Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method

›› 2008, Vol. 16 ›› Issue (3): 369-372.

• SPECIAL ISSUE OF THE FIRST INTERNATIONAL SYMPOSIUM ON SUSTAINABLE CHEMICAL PRODUCT AND PROCESS ENGINEERING • Previous Articles Next Articles

Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method

SHE Yuanbin, FENG Lianshun, WANG Aixin, LI Xiuyan

Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100022, China

Received:2007-09-20 Revised:2008-02-17 Online:2008-06-28 Published:2008-06-28
Supported by:
Supported the National Natural Science Foundation of China (20776003,20576005);the Key Project of Natural Science Foundation of Beijing (2061001)

Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method

佘远斌, 冯连顺, 王爱欣, 李修艳

Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100022, China

通讯作者: SHE Yuanbin,E-mail:sheyb@bjut.edu.cn
基金资助:
Supported the National Natural Science Foundation of China (20776003,20576005);the Key Project of Natural Science Foundation of Beijing (2061001)

Abstract

Abstract: A novel method for synthesis of substitutedμ-oxo-bis[tetraphenyl porphyrinatoiron]compounds([TRPPFe]₂O) based on the reaction among free base porphyrins(TRPPH₂),FeSO₄·7H₂O and H₂O in one pot was proposed and investigated.Four kinds of[TRPPFe]₂O were synthesized by this novel synthetic method,and their structures were characterized by elemental analysis,infrared spectra and UV-vis spectroscopy.The reaction conditions,including the effect of different iron salts on the formation of[TRPPFe]₂O,the reaction time between FeSO₄·7H₂O and TRPPH₂,the molar ratio of FeSO₄·7H₂O/TRPPH₂ as well as the volume ratio of H₂O/DMF,were investigated.The [TRPPFe]₂O yield of 93%-98%could be obtained under the following optimal conditions:the reaction time of FeSO₄·7H₂O with TRPPH₂ was about 10 h,the molar ratio of FeSO₄·7H₂O/TRPPH₂ about 5:1,and the volume ratio of H₂O/DMF exceeded 2:1.Further research indicated that only TRPPFeCl were formed once FeSO₄·7H₂O was replaced by FeCl₂·4H₂O,the reason of which might be that halogen ions in iron salts interfered the formation of [TRPPFe]₂O,suggesting that halogen ions should be avoided in this novel synthetic method.

Key words: substituted μ-oxo-bis[tetraphenylporphyrinatoiron]compounds, one-pot method, free base porphyrins

摘要： A novel method for synthesis of substitutedμ-oxo-bis[tetraphenyl porphyrinatoiron]compounds([TRPPFe]₂O) based on the reaction among free base porphyrins(TRPPH₂),FeSO₄·7H₂O and H₂O in one pot was proposed and investigated.Four kinds of[TRPPFe]₂O were synthesized by this novel synthetic method,and their structures were characterized by elemental analysis,infrared spectra and UV-vis spectroscopy.The reaction conditions,including the effect of different iron salts on the formation of[TRPPFe]₂O,the reaction time between FeSO₄·7H₂O and TRPPH₂,the molar ratio of FeSO₄·7H₂O/TRPPH₂ as well as the volume ratio of H₂O/DMF,were investigated.The [TRPPFe]₂O yield of 93%-98%could be obtained under the following optimal conditions:the reaction time of FeSO₄·7H₂O with TRPPH₂ was about 10 h,the molar ratio of FeSO₄·7H₂O/TRPPH₂ about 5:1,and the volume ratio of H₂O/DMF exceeded 2:1.Further research indicated that only TRPPFeCl were formed once FeSO₄·7H₂O was replaced by FeCl₂·4H₂O,the reason of which might be that halogen ions in iron salts interfered the formation of [TRPPFe]₂O,suggesting that halogen ions should be avoided in this novel synthetic method.

关键词: substituted μ-oxo-bis[tetraphenylporphyrinatoiron]compounds, one-pot method, free base porphyrins

SHE Yuanbin, FENG Lianshun, WANG Aixin, LI Xiuyan. Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method[J]. , 2008, 16(3): 369-372.

佘远斌, 冯连顺, 王爱欣, 李修艳. Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method[J]. , 2008, 16(3): 369-372.

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Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method

Synthesis of Substituted μ-Oxo-bis[tetra-phenyl porphyrinatoiron] Compounds from Free Base Porphyrins by a One-pot Method

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