Critical role of side-chain attachment density on the order and device performance of polythiophenes

R. Joseph Kline, Dean M. DeLongchamp, Daniel A. Fischer, Eric K. Lin, Lee J. Richter, Michael L. Chabinyc, Michael F. Toney, Martin Heeney, Iain McCulloch

Research output: Contribution to journalArticlepeer-review

321 Scopus citations


High performance, solution processable semiconductors are critical to the realization of low cost, large area electronics. We show that a signature molecular packing motif-side-chain interdigitation-correlates to high performance for a large and important class of organic semiconductors. The side chains of recently developed high performance copolymers of poly(alkylthiophenes) can and do interdigitate substantially, whereas they do not in the most common form of the extensively studied, lower performance poly (alky thiophenes). Sidechain interdigitation provides a mechanism for three-dimensional ordering; without it, poly(alkylthiophenes) are limited to small domains and poor performance. We propose the synthetic design rule that three-dimensional ordering is promoted by side-chain attachment densities sufficiently low to permit interdigitation.

Original languageEnglish (US)
Pages (from-to)7960-7965
Number of pages6
Issue number22
StatePublished - Oct 30 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry


Dive into the research topics of 'Critical role of side-chain attachment density on the order and device performance of polythiophenes'. Together they form a unique fingerprint.

Cite this