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Heptatriene-Fused BIII Subporphyrins
Xiaorong Jin1, Min Wang1, Yutao Rao1
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:
Singly and doubly cycloheptatriene-fused BIII subporphyrins 3 and 6 were synthesized from BIII meso-(2-formylphenyl)-subporphyrin and BIII meso-(2,6-diformylphenyl) subporphyrin, respectively, via a sequence of Wittig methoxymethylenation and acid-catalyzed cyclization. Naphthalene- and benzocycloheptatriene-fused BIII subporphyrin 9 was obtained along with side products 10 and 11 by intramolecular McMurry coupling of BIII 3,7-di(2-formylphenyl)-subporphyrin and subsequent intramolecular oxidative annulation. BIII subporphyrin 9 displays altered optical and electrochemical properties.
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