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The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

The Optimization of Direct Heteroarylation and Sonogashira Cross-Coupling Reactions as Efficient and Sustainable Synthetic Methods To Access π-Conjugated Materials with Near-Infrared Absorption

Authors :
Gregory C. Welch
Pierre Josse
Seth M. McAfee
Jonathan Cann
P. Blanchard
Clément Cabanetos
Department of Chemistry, University of Calgary
University of Calgary
MOLTECH-Anjou
Université d'Angers (UA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Source :
ACS Sustainable Chemistry & Engineering, ACS Sustainable Chemistry & Engineering, American Chemical Society, 2016, 4 (6), pp.3504-3517. ⟨10.1021/acssuschemeng.6b00554⟩
Publication Year :
2016
Publisher :
HAL CCSD, 2016.

Abstract

International audience; Two π-conjugated thienoisoindigo-based organic small molecules have been designed to be synthetically accessible through sustainable direct heteroarylation or Sonogashira C–C bond forming cross-coupling reactions utilizing a heterogeneous palladium catalyst. To access these materials, one molecule, TII-ThNaph2, contains a thiophene π-bridge to facilitate direct heteroarylation protocols, whereas the other, TII-AcNaph2, contains an acetylene π-bridge required for Sonogashira couplings. The synthetic route to both final materials was optimized to investigate the reactivity of thienoisoindigo, which to this point has not been significantly explored in comparison to other popular organic dyes such as diketopyrrolopyrrole and isoindigo. Considering the reported interest of thienoisoindigo-based materials in organic solar cells and field-effect transistors, both final materials have been characterized for their optical, electrochemical and thermal properties offering a comparison of the structure–property relationships that manifest as a result of the two different π-bridging units.

Details

Language :
English
ISSN :
21680485
Database :
OpenAIRE
Journal :
ACS Sustainable Chemistry & Engineering, ACS Sustainable Chemistry & Engineering, American Chemical Society, 2016, 4 (6), pp.3504-3517. ⟨10.1021/acssuschemeng.6b00554⟩
Accession number :
edsair.doi.dedup.....47ceb92ed8a6b2dc74e7ec083f2709bc
Full Text :
https://doi.org/10.1021/acssuschemeng.6b00554⟩