第 47 卷第 5 期 Vol. 47 No. 5 2017 年 10 月 Oct 2017

所属栏目：染料、颜料及涂料 偶氮卟啉染料的制备及性能研究

王振兴，刘思雨，张 晓，张学俊* （中北大学 理学院，山西 太原 030051）

摘　要：以meso-四（4-硝基苯基）卟啉为原料经硝基还原后制得meso-四（4-氨基苯基）卟啉，meso-四（4-氨基苯基）卟啉再经重氮化后分别与2-萘酚和8-羟基喹啉发生偶合反应得到meso-四［4-（2-羟基偶氮萘基）苯基］卟啉（卟啉1）和meso-四［4-（8-羟基偶氮喹啉）苯基］卟啉（卟啉2）。利用核磁共振氢谱、IR、UV-Vis、循环伏安法等确定了目标化合物的结构、光谱特征和电化学性能。紫外-可见光光谱测试结果表明，卟啉1和卟啉2的Q带与meso-四（4-氨基苯基）卟啉相比，吸收强度明显增强，并且卟啉2与卟啉1相比，在可见光区有明显的红移现象。用循环伏安法研究了两种偶氮卟啉染料的氧化还原性质，通过计算ELUMO和EHOMO值，得出其能级结构与纳米TiO2的导带能级相匹配。

关键词：卟啉；偶氮；染料；吸收光谱

中图分类号：O634　　文献标识码：A　　文章编号：1009-9212（2017）05-0038-05

Preparation and Properties of Azo-bridged Porphyrin Dyes

WANG Zhen-xing, LIU Si-yu, ZHANG Xiao, ZHANG Xue-jun* (College of Science, North University of China,Taiyuan 030051, China)

Abstract：Meso-tetra (4-aminophenyl) porphyrin was prepared by reduction of meso-tetra (4-nitrophenyl) porphyrin. Meso-tetra(4-aminophenyl) porphyrin was respectively reacted with 2-naphthol and 8-hydroxyquinoline by diazotization-coupling to give meso-tetra[4-(2-hydroxy-naphthylazo) phenyl] porphyrin (porphyrin 1) and meso-tetra [4-(8-hydroxy-quinolinylazo) phenyl] porphyrin (porphyrin 2). Molecular structures of target compounds were elucidated by NMR. The spectral characteristics and electrochemical properties of target compounds were characterized by UV-vis, IR, cyclic voltammograms.The results of UV-Vis spectroscopy showed that the Q-bands of porphyrin 1 and porphyrin 2 were significantly enhanced compared with that of meso-tetra (4-aminophenyl) porphyrin.Porphyrin 2 had obvious redshift phenomenon in visible region compared with porphyrin 1. The cyclic voltammetry studies indicated that the LUMO and HOMO energy level of target compounds matched with energy level of nano-TiO2.

Key words：porphyrin; azo; dye; absorption spectrum

基金项目：山西省回国留学人员科研资助项目（2015-078），山西省自然科学基金资助项目（2015011011）。

作者简介：王振兴（1989-），男，河北张家口人，硕士研究生，主要从事功能有机分子的合成及性能研究（E-mail：410963542@qq.com）。

联 系 人：张学俊，教授，博士，主要从事功能有机分子的合成及性能研究（E-mail：zhangxuejun@nuc.edu.cn）。

收稿日期：2017-09-20