open access

https://hdl.handle.net/2115/14770

Tetraaryl-o-quinodimethanes: Reductive Generation and Severely Distorted Geometry

日本語

dye

2006-09

有機合成化学協会

64(9)

958-968

Introduction of four aryl groups on the highly reactive o-quinodimethane (o-QDM) skeleton suppresses the intermolecular reactivities. Thus, the unimolecular isomerization through electrocyclization is the major decomposition path for title molecules. Rational design can prevent thermal isomerization of Ar4-o-QDMs. A new general procedure to generate Ar4-o-QDM has been established here that includes two-electron reduction of the corresponding dications, whose reaction conditions no longer promote electrocyclization of Ar4-o-QDM. Several derivatives of Ar4-o-QDM with the dihydrophenanthrene, dibenzoperylene, or acenaphthene skeleton were isolated for the first time, and the details on their highly strained molecular structures were investigated by low-temperature X-ray analyses. Based on the reversible interconversion between Ar4-o-QDMs and the precursor dications, they represent a new class of electrochromic redox pairs.

学術雑誌論文

Accepted Manuscript

©有機合成化学協会

0037-9980