光谱学与光谱分析 |
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Synthesis and Spectral Characteristics of Novel Di-Schiff Base Derivatives Incorporting Oxadiazole Ring |
CHEN Tong-bin1,2, ZHANG Xiong-lu1*, FAN Xiao-lin1,LI Xun1 |
1. Key Laboratory of Organo-Pharmaceutic Chemistry of Jiangxi Province, Gannan Normal College, Ganzhou 341000, China 2. Department of Chemistry, Hanshan Normal College, Chaozhou 521041,China |
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Abstract 4-nitrobenzoic acid and hydraxine sulfate were cyclized with H3PO4/P2O5 to afford 2,5-bis(4-nitrophenyl)-1,3,4-oxadiazole(1), then(1)was reduced to 2,5-bis(4-aminophenyl)-1,3,4-oxadiazole using Zn/CaCl2 as reduction reagent, and at last, a series of novel di-schiff base derivatives containing oxadiazole ring were obtained by the reaction of 2,5-bis(4-aminophenyl)-1,3,4-oxadiazole with aromatic aldehydes (yield:65%-81%). The structures of these compounds were confirmed by 1H NMR, FTIR and MS. Their UV-Vis spectra as well as fluorescence spectra were studied and the electrochemical properties were tested with cyclic voltammetry. The UV-Vis spectroscopy results show that the characteristic absorption peaks of 1,3, 4-oxadiazole unit and di-schiff base unit disappeared. The maximum absorption wavelength was detected at 345-357 nm because conjugation effect made the two energy bands partially hybrid and form a new energy band structure. Fluorescence spectroscopy results show that they emit strong blue and purple fluorescence, and the emission maximum wavelengths of di-schiff base are from 390 to 407 nm. Electrochemical properties results show that they have higher affinity energy (2.36-3.04 eV) and ionic potential (5.35-6.06 eV), which indicated that they have better electron-transporting properties than PBD except 3 a and 3 h. The results give a reference to further application to organic electroluminescent devices of the target compound.
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Received: 2007-05-16
Accepted: 2007-08-26
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Corresponding Authors:
ZHANG Xiong-lu
E-mail: zhangxionglu@sina.com
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