Dithienopyrrole-quinoxaline/pyridopyrazine donor-acceptor polymers: Synthesis and electrochemical, optical, charge-transport, and photovoltaic properties

Xuan Zhang, Jae Won Shim, Shree Prakash Tiwari, Qing Zhang, Joseph E. Norton, Pei Tzu Wu, Stephen Barlow, Samson A. Jenekhe, Bernard Kippelen, Jean Luc Brédas, Seth R. Marder

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

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-1 s -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-I h)[5,6]fullerene-3′-butanoic acid methyl ester (1:3 weight ratio) exhibited average power conversion efficiencies up to 1.4%.

Original languageEnglish (US)
Pages (from-to)4971-4982
Number of pages12
JournalJournal of Materials Chemistry
Volume21
Issue number13
DOIs
StatePublished - Apr 7 2011
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry

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