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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Thomas BuraMario Leclerc

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.

References

Dec 22, 2007·Journal of the American Chemical Society·Nicolas BlouinMario Leclerc
Dec 3, 2010·Chemical Communications : Chem Comm·Sabin-Lucian SuraruFrank Würthner
Apr 3, 2013·Accounts of Chemical Research·Lauren G Mercier, Mario Leclerc
Sep 24, 2013·Journal of the American Chemical Society·Il KangYun-Hi Kim
Nov 21, 2013·Physical Chemistry Chemical Physics : PCCP·Xiaorui LiuWei Shen
Aug 8, 2015·Chemical Reviews·Luyao LuLuping Yu
Dec 24, 2015·Accounts of Chemical Research·Weiwei LiRené A J Janssen
Jul 28, 2016·Journal of the American Chemical Society·Thomas BuraMario Leclerc
Nov 5, 2016·Chemical Reviews·Jean-Rémi PouliotMario Leclerc
Dec 31, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrea NittiDario Pasini
May 16, 2017·Macromolecular Chemistry and Physics·Ruurd HeuvelRené A J Janssen
May 18, 2017·Journal of the American Chemical Society·Wenchao ZhaoJianhui Hou
Mar 31, 2018·Advanced Materials·Shaoqing ZhangJianhui Hou

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Citations

May 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hui LiuShi-Yong Liu

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Methods Mentioned

BETA
differential scanning calorimetry
size exclusion chromatography
column chromatography

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