meso-Diazacorrphycenes: Neighboring Effect of Two Nitrogen Atoms |
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Authors: | Atsumi Yagi Prof Dr Hiroshi Shinokubo |
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Institution: | Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, 464-8603 Japan |
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Abstract: | The neighboring effect of two adjacent heteroatoms influences the structures and properties of heterocyclic compounds. Herein, we demonstrated that the introduction of two adjacent sp2 nitrogen atoms into a porphyrinic skeleton significantly enhanced its Brønsted basicity due to the repulsive interaction between two lone pairs on the nitrogen atoms. Palladium- and copper-templated ring closure of dichlorobis(dipyrrin) with hydrazine hydrate provided meso-diazacorrphycene palladium and copper complexes in good yields. The structural, magnetic, and electrochemical properties of the diazacorrphycene complexes were investigated experimentally and theoretically to elucidate the effect of the meso-nitrogen atoms. |
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Keywords: | aromaticity basicity neighboring effect nitrogen porphyrinoid |
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