Get access

Microwave-assisted TCNE/TCNQ addition to poly(thienyleneethynylene) derivative for construction of donor–acceptor chromophores

Authors

  • Yuping Yuan,

    1. Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
    Search for more papers by this author
  • Tsuyoshi Michinobu,

    Corresponding author
    1. Global Edge Institute, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan
    2. PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama, Japan
    • Global Edge of Institute, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan
    Search for more papers by this author
  • Minoru Ashizawa,

    1. Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
    Search for more papers by this author
  • Takehiko Mori

    1. Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
    Search for more papers by this author

Abstract

The alkyne moieties of poly(3-hexylthienyleneethynylene) were reacted with tetracyanoethylene or 7,7,8,8-tetracyanoquinodimethane by microwave irradiation to produce donor–acceptor chromophores in the polymer main chain. The resulting polymers were fully characterized by GPC, 1H NMR, and IR spectroscopies, and elemental analyses. They were both thermally and chemically stable, as revealed by thermogravimetric analyses and ESR measurements. UV–vis-NIR spectroscopy revealed charge-transfer bands in the low-energy region, and electrochemistry confirmed the narrower band gaps with the elevated HOMO and lower LUMO levels relative to the precursor polymer. To take advantage of these postfunctionalization methods, p-type doping of the polymers with I2 was attempted. Room temperature conductivities of the postfunctionalized polymers reached 4.5 × 10−5 S cm−1, which was about 10 times greater than that of the precursor polymer. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

Get access to the full text of this article

Ancillary