Liquid-Crystalline and Electron-Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels-Alder Reactions on Perylenes

Alkyl esters, imides and imido‐esters of coronene‐tri‐, ‐tetra‐ and ‐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‐tetracarboxylic tetraesters. Coronenes substituted with a greatly variable number of electron‐withdrawing substituents are thus accessible, and di‐ and tetraimide derivatives are shown to be very pronounced electron‐acceptor materials. The tri‐ and tetraalkyl esters and imidoesters self‐assemble into columnar liquid‐crystalline phases. A multitude of coronene tri‐ to octacarboxylic derivatives (see figure) with variable self‐assembling and electronic properties have been obtained by the twofold sequential or simultaneous Diels–Alder reaction of alkyl acrylates and maleimides on perylenes.