Theoretical calculations for highly selective direct heteroarylation polymerization: New nitrile-substituted dithienyl-diketopyrrolopyrrole-based polymers

Thomas Bura, Serge Beaupré, Marc André Légaré, Olzhas A. Ibraikulov, Nicolas Leclerc, Mario Leclerc

Research output: Contribution to journalArticle

3 Citations (Scopus)


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.

Original languageEnglish
Article number2324
Issue number9
Publication statusPublished - Sep 12 2018



  • Conjugated polymers
  • DHAP
  • Organic electronics
  • Selectivity
  • Theoretical calculations

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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