Norbornenyl-substituted thiophenes and terthiophenes: novel doubly polymerizable monomers

Keith J. Watson, Patrick S. Wolfe, Son Binh T. Nguyen, Jin Zhu, Chad A. Mirkin

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The synthesis and polymerization of norbornenyl-substituted thiophenes (2 and 4) and terthiophenes (3 and 5) are reported. All monomers readily undergo ring-opening metathesis polymerization (ROMP) using the ruthenium catalyst, Cl2(PPCy3)2 Ru=CHPh (1). The terthienyl monomers 3 and 5 were directly polymerized onto the surface of a gold electrode via electrochemical oxidation of the capping terthienyl units, while the direct electrochemical homopolymerization of 2 was not achievable, which is consistent with previous literature reports for similarly substituted thiophenes. Chemical polymerization of the terthienyl segments of 3 and 5 using FeCl3 yielded insoluble materials. Finally, polymers obtained from the ROMP procedure were further cross-linked using the oxidative techniques described above, yielding highly networked materials which displayed an increase in thermal stability and electrical conductivity relative to their single-chain polymeric precursors.

Original languageEnglish (US)
Pages (from-to)4628-4633
Number of pages6
JournalMacromolecules
Volume33
Issue number13
DOIs
StatePublished - Jun 27 2000

ASJC Scopus subject areas

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

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