In:
Angewandte Chemie, Wiley, Vol. 134, No. 23 ( 2022-06-07)
Abstract:
Open‐shell non‐alternant polycyclic hydrocarbons (PHs) are attracting increasing attention due to their promising applications in organic spintronics and quantum computing. Herein we report the synthesis of three cyclohepta[ def ]fluorene‐based diradicaloids ( 1 – 3 ), by fusion of benzo rings on its periphery for the thermodynamic stabilization, as evidenced by multiple characterization techniques. Remarkably, all of them display a very narrow optical energy gap ( E g opt =0.52–0.69 eV) and persistent stability under ambient conditions ( t 1/2 =11.7–33.3 h). More importantly, this new type of diradicaloids possess a low‐lying triplet state with an extremely small singlet–triplet energy gap, as low as 0.002 kcal mol −1 , with a clear dependence on the molecular size. This family of compounds thus offers a new route to create non‐alternant open‐shell PHs with high‐spin ground states, and opens up novel possibilities and insights into understanding the structure–property relationships.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v134.23
DOI:
10.1002/ange.202202170
Language:
English
Publisher:
Wiley
Publication Date:
2022
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