AN IMPROVED SYNTHESIS OF DI-NITRO-FUNCTIONALIZED TRANS-A(2)B(2)-TETRAPHENYLPORPHYRINS

作者：Zhang, Zheng-Lin^*; She, Yuan-Bin; Fu, Hai-Yan; Song, Xu-Feng; Sun, Zhi-Cheng

来源：Heterocycles, 2014, 89(2): 503-514.

DOI：10.3987/COM-13-12903

• REGIOSPECIFIC ARYL NITRATION
• ASYMMETRIC CYCLOPROPANATION
• MESO-TETRAARYLPORPHYRINS
• SELECTIVE SYNTHESIS
• POTENTIAL USE
• SOLAR-CELLS
• PORPHYRINS
• COBALT
• TETRAPHENYLPORPHYRIN
• ROUTE

An improved MacDonald-type 2+2 condensation was used to synthesize a series of di-nitro-functionalized trans-A(2)B(2)-tetraphenylporphyrins, and all the structures were characterized by melting point analysis, electronic absorption spectroscopy, infrared spectroscopy, H-1 NMR spectroscopy, high-resolution mass spectroscopy, and elemental analysis. The synthesis process was systematically investigated, and several important factors were examined to increase the product yield. The optimum reaction conditions were then established, and the method was found to have the advantages of high reactant concentration, no quinone as oxidant, and good yields of 5,15-bis(p-nitrophenyl)-10,20-bis(p-R-phenyl)porphyrins (R = H, F, Cl, Br, Me, and MeO). Moreover, side reactions, such as scrambling, could be suppressed easily by regulating reaction condition.

• 出版日期2014-2-1
• 单位中南民族大学; 北京工业大学; 北京印刷学院