,” Journal of Coordination Chemistry, vol. 62, no. 13, pp. 2220–2228, 2009. View at Publisher · View at Google Scholar · View at Scopus
  38. R. Kannappan, R. Mahalakshmy, T. M. Rajendiran, R. Venkatesan, and P. Sambasiva Rao, “Magnetic, catalytic, EPR and electrochemical studies on binuclear copper(II) complexes derived from 3,4-disubstituted phenol,” Proceedings of the Indian Academy of Sciences: Chemical Sciences, vol. 115, no. 1, pp. 1–14, 2003. View at Google Scholar · View at Scopus
  39. D. Kivelson and R. Neman, “ESR studies on the bonding in copper complexes,” The Journal of Chemical Physics, vol. 35, no. 1, pp. 149–155, 1961. View at Google Scholar · View at Scopus
  40. R. K. Ray and G. B. Kauffman, “EPR Spectra and covalency of bis(amidinourea/O-alkyl-1-amidinourea)copper(II) complexes. Part II. Properties of the CuN42- chromophore,” Inorganica Chimica Acta, vol. 173, no. 2, pp. 207–214, 1990. View at Google Scholar · View at Scopus
  41. A. Majumder, G. M. Rosair, A. Mallick, N. Chattopadhyay, and S. Mitra, “Synthesis, structures and fluorescence of nickel, zinc and cadmium complexes with the N,N,O-tridentate Schiff base N-2-pyridylmethylidene-2-hydroxy-phenylamine,” Polyhedron, vol. 25, no. 8, pp. 1753–1762, 2006. View at Publisher · View at Google Scholar · View at Scopus
  42. W. Wang, G. Springsteen, S. Gao, and B. Wang, “The first fluorescent sensor for boronic and boric acids with sensitivity at sub-micromolar concentrations,” Chemical Communications, no. 14, pp. 1283–1284, 2000. View at Google Scholar · View at Scopus
  43. N. Chattopadhyay, A. Mallick, and S. Sengupta, “Photophysical studies of 7-hydroxy-4-methyl-8- (4′-methylpiperazin-1′-yl) methylcoumarin: a new fluorescent chemosensor for zinc and nickel ions in water,” Journal of Photochemistry and Photobiology A: Chemistry, vol. 177, no. 1, pp. 55–60, 2006. View at Publisher · View at Google Scholar · View at Scopus
  44. M. Jalali-Heravi, A. A. Khandar, and I. Sheikshoaie, “Theoretical investigation of the structure, electronic properties and second-order nonlinearity of some azo Schiff base ligands and their monoanions,” Spectrochimica Acta A, vol. 55, no. 12, pp. 2537–2544, 1999. View at Publisher · View at Google Scholar · View at Scopus
  45. C. D. Sheela, C. Anitha, P. Tharmaraj, and D. Kodimunthri, “Synthesis, spectral characterization, and antimicrobial studies of metal complexes of the schiff base derived from [4-amino-N-guanylbenzene sulfonamide] and salicylaldehyde,” Journal of Coordination Chemistry, vol. 63, no. 5, pp. 884–893, 2010. View at Publisher · View at Google Scholar · View at Scopus
  46. M. Muthukumar and P. Viswanathamurthi, “Spectral, catalytic, and antifungal studies of ruthenium(II) chalcone complexes,” Journal of Coordination Chemistry, vol. 63, no. 7, pp. 1263–1272, 2010. View at Publisher · View at Google Scholar · View at Scopus
  47. N. Raman, R. Jeyamurugan, and J. Joseph, “Anti-inflammatory and antimicrobial studies of biosensitive Knoevenagel condensate β-ketoanilide Schiff base and its Co(II),Ni(II), Cu(II) and Zn(II) complexes,” Journal of the Iranian Chemical Research, vol. 3, pp. 83–95, 2010. View at Google Scholar
  48. N. Raman and J. Joseph, “Synthesis, spectral characterization and antimicrobial activity of macrocyclic Schiff-base copper(II) complexes containing polycrystalline nanosized grains,” Journal of Coordination Chemistry, vol. 62, no. 7, pp. 1162–1171, 2009. View at Publisher · View at Google Scholar · View at Scopus