Liquid-Crystalline and Electron-Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels–Alder Reactions on Perylenes
Résumé
Alkyl esters, imides and imido-esters of coronene-tri-, -tetraand-octacarboxylic acids are accessible by a twofold oxidative benzogenic Diels–Alder reaction. Alkyl acrylates add to perylene, and maleic alkyl imides react twice with perylene as well as with perylene-tetracarboxylictetraesters. Coronenes substituted with a greatly variable number of electron with drawing substituents are thus accessible, and di- and tetraimide derivatives are shown to be very pronounced electron-acceptor materials. The triand tetraalkyl esters and imidoesters self-assemble into columnar liquid-crystalline phases.