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Molecules 2018, 23(9), 2324; https://doi.org/10.3390/molecules23092324

Theoretical Calculations for Highly Selective Direct Heteroarylation Polymerization: New Nitrile-Substituted Dithienyl-Diketopyrrolopyrrole-Based Polymers

1
Canada Research Chair on Electroactive and Photoactive Polymers, Department of Chemistry, Université Laval, Quebec City, QC G1V 0A6, Canada
2
Institut für Anorganische Chemie, Julius-Maximilians Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
3
Laboratoire ICube, DESSP, Université de Strasbourg, CNRS, 23 rue du Loess, 67037 Strasbourg, France
4
Institut de Chimie et Procédés pour l’Énergie, l’Environnement et la Santé, ICPEES, Université de Strasbourg, CNRS, 67087 Strasbourg, France
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editors: Roman Dembinski and Derek J. McPhee
Received: 3 August 2018 / Revised: 7 September 2018 / Accepted: 11 September 2018 / Published: 12 September 2018
(This article belongs to the Special Issue Direct (Hetero)Arylation: A New Tool for Organic Electronics)
Full-Text   |   PDF [4682 KB, uploaded 12 September 2018]   |  

Abstract

Direct Heteroarylation Polymerization (DHAP) is becoming a valuable alternative to classical polymerization methods being used to synthesize π-conjugated polymers for organic electronics applications. In previous work, we showed that theoretical calculations on activation energy (Ea) of the C–H bonds were helpful to rationalize and predict the selectivity of the DHAP. For readers’ convenience, we have gathered in this work all our previous theoretical calculations on Ea and performed new ones. Those theoretical calculations cover now most of the widely utilized electron-rich and electron-poor moieties studied in organic electronics like dithienyl-diketopyrrolopyrrole (DT-DPP) derivatives. Theoretical calculations reported herein show strong modulation of the Ea of C–H bond on DT-DPP when a bromine atom or strong electron withdrawing groups (such as fluorine or nitrile) are added to the thienyl moiety. Based on those theoretical calculations, new cyanated dithienyl-diketopyrrolopyrrole (CNDT-DPP) monomers and copolymers were prepared by DHAP and their electro-optical properties were compared with their non-fluorinated and fluorinated analogues. View Full-Text
Keywords: DHAP; selectivity; theoretical calculations; conjugated polymers; organic electronics DHAP; selectivity; theoretical calculations; conjugated polymers; organic electronics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Bura, T.; Beaupré, S.; Légaré, M.-A.; Ibraikulov, O.A.; Leclerc, N.; Leclerc, M. Theoretical Calculations for Highly Selective Direct Heteroarylation Polymerization: New Nitrile-Substituted Dithienyl-Diketopyrrolopyrrole-Based Polymers. Molecules 2018, 23, 2324.

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