Synthesis of π-Extended Thiele's and Chichibabin's Hydrocarbons and Effect of the π-Congestion on Conformations and Electronic States.

ABSTRACT: The biradicaloid of Chichibabin's hydrocarbon exits in a unique thermal equilibrium between closed-shell singlet and open-shell triplet forms. Conceptually, the incorporation of nonplanar aromatic groups, such as anthraquinodimethane (AQD), in these species could bring about stabilization of the individual singlet and triplet spin biradicaloids by creating a high energy barrier for conformational interconversion between folded (singlet) and twisted (triplet) forms. Moreover, this alteration could introduce the possibility of controlling spin states through conformational changes induced by chemical and physical processes. Herein, we report the preparation of AQD-containing, π-extended Thiele's (A-TH) and Chichibabin's (A-CH) hydrocarbons, which have highly π-congested structu

SUBMITTER: Nishiuchi T 

PROVIDER: S-EPMC9136924 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature