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Article Dans Une Revue ChemPlusChem Année : 2017

From 1,4-Phenylenebis(phenylmaleate) to a Room-Temperature Liquid-Crystalline Benzo[ghi]perylene Diimide

Résumé

The photocyclization of tetraethyl 1,4‐phenylenebis(phenylmaleate) in the presence of iodine and oxygen predominantly yields tetraethyl [5]helicene‐5,6,9,10‐tetracarboxylate, together with small amounts of tetraethyl dibenz[a,h]anthracene‐5,6,12,13‐tetracarboxylate and tetraethyl benzo[ghi]perylene‐3,4,11,12‐tetracarboxylate. The helicene tetraester is planarized to the benzoperylene tetraester by Scholl reaction with AlCl3 followed by reesterification of the partially hydrolyzed crude product. Subsequent treatment with a branched alkylamine yields a columnar liquid‐crystalline benzoperylene diimide whose mesophase is stable at room temperature despite its limited and non‐centrosymmetric alkyl periphery. Its absorption spectrum is markedly red‐shifted compared to that of a similar benzoperylene triimide.

Domaines

Chimie organique
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Dates et versions

hal-01543615 , version 1 (02-02-2021)

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Marilia Gabriela Belarmino Cabral, Deise Maria Pereira de Oliveira Santos, Rodrigo Cristiano, Hugo Gallardo, Ahmed Bentaleb, et al.. From 1,4-Phenylenebis(phenylmaleate) to a Room-Temperature Liquid-Crystalline Benzo[ghi]perylene Diimide. ChemPlusChem, 2017, 82 (3), pp.342-346. ⟨10.1002/cplu.201600566⟩. ⟨hal-01543615⟩

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