Room-Temperature Columnar Liquid-Crystalline Perylene Imido-Diesters by a Homogeneous One-Pot Imidification-Esterification of Perylene-3,4,9,10- tetracarboxylic Dianhydride - Centre de recherches Paul Pascal Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2011

Room-Temperature Columnar Liquid-Crystalline Perylene Imido-Diesters by a Homogeneous One-Pot Imidification-Esterification of Perylene-3,4,9,10- tetracarboxylic Dianhydride

Olivier Thiebaut
  • Fonction : Auteur
  • PersonId : 871543
Eric Grelet

Résumé

The reaction of PTCDA (perylene-3,4,9,10-tetracarboxylic dianhydride) with an alcohol, a bromoalkane, and an alkylamine in the presence of DBU in DMF yields imido-diestersubstituted perylenes. The reaction is limited to polar alcohols such as propanol, but longer alkyl chains are efficiently introduced in a second step by alkyl group exchange by using selective acidic ester hydrolysis that leaves the imide group intact. This amine-efficient approach to imidodiesters is used to obtain acceptor-type self-assembling dyes that form a hexagonal columnar liquid crystalline phase at room temperature.

Dates et versions

hal-00596781 , version 1 (30-05-2011)

Identifiants

Citer

Julien Kelber, Harald Bock, Olivier Thiebaut, Eric Grelet, Heinz Langhals. Room-Temperature Columnar Liquid-Crystalline Perylene Imido-Diesters by a Homogeneous One-Pot Imidification-Esterification of Perylene-3,4,9,10- tetracarboxylic Dianhydride. European Journal of Organic Chemistry, 2011, pp. 707-712. ⟨10.1002/ejoc.201001346⟩. ⟨hal-00596781⟩

Collections

CNRS CRPP INC-CNRS
129 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Facebook X LinkedIn More