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Synthesis and Spectra Properties of Soluble Perylene Bisimides with Carboxylic Groups
- HONG Xin-jin, LUO Qian, WANG Chun-xiang, XUE Min-zhao, ZHANG Qing, SHENG Qiao-rong, LIU Yan-gang
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2006, 24(3):
167-172.
DOI: 10.7517/j.issn.1674-0475.2006.03.167
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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 (5carboxy-pentyl)-1,6,7,12-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 methylphenoxy 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 element analysis,Their photoscopic properties are characterized by UV-Vis absorption spectra and fluorescence spectra.The red shifts of 44 nm and 54 nm and 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.