期刊
DYES AND PIGMENTS
卷 98, 期 3, 页码 547-556出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2013.04.012
关键词
Hydrazone; Pyrrolinone; Metal-azo complex; Absorption spectra; Fluorescence spectra; DFT
资金
- Ministry of Education, Youth and Sports of the Czech Republic [CZ.1.07/2.3.00/30.0021]
A series of six keto-hydrazone dyes was prepared by azo coupling of diazotised substituted 2-aminophenols with pyrrolinone esters. All keto-hydrazone compounds were found as a mixtures of E and Z isomers by H-1 NMR. Irrespective to the position of nitro substituent on the phenol ring, all compounds fluoresce strongly only in solvent glass at 77 K except 4-nitro derivatives which also weakly fluoresce in solution and in solid-state at room temperature. Using these hydrazones as tridentate O-N-O' ligands, six symmetrical 2:1 octahedral Co(III) complexes were prepared. Multinuclear NMR combined with N-15 labelled hydrazone derivative proved that the starting mixture of hydrazone isomers was converted exclusively to E-azo configuration in complexes with coordinated nitrogen atoms coming solely from phenolic residues. The considerably different effect of 4- and 5-nitrophenol substituents on absorption spectra of the ligands and complexes was ascribed to prevailing azo character of an electronic structure of a ligand in the complex, based on TD DFT calculations. (C) 2013 Elsevier Ltd. All rights reserved.
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