New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

Thomas Bura; Serge Beaupré; Olzhas A. Ibraikulov; Marc André Légaré; Jesse Quinn; Patrick Lévêque; Thomas Heiser; Yuning Li; Nicolas Leclerc; Mario Leclerc

doi:10.1021/acs.macromol.7b01198

New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

Thomas Bura, Serge Beaupré, Olzhas A. Ibraikulov, Marc André Légaré, Jesse Quinn, Patrick Lévêque, Thomas Heiser, Yuning Li, Nicolas Leclerc, Mario Leclerc

National Laboratory Astana

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

Abstract

Diketopyrrolopyrrole (DPP) derivatives are among the most efficient materials studied for both polymer solar cells (PSCs) and organic field-effect transistors (OFETs) applications. We report here the synthesis of new fluorinated dithienyldiketopyrrolopyrrole (fDT-DPP) monomers suitable for direct heteroarylation polymerization. fDT-DPP copolymers were then prepared to probe the effect of the fluorination. It was found that they feature deeper HOMO energy levels and smaller bandgaps than their non-fluorinated analogues. Moreover, some fDT-DPP copolymers show ambipolar behavior when tested in OFETs. For example, P2 shows hole mobility up to 0.8 cm² V^-1 s^-1 and electron mobility up to 0.5 cm² V^-1 s^-1. Inverted PSCs with power conversion efficiency (PCE) up to 7.5% were also obtained for P5. These results reported here (OFETs and PSCs) confirm that the fluorination of dithienyl-DPP moieties improves the performance of organic electronics devices. This study is also evidencing the strength of the direct heteroarylation polymerization and fDT-DPP as a new class of conjugated polymers.

Original language	English
Pages (from-to)	7080-7090
Number of pages	11
Journal	Macromolecules
Volume	50
Issue number	18
DOIs	https://doi.org/10.1021/acs.macromol.7b01198
Publication status	Published - Sep 26 2017

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics. / Bura, Thomas; Beaupré, Serge; Ibraikulov, Olzhas A.; Légaré, Marc André; Quinn, Jesse; Lévêque, Patrick; Heiser, Thomas; Li, Yuning; Leclerc, Nicolas; Leclerc, Mario.

In: Macromolecules, Vol. 50, No. 18, 26.09.2017, p. 7080-7090.

Research output: Contribution to journal › Article › peer-review

@article{15e79787dd6344289227add08526d665,

title = "New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics",

abstract = "Diketopyrrolopyrrole (DPP) derivatives are among the most efficient materials studied for both polymer solar cells (PSCs) and organic field-effect transistors (OFETs) applications. We report here the synthesis of new fluorinated dithienyldiketopyrrolopyrrole (fDT-DPP) monomers suitable for direct heteroarylation polymerization. fDT-DPP copolymers were then prepared to probe the effect of the fluorination. It was found that they feature deeper HOMO energy levels and smaller bandgaps than their non-fluorinated analogues. Moreover, some fDT-DPP copolymers show ambipolar behavior when tested in OFETs. For example, P2 shows hole mobility up to 0.8 cm2 V-1 s-1 and electron mobility up to 0.5 cm2 V-1 s-1. Inverted PSCs with power conversion efficiency (PCE) up to 7.5% were also obtained for P5. These results reported here (OFETs and PSCs) confirm that the fluorination of dithienyl-DPP moieties improves the performance of organic electronics devices. This study is also evidencing the strength of the direct heteroarylation polymerization and fDT-DPP as a new class of conjugated polymers.",

author = "Thomas Bura and Serge Beaupr{\'e} and Ibraikulov, {Olzhas A.} and L{\'e}gar{\'e}, {Marc Andr{\'e}} and Jesse Quinn and Patrick L{\'e}v{\^e}que and Thomas Heiser and Yuning Li and Nicolas Leclerc and Mario Leclerc",

