Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 13, Issue 6, Pages 1746-1753Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200601416
Keywords
coronene; Diels-Alder reactions; liquid crystals; organic electronics; self-assembly
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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.
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