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Issue 13, 2011
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Dithienopyrrolequinoxaline/pyridopyrazine donor–acceptor polymers: synthesis and electrochemical, optical, charge-transport, and photovoltaic properties

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Abstract

Soluble alternating copolymers of N-(3,4,5-tri-n-dodecyloxyphenyl)dithieno[3,2-b:2′,3′-d]pyrrole donor groups and 2,3-di-n-decylquinoxaline, 2,3-di-n-decylpyrido[3,4-b]pyrazine, 2,3,6,7-tetrakis(n-decyloxy)benzo[a,c]phenazine, or 2,3,6,7-tetrakis(n-decyloxy)dibenzo[f,h]pyrido[4,3-b]quinoxaline acceptors were synthesised using Stille coupling reactions. Experimental absorption maxima in THF range from 645 to 770 nm. These optical data, along with the results of quantum-chemical calculations and electrochemical measurements, show that, as expected, the pyridopyrazine moiety acts as a stronger acceptor than quinoxaline and that the extended species benzophenazine and dibenzopyridoquinoxaline are stronger acceptors than quinoxaline and pyridopyrazine, respectively. Modest average hole mobilities of up to ca. 3.0 × 10−4 cm2 V−1s−1 were obtained in field-effect transistors. Bulk heterojunction photovoltaic devices made from blends of the benzo[a,c]phenazine-based polymer with 3′-phenyl-3′H-cyclopropa[1,9](C60-Ih)[5,6]fullerene-3′-butanoic acid methyl ester (1 : 3 weight ratio) exhibited average power conversion efficiencies up to 1.4%.

Graphical abstract: Dithienopyrrole–quinoxaline/pyridopyrazine donor–acceptor polymers: synthesis and electrochemical, optical, charge-transport, and photovoltaic properties

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Publication details

The article was received on 08 Dec 2010, accepted on 21 Jan 2011 and first published on 17 Feb 2011


Article type: Paper
DOI: 10.1039/C0JM04290K
Citation: J. Mater. Chem., 2011,21, 4971-4982
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    Dithienopyrrolequinoxaline/pyridopyrazine donor–acceptor polymers: synthesis and electrochemical, optical, charge-transport, and photovoltaic properties

    X. Zhang, J. W. Shim, S. P. Tiwari, Q. Zhang, J. E. Norton, P. Wu, S. Barlow, S. A. Jenekhe, B. Kippelen, J. Brédas and S. R. Marder, J. Mater. Chem., 2011, 21, 4971
    DOI: 10.1039/C0JM04290K

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