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■ An Improved Synthesis of Di-Nitro-Functionalized trans-A2B2-Tetraphenylporphyrins

Zheng-Lin Zhang, Yuan-Bin She,* Hai-Yan Fu,* Xu-Feng Song, and Zhi-Cheng Sun

*Department of Chemistry & Chemical Engineering, Institute of Green Chemistry & Fine Chemicals, Beijing University of Technology, 100 Ping Le Yuan, Chaoyang District, Beijing 100124, China

Abstract

An improved Macdonald-type 2+2 condensation was used to synthesize a series of di-nitro-functionalized trans-A2B2-tetraphenylporphyrins, and all the structures were characterized by melting point analysis, electronic absorption spectroscopy, infrared spectroscopy, 1H 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, CH3, and CH3O). Moreover, side reactions, such as scrambling, could be suppressed easily by regulating reaction condition.