新型咔唑类卟啉的合成与性能

Synthesis and Properties of Novel Carbazole Porphyrins

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 e V,-5.17 e V和-3.49 e V,-5.08 e V,两者的能级结构与纳米Ti O2的导带能级相匹配。

5,10,15,20-Tetrakis（ 4-carbazolephenyl） porphyrin（ TCPP） was prepared by using carbazole,p-fluorobenzaldehyde and pyrrole as the materials. 5,10,15,20-Tetrakis（ 4-nitrophenyl） porphyrin（ 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-Ncarbazolylbenzylideneiminophenyl） ] porphyrin（ TCIPP） was synthesized by the reaction of condensation of TNPP with carbazole benzaldehyde. The structures and properties were characterized by UVVis,1 H NMR,13 C 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 redshifted compared to TCPP. The LUMO and HOMO energy level of TCPP and TCIPP matched with energy level of nano-TiO2,with value of-3. 18 e V,-5. 17 e V and-3. 49 e V,-5. 08 e V,respectively.