Affiliation:
1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic Solids CAS Center of Excellence in Molecular Science Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China
2. School of Chemical Sciences University of Chinese Academy of Sciences Beijing 100049 China
3. College of Chemistry and Molecular Engineering Peking University Beijing 100871 China
Abstract
AbstractNon‐benzenoid acenes containing heptagons have received increasing attention. We herein report a heptacene analogue containing a quinoidal benzodi[7]annulene core. Derivatives of this new non‐benzenoid acene were obtained through an efficient synthetic strategy involving an Aldol condensation and a Diels–Alder reaction as key steps. The configuration of this heptacene analogue can be modulated from a wavy to a curved one by just varying the substituents from a (triisopropylsilyl)ethynyl group to a 2,4,6‐triisopropylphenyl (Trip) group. When mesityl (Mes) groups are linked to the heptagons, the resulting non‐benzenoid acene displays polymorphism with a tunable configuration from a curved to a wavy one upon varying the crystallization conditions. In addition, this new non‐benzenoid acene can be oxidized or reduced by NOSbF6or KC8to the respective radical cation or radical anion. Compared with the neutral acene, the radical anion shows a wavy configuration and the central hexagon becomes aromatic.
Funder
National Natural Science Foundation of China
Youth Innovation Promotion Association of the Chinese Academy of Sciences
CAS-Croucher Funding Scheme for Joint Laboratories