Regiochemistry of poly(3-hexylthiophene): Synthesis and investigation of a conducting polymer

Ted M. Pappenfus, David L. Hermanson, Stuart G. Kohl, Jacob H. Melby, Laura M. Thoma, Nancy E. Carpenter, Demetrio A. Da Silva Filho, Jean-Luc Bredas

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

Abstract

A series of experiments for undergraduate laboratory courses (e.g., organic, polymer, inorganic) have been developed. These experiments focus on understanding the regiochemistry of the conducting polymer poly(3- hexylthiophene) (P3HT). The substitution patterns in P3HTs control their conformational features, which, in turn, dictates the p conjugation and subsequent electronic properties of the materials. The regiochemistry in P3HTs can be controlled synthetically, and this experiment includes the synthesis of regioregular P3HT via Grignard metathesis chemistry. The regiochemistry is established unambiguously using techniques such as 1H NMR and UV-vis spectroscopy;comparisons to the regiorandom isomer are then made. Density functional theory calculations are also used to shed light on the electronic and conformational features of the polymers by analyzing suitable oligomers. These experiments illustrate the importance of regiochemistry in organic materials and expose students to a number of important chemical concepts as well as useful physical and theoretical methods.

Original languageEnglish (US)
Pages (from-to)522-525
Number of pages4
JournalJournal Of Chemical Education
Volume87
Issue number5
DOIs
StatePublished - Aug 27 2010

Keywords

  • Catalysis
  • Computational chemistry
  • Grignard reagents
  • Hands-on learning/manipulatives
  • Heterocycles
  • Inorganic chemistry
  • Inquiry-based/discovery learning
  • Laboratory instruction
  • NMR spectroscopy
  • Organic chemistry
  • Organometallics
  • Polymer chemistry
  • Second-year undergraduate
  • Synthesis
  • UV-vis spectroscopy
  • Upper-division undergraduate

ASJC Scopus subject areas

  • Chemistry(all)
  • Education

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