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Synthesis and Aromaticity of Benzene-Fused Doubly N-Confused Porphyrins |
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| Authors: | Prof Hidemitsu Uno Kota Muramatsu Shogo Hiraoka Hiroyuki Tahara Mako Hirose Eidai Tamura Tatsumi Shiraishi Dr John Mack Prof Nagao Kobayashi Dr Shigeki Mori Dr Tetsuo Okujima Dr Masayoshi Takase |
| Institution: | 1. Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577 Japan;2. Institute for Nanotechnology Innovation, Department of Chemistry, Rhodes University, Grahamstown, 6140 South Africa;3. Faculty of Textile Science and Technology, Shinshu University, Ueda, 386-8567 Japan;4. Advanced Research Support Center, Ehime University, Matsuyama, 790-8577 Japan |
| Abstract: | A bicyclo2.2.2]octadiene(BCOD)-fused bis(dipyrromethane) derivative was reacted with methylal in the presence of trifluoroacetic acid followed by oxidation with chloranil to give a doubly N-confused phlorin derivative, which did not undergo the retro-Diels–Alder reaction extruding an ethylene molecule on heating. In contrast, a 7-tert-butoxybicyclo2.2.1]heptadiene(7-BuOBCHD)-fused bis(dipyrromethane) yielded benzene-ring-fused doubly N-confused porphyrins by following similar reaction sequences. |
| Keywords: | aromaticity macrocycles porphyrins proton–deuteron exchange |