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Published on: May 21, 2019
Oxidations of (2,2'-Diphenyl)ethylidene-Bridged Porphyrin Dimers
Ye Xiao1, Jiale Tang1, Ling Xu1
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research, Ministry of Education, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China.
Abstract:
Oxidation reactions of (2,2'-diphenyl)ethylidene-bridged porphyrin dimers were examined for the synthesis of (2,2'-diphenyl)ethylidene-inserted porphyrin arch tape dimers. These reactions provided, in addition to the target arch tape dimers, unexpected products such as a bicyclo[3.3.0]octane-fused porphyrin dimer, a (2,2'-fluorenyl)ethylidene-inserted porphyrin arch tape dimer, and a meso- and ortho-phenyl-linked free base dimer, depending upon the substrate and reaction conditions, demonstrating the high promise of these porphyrin substrates. The target arch tape dimers, which were synthesized by the oxidation with DDQ and CF3SO3H, exhibit red-shifted and enhanced Q-bands and small electrochemical HOMO-LUMO gaps, indicating effective conjugation.
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