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新型咔唑类卟啉的合成与性能

             

摘要

以咔唑、对氟苯甲醛和吡咯为原料制得meso-四(4-咔唑)苯基卟啉(TCPP).以对硝基苯甲醛与吡咯为原料制得meso-四(4-硝基)苯基卟啉(TNPP); TNPP经还原反应制得meso-四(4-氨基苯基)卟啉(TAPP); TAPP与咔唑苯甲醛经缩合反应制得新型meso-四[对-(P-N-咔唑基亚苄基亚氨基)]苯基卟啉(TCIPP),其结构和性能经UV-Vis, 1H NMR, 13C NMR, IR,元素分析和循环伏安法(CV)表征.结果表明:TCPP在270~300 nm处有新吸收峰;TCIPP的Q 带和 B 带相比于 TCPP 有明显红移. TCPP 和 TCIPP 的 ELUMO和 EHOMO分别为 -3.18 eV,-5.17 eV和-3.49 eV,-5.08 eV,两者的能级结构与纳米TiO2的导带能级相匹配.%5,10,15,20-Tetrakis(4-carbazolephenyl) porphyrin(TCPP) was prepared by using carbaz-ole, p-fluorobenzaldehyde and pyrrole as the materials.5,10,15,20-Tetrakis(4-nitrophenyl) porphy-rin(TNPP) was obtained by the reaction of p-nitrobenzaldehyde and pyrrole.5,10,15,20-Tetrakis(4-aminophenyl) porphyrin(TAPP) was prepared by reduction of TNPP.5,10,15,20-Tetrakis[P-(P-N-carbazolylbenzylideneiminophenyl)] porphyrin(TCIPP) was synthesized by the reaction of condensa-tion of TNPP with carbazole benzaldehyde.The structures and properties were characterized by UV-Vis, 1H NMR, 13C NMR, IR, elemental analysis and cyclic voltammograms( CV).The results showed that TCPP has a new absorption at 270~300 nm.The Q band and B band of TCIPP has obvious red-shifted compared to TCPP.The LUMO and HOMO energy level of TCPP and TCIPP matched with ener-gy level of nano-TiO2, with value of -3.18 eV,-5.17 eV and -3.49 eV,-5.08 eV, respectively.

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