Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 23, Pages 7600-7605Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201902028
Keywords
corannulene; macrocycles; polycycles; radicals; structure elucidation
Categories
Funding
- 973 Program [2015CB856505]
- NSFC [21722304, 91427304, 21573181, 91227111]
- Top-Notch Young Talents Program of China
- Fundamental Research Funds for the Central Universities of China [20720160050]
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The synthesis of open-shell polycyclic hydrocarbons with large diradical characters is challenging because of their high reactivities. Herein, two diindeno-fused corannulene regioisomers DIC-1 and DIC-2, curved fragments of fullerene C-104, were synthesized that exhibit open-shell singlet ground states. The incorporation of the curved and non-alternant corannulene moiety within diradical systems leads to significant diradical characters as high as 0.98 for DIC-1 and 0.89 for DIC-2. Such high diradical characters can presumably be ascribed to the re-aromatization of the corannulene pi system. Although the DIC compounds have large diradical characters, they display excellent stability under ambient conditions. The half-lives are 37days for DIC-1 and 6.6days for DIC-2 in solution. This work offers a new design strategy towards diradicaloids with large diradical characters yet maintain high stability.
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