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

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

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Article number2324
JournalMolecules
Volume23
Issue number9
DOIs
Publication statusPublished - Sep 12 2018

Fingerprint

Nitriles
nitriles
Polymerization
Polymers
polymerization
polymers
Electrons
Bromine
Electronic equipment
Fluorine
electrons
Conjugated polymers
readers
bromine
electronics
fluorine
copolymers
Copolymers
Optical properties
Activation energy

Keywords

  • 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

Cite this

Theoretical calculations for highly selective direct heteroarylation polymerization : New nitrile-substituted dithienyl-diketopyrrolopyrrole-based polymers. / Bura, Thomas; Beaupré, Serge; Légaré, Marc André; Ibraikulov , Olzhas; Leclerc, Nicolas; Leclerc, Mario.

In: Molecules, Vol. 23, No. 9, 2324, 12.09.2018.

Research output: Contribution to journalArticle

Bura, Thomas ; Beaupré, Serge ; Légaré, Marc André ; Ibraikulov , Olzhas ; Leclerc, Nicolas ; Leclerc, Mario. / Theoretical calculations for highly selective direct heteroarylation polymerization : New nitrile-substituted dithienyl-diketopyrrolopyrrole-based polymers. In: Molecules. 2018 ; Vol. 23, No. 9.
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