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Issue 10, 2012
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Furan containing diketopyrrolopyrrolecopolymers: synthesis, characterization, organic field effect transistor performance and photovoltaic properties

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Abstract

In this work, we report design, synthesis and characterization of solution processable low band gap polymer semiconductors, poly{3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-phenylene} (PDPP-FPF), poly{3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-naphthalene} (PDPP-FNF) and poly{3,6-difuran-2-yl-2,5-di(2-octyldodecyl)-pyrrolo[3,4-c]pyrrole-1,4-dione-alt-anthracene} (PDPP-FAF) using the furan-containing 3,6-di(furan-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DBF) building block. As DBF acts as an acceptor moiety, a series of donor–acceptor (D–A) copolymers can be generated when it is attached alternatively with phenylene, naphthalene or anthracene donor comonomer blocks. Optical and electrochemical characterization of thin films of these polymers reveals band gaps in the range of 1.55–1.64 eV. These polymers exhibit excellent hole mobility when used as the active layer in organic thin-film transistor (OTFT) devices. Among the series, the highest hole mobility of 0.11 cm2 V−1 s−1 is achieved in bottom gate and top-contact OTFT devices using PDPP-FNF. When these polymers are used as a donor and [70]PCBM as the acceptor in organic photovoltaic (OPV) devices, power conversion efficiencies (PCE) of 2.5 and 2.6% are obtained for PDPP-FAF and PDPP-FNFpolymers, respectively. Such mobility values in OTFTs and performance in OPV make furan-containing DBF a very promising block for designing new polymer semiconductors for a wide range of organic electronic applications.

Graphical abstract: Furan containing diketopyrrolopyrrole copolymers: synthesis, characterization, organic field effect transistor performance and photovoltaic properties

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Article information


Submitted
04 Oct 2011
Accepted
23 Nov 2011
First published
23 Dec 2011

J. Mater. Chem., 2012,22, 4425-4435
Article type
Paper

Furan containing diketopyrrolopyrrole copolymers: synthesis, characterization, organic field effect transistor performance and photovoltaic properties

P. Sonar, S. P. Singh, E. L. Williams, Y. Li, M. S. Soh and A. Dodabalapur, J. Mater. Chem., 2012, 22, 4425
DOI: 10.1039/C2JM14989C

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