title: Columnar Liquid-Crystalline Dibenzopentacenodithiophenes by Photocyclization.
abstract: The twofold glyoxylic Perkin reaction of perylene-3,9-diglyoxylic acid with thiophene-diacetic acid followed by oxidative photocylization and reaction with α-branched primary alkylamines yields columnar liquid-crystalline diimides with two sulfur atoms in the condensed arene system. A broad temperature range of the hexagonal columnar mesophase is induced by racemic doubly branched alkyl chains. The HOMO and LUMO energy levels of these thiophene-derived diimides qualify them as electron donors with respect to perylene diimides.
authors.affiliation: Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600, Pessac, France.|Departamento de Química, Universidade Federal da Paraíba, CEP, 58051-900, João Pessoa, Paraíba, Brazil.
authors.forename: Marilia G Belarmino
authors.initials: MG
authors.lastname: Cabral
authors.affiliation: Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600, Pessac, France.
authors.forename: Deise M
authors.initials: DM
authors.lastname: Pereira de Oliveira Santos
authors.affiliation: Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600, Pessac, France.
authors.forename: Ahmed
authors.initials: A
authors.lastname: Bentaleb
authors.affiliation: Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600, Pessac, France.
authors.forename: Elizabeth A
authors.identifier: 0000-0002-5149-0324
authors.initials: EA
authors.lastname: Hillard
authors.affiliation: Departamento de Química, Universidade Federal da Paraíba, CEP, 58051-900, João Pessoa, Paraíba, Brazil.
authors.forename: Rodrigo
authors.initials: R
authors.lastname: Cristiano
authors.affiliation: Departamento de Química, Universidade Federal de Santa Catarina, CEP, 88040-900, Florianópolis,Santa Catarina, Brazil.
authors.forename: Hugo
authors.initials: H
authors.lastname: Gallardo
authors.affiliation: Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600, Pessac, France.
authors.forename: Fabien
authors.initials: F
authors.lastname: Durola
authors.affiliation: Centre de Recherche Paul Pascal, CNRS & Université de Bordeaux, 115, av. Schweitzer, 33600, Pessac, France. bock@crpp-bordeaux.cnrs.fr.
authors.forename: Harald
authors.identifier: 0000-0002-0479-8203
authors.initials: H
authors.lastname: Bock
keywords: liquid crystals; photooxidation; stacking interactions; sulfur heterocycles; thiophene