Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 8, Pages 2209-2213Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712961
Keywords
antiaromaticity; diradicals; porphyrinoid; ring current
Categories
Funding
- JSPS KAKENHI [JP26102003, JP15K21721, JP17H05157]
- Program for Leading Graduate Schools Integrative Graduate Education and Research in Green Natural Sciences from MEXT
- JSPS Research Fellowship [JP16J10315]
- Murata Science Foundation
- Global Research Laboratory - Ministry of Science, ICT and Future Planning [2013K1A1A2A02050183]
- Grants-in-Aid for Scientific Research [17H05157, 16J10315, 25248007] Funding Source: KAKEN
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Fused benzene rings to antiaromatic compounds generally improve their stability but attenuate their antiaromaticity. The opposite case is now reported. Ni-II benzonorcorroles were synthesized and the effect of benzo-fusion on the antiaromaticity was elucidated. The benzo-fusion resulted in significant decrease of the HOMO-LUMO gaps and enhancement of the paratropic ring current effect. Furthermore, the introduction of the benzo groups induced singlet diradical character in the antiaromatic porphyrinoid.
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