可溶性的含羧基苝酰亚胺类化合物的合成及其光谱性质研究  

Synthesis and Spectra Properties of Soluble Perylene Bisimides with Carboxylic Groups

作　　者：洪心进[1] 罗倩[1] 王春祥[1] 薛敏钊[1] 张青[1] 盛巧蓉[1] 刘燕刚[1] 

机构地区：[1]上海交通大学化学化工学院精细化工研究所,上海200240

出　　处：《感光科学与光化学》2006年第3期167-172,共6页Photographic Science and Photochemistry

摘　　要：本文主要以酐(1)为起始物,通过在环母体结构的1、6、7、12位上引入苯氧基和对甲基苯氧基合成了另外两种酐化合物(2a和2b);所得到的酐化合物与6-氨基已酸进行反应,合成了3种可溶性的含有羧基的酰亚胺化合物(3a、3b和3c),使用红外、紫外、荧光1、H-NMR,元素分析对所合成的化合物进行了表征.经研究发现,环母体结构的1、6、7、12位上苯氧基和对甲基苯氧基的引入,能使得所合成的含羧基酰亚胺类化合物的最大吸收波长分别红移了44.1 nm和50.1 nm;Stokes位移变大,分别为34.1 nm和30.0 nm;而荧光量子产率有所降低但下降趋势不明显.Three soluble perylene bisimides with carboxylic groups： N, N＇-bis（5-carboxy-pentyl）- 1, 6, 7, 12-tetraphenoxy-3, 4, 9, 10-perylene bisimide （3a）, N, N＇-bis（5-carboxy-pentyl）-l, 6, 7, 12-tetra（methyl-phenoxy）-3, 4, 9, 10-perylene bisimide （3b） and N, N＇-bis（5-carboxy- pentyl）-3, 4, 9, 10-perylene bisimide （3c） are synthesized by the reaction of 6-amino-caproic acid and 3, 4, 9, 10-perylene tetracarboxy anhydride （1） and its two derivatives （2a, 2b） which are synthesized through inducing four phenoxy groups and four methyl-phenoxy groups at the positions 1, 6, 7, and 12 of 3, 4, 9, 10-perylene tetracarboxy anhydride （1） respectively. Their structures are confirmed by IR, ^1H-NMR and dement analysis, Their photoscopic properties are characterized by UV-Vis absorption spectra and fluorescence spectra. The red shifts of 44 nm and 54 nm mad Stokes shifts of 34.1 nm and 30.0 nm of perylene bisimides are attributed to the introduction of four phenoxy groups and four methyl-phenoxy groups at the positions 1, 6, 7, and 12 of 3, 4, 9, 10- perylene tetracarboxy anhydride respectively, while decreases of their fluorescence quantum yields are not obvious.

关 键 词：苝酰亚胺 羧基 吸收光谱 荧光光谱 

分 类 号：O621.25[理学—有机化学]