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Reaction of meso-aryl-substituted dipyrromethanes with tetracyanoethylene led to generation of a mono-tricyanovinyl-substituted species as well as an expanded dipyrrin analogue bearing both a dicyanomethylene and a tricyanovinyl substituent at the α-positions. These novel compounds exhibit absorption spectral features perturbed by the electron-withdrawing substituents. Unique protonation-induced spectral changes were also disclosed. 相似文献
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Jiping Hao Akihide Nishiyama Dr. Shigeki Mori Prof. Dr. Ko Furukawa Prof. Dr. Soji Shimizu 《Angewandte Chemie (International ed. in English)》2023,62(34):e202307862
5,15-Dioxaporphyrin ( DOP ) is a novel meso-oxaporphyrin analogue and exhibits unique 20π-antiaromaticity, unlike its mother congener of 18π-aromatic 5-oxaporphyrin, commonly known as its cationic iron complex called verdohem, which is a key intermediate of heme catabolism. To reveal its reactivities and properties as an oxaporphyrin analogue, the oxidation of tetra-β-arylated DOP ( DOP-Ar4 ) was explored in this study. Stepwise oxidation from the 20π-electron neutral state was achieved, and the corresponding 19π-electron radical cation and 18π-electron dication were characterized. Further oxidation of the 18π-aromatic dication resulted in the formation of a ring-opened dipyrrindione product by hydrolysis. Considering a similar reaction of verdoheme to ring-opened biliverdin in the heme degradation in nature, the current result consolidates the ring-opening reactivity of oxaporphyrinium cation species. 相似文献