Acetic Acid/Oxygen Route for Efficient Synthesis of Substituted Porphyrin

doi:10.11944/j.issn.1000-0518.2020.03.190271

Chinese Journal of Applied Chemistry ›› 2020, Vol. 37 ›› Issue (3): 264-270.DOI: 10.11944/j.issn.1000-0518.2020.03.190271

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Acetic Acid/Oxygen Route for Efficient Synthesis of Substituted Porphyrin

GUO Hongchen^a^b,QIN Yusheng^a,WANG Xianhong^a^b^*()

^a Key Laboratory of Polymer Ecomaterials,Changchun Institute of Applied Chemistry, Chinese Academy of Sciences,Changchun 130022,China
^b University of Chinese Academy of Sciences,Beijing 100049,China

Received:2019-10-14 Accepted:2019-12-18 Published:2020-03-01 Online:2020-03-10
Contact: WANG Xianhong
Supported by:
Supported by the Key Research Program of the Chinese Academy of Sciences(ZDRW-CN-2018-2)

Abstract

Abstract:

Recently, efficient synthesis of porphyrin has become increasingly interesting in demand of many discoveries in metalloporphyrin complexes, especially for their excellent catalytic performances. Porphyrin is a conjugated macrocyclic compound composed of four pyrrole rings connected by methenylene. The state-of-the-art porphyrin synthesis includes propionic acid method and acetic acid/nitrobenzene method, but both suffer from low yield, high cost and heavy environmental pollution. In this work, an acetic acid/oxygen route for substituted porphyrin synthesis was developed, where the reaction temperature was kept at 120 ℃, while O₂ was fed only in the first 30 min under reactant concentration of 0.24 mol/L, leading to tetra(4-bromophenyl)porphyrin in the yield of 53.8%. It should be noted that the acetic acid/oxygen route allows the concurrence of macrocyclic framework formation and oxidation, which provides a viable strategy for efficient porphyrin synthesis in convenient and less environment loading way.

Key words: porphyrin, substituted porphyrin, acetic acid, oxygen

GUO Hongchen, QIN Yusheng, WANG Xianhong. Acetic Acid/Oxygen Route for Efficient Synthesis of Substituted Porphyrin[J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 264-270.

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Acetic Acid/Oxygen Route for Efficient Synthesis of Substituted Porphyrin

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