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. 2017 Mar;82(3):342-346.
doi: 10.1002/cplu.201600566. Epub 2016 Dec 28.

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

Marília Gabriela Belarmino Cabral  1   2 , Deise Maria Pereira de Oliveira Santos  1 , Rodrigo Cristiano  2 , Hugo Gallardo  3 , Ahmed Bentaleb  1 , Elizabeth A Hillard  1 , Fabien Durola  1 , Harald Bock  1
Affiliations

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

Marília Gabriela Belarmino Cabral et al. Chempluschem. 2017 Mar.

Abstract

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.

Keywords: arenes; dehydrogenation; fused-ring systems; liquid crystals; stacking interactions.

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