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- Title
Stable Diindeno‐Fused Corannulene Regioisomers with Open‐Shell Singlet Ground States and Large Diradical Characters.
- Authors
Lu, Ru‐Qiang; Wu, Shuang; Yang, Lin‐Lin; Gao, Wen‐Bin; Qu, Hang; Wang, Xiao‐Ye; Chen, Jun‐Bo; Tang, Chun; Shi, Hai‐Yan; Cao, Xiao‐Yu
- Abstract
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 C104, 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 π system. Although the DIC compounds have large diradical characters, they display excellent stability under ambient conditions. The half‐lives are 37 days for DIC‐1 and 6.6 days for DIC‐2 in solution. This work offers a new design strategy towards diradicaloids with large diradical characters yet maintain high stability.
- Subjects
CORANNULENE; ISOMERS; FULLERENES; BIRADICALS; AROMATIZATION
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 23, p7682
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201902028