Alkylated Selenophene-Based Ladder-Type Monomers via a Facile Route for High-Performance Thin-Film Transistor Applications

Zhuping Fei, Yang Han, Eliot Gann, Thomas Hodsden, Anthony S. R. Chesman, Christopher R. McNeill, Thomas D Anthopoulos, Martin Heeney

Research output: Contribution to journalArticleResearchpeer-review

52 Citations (Scopus)

Abstract

We report the synthesis of two new selenophene-containing ladder-type monomers, cyclopentadiselenophene (CPDS) and indacenodiselenophene (IDSe), via a 2-fold and 4-fold Pd-catalyzed coupling with a 1,1-diborylmethane derivative. Copolymers with benzothiadiazole were prepared in high yield by Suzuki polymerization to afford materials which exhibited excellent solubility in a range of nonchlorinated solvents. The CPDS copolymer exhibited a band gap of just 1.18 eV, which is among the lowest reported for donor-acceptor polymers. Thin-film transistors were fabricated using environmentally benign, nonchlorinated solvents, with the CPDS and IDSe copolymers exhibiting hole mobility up to 0.15 and 6.4 cm2 V-1 s-1, respectively. This high performance was achieved without the undesirable peak in mobility often observed at low gate voltages due to parasitic contact resistance.

Original languageEnglish
Pages (from-to)8552-8561
Number of pages10
JournalJournal of the American Chemical Society
Volume139
Issue number25
DOIs
Publication statusPublished - 28 Jun 2017

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