Columnar Liquid‐Crystalline Dibenzopentacenodithiophenes by Photocyclization

Research paper by Marilia G. Belarmino Cabral, Dr. Deise M. Pereira de Oliveira Santos, Ahmed Bentaleb, Dr. Elizabeth A. Hillard, Prof. Dr. Rodrigo Cristiano, Prof. Dr. Hugo Gallardo, Dr. Fabien Durola, Dr. Harald Bock

Indexed on: 04 May '16Published on: 03 May '16Published in: Chemistry - A European Journal


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.