note = "Funding Information: The authors acknowledge the Natural Sciences and Engineering Research Council of Canada (NSERC), Universit{\'e} Laval (APOG{\'E}E, Sentinelle Nord), the Canadian Institute for Advanced Research (CIFAR), and the European Fund for Regional Development (FEDER) within the framework of the program INTERREG V Rhin Supe{\'r} ieur and under the project no. 3.10 (PROOF) for their support. Compute Canada and Calcul Que{\'b} ec are also thanked for access to computational facilities. C. Roy is acknowledged for his help in the synthesis of some synthetic precursors. Publisher Copyright: {\textcopyright} 2017 American Chemical Society. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.",

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T1 - New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

AU - Bura, Thomas

AU - Beaupré, Serge

AU - Ibraikulov, Olzhas A.

AU - Légaré, Marc André

AU - Quinn, Jesse

AU - Lévêque, Patrick

AU - Heiser, Thomas

AU - Li, Yuning

AU - Leclerc, Nicolas

AU - Leclerc, Mario

N1 - Funding Information: The authors acknowledge the Natural Sciences and Engineering Research Council of Canada (NSERC), Université Laval (APOGÉE, Sentinelle Nord), the Canadian Institute for Advanced Research (CIFAR), and the European Fund for Regional Development (FEDER) within the framework of the program INTERREG V Rhin Supeŕ ieur and under the project no. 3.10 (PROOF) for their support. Compute Canada and Calcul Queb́ ec are also thanked for access to computational facilities. C. Roy is acknowledged for his help in the synthesis of some synthetic precursors. Publisher Copyright: © 2017 American Chemical Society. Copyright: Copyright 2017 Elsevier B.V., All rights reserved.

PY - 2017/9/26

Y1 - 2017/9/26

N2 - Diketopyrrolopyrrole (DPP) derivatives are among the most efficient materials studied for both polymer solar cells (PSCs) and organic field-effect transistors (OFETs) applications. We report here the synthesis of new fluorinated dithienyldiketopyrrolopyrrole (fDT-DPP) monomers suitable for direct heteroarylation polymerization. fDT-DPP copolymers were then prepared to probe the effect of the fluorination. It was found that they feature deeper HOMO energy levels and smaller bandgaps than their non-fluorinated analogues. Moreover, some fDT-DPP copolymers show ambipolar behavior when tested in OFETs. For example, P2 shows hole mobility up to 0.8 cm2 V-1 s-1 and electron mobility up to 0.5 cm2 V-1 s-1. Inverted PSCs with power conversion efficiency (PCE) up to 7.5% were also obtained for P5. These results reported here (OFETs and PSCs) confirm that the fluorination of dithienyl-DPP moieties improves the performance of organic electronics devices. This study is also evidencing the strength of the direct heteroarylation polymerization and fDT-DPP as a new class of conjugated polymers.

AB - Diketopyrrolopyrrole (DPP) derivatives are among the most efficient materials studied for both polymer solar cells (PSCs) and organic field-effect transistors (OFETs) applications. We report here the synthesis of new fluorinated dithienyldiketopyrrolopyrrole (fDT-DPP) monomers suitable for direct heteroarylation polymerization. fDT-DPP copolymers were then prepared to probe the effect of the fluorination. It was found that they feature deeper HOMO energy levels and smaller bandgaps than their non-fluorinated analogues. Moreover, some fDT-DPP copolymers show ambipolar behavior when tested in OFETs. For example, P2 shows hole mobility up to 0.8 cm2 V-1 s-1 and electron mobility up to 0.5 cm2 V-1 s-1. Inverted PSCs with power conversion efficiency (PCE) up to 7.5% were also obtained for P5. These results reported here (OFETs and PSCs) confirm that the fluorination of dithienyl-DPP moieties improves the performance of organic electronics devices. This study is also evidencing the strength of the direct heteroarylation polymerization and fDT-DPP as a new class of conjugated polymers.

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New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

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