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Schiff bases of 1,5-diarylpent-4-ene-1,3-diones and their metal complexes: Synthesis, characterization and fluorescent studies

Ummathur Muhammed Basheer (Department of Chemistry, KAHM Unity Women’s College, Manjeri, Kerala, India), [email protected]
Pallikkavil Radhika (Department of Chemistry, University of Calicut, Kerala, India)
Krishnankutty Krishnannair (Department of Chemistry, University of Calicut, Kerala, India)

Four Schiff bases (H2L1 to H2L4) were synthesized by the condensation of o-aminophenol and unsaturated diketones (1,5-diarylpent-4-ene-1,3- -diones). Analytical, IR, 1H-NMR and mass spectral data revealed their existence in the imine–enamine form. Dibasic tetradentate coordination of the Schiff bases in their ML complexes (M = Cu(II), Ni(II), Co(II), Zn(II), Cd(II), and Hg(II)) was established based on physical, analytical and spectral data. The fluorescent studies of H2L4 showed that the fluorescence emission maxima shifted with increasing polarity and hydrogen bonding ability of the solvent. Paramagnetic Cu(II), Ni(II) and Co(II) ions decrease the fluorescence intensity with increasing concentration of the metal ion while diamagnetic Zn(II), Cd(II) and Hg(II) ions have very little influence on the fluorescence intensity of the Schiff base H2L4.

Keywords: o-aminophenol, imine-enamine form, tetradentate coordination, spectral data