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Nonsymmetrical 3,4-Dithienylmaleimides by Cross-Coupling Reactions with Indium Organometallics: Synthesis and Photochemical Studies.

Authors :
Mosquera, Ángeles
Férnandez, M. Isabel
Canle Lopez, Moisés
Pérez Sestelo, José
Sarandeses, Luis A.
Source :
Chemistry - A European Journal; Oct2014, Vol. 20 Issue 44, p14524-14530, 7p
Publication Year :
2014

Abstract

The synthesis and photochemical study of novel nonsymmetrical 1,2-dithienylethenes (DTEs) with a maleimide bridge have been carried out. The synthetic approach to the DTEs was based on successive selective palladium-catalyzed cross-coupling reactions of 5-susbtituted-2-methyl-3-thiophenyl indium reagents with 3,4-dichloromaleimides. The required organoindium reagents were prepared from 2-methyl-3,5-dibromothiophene by a selective (C-5) coupling reaction with triorganoindium compounds (R<subscript>3</subscript>In) and subsequent metal-halogen exchange. The coupling reactions usually gave good yields and have a high atom economy with substoichiometric amounts of R<subscript>3</subscript>In. The results of photochemical studies show that these novel dithienylmaleimides undergo a photocyclization reaction upon irradiation in the UV region and a photocycloreversion after excitation in the visible region, thus they can be used as photochemical switches. ON-OFF operations can be repeated in successive cycles without appreciable loss of effectiveness in the process. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09476539
Volume :
20
Issue :
44
Database :
Complementary Index
Journal :
Chemistry - A European Journal
Publication Type :
Academic Journal
Accession number :
98982172
Full Text :
https://doi.org/10.1002/chem.201403736