Liquid-crystalline and electron-deficient coronene oligocarboxylic esters and imides by twofold benzogenic Diels-Alder reactions on perylenes |
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Authors: | Alibert-Fouet Sonia Seguy Isabelle Bobo Jean-François Destruel Pierre Bock Harald |
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Institution: | Centre de Recherche Paul Pascal, CNRS, 115, av. Schweitzer, 33600 Pessac, France. |
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Abstract: | 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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Keywords: | coronene Diels–Alder reactions liquid crystals organic electronics self‐assembly |
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