Synthesis of a poly(2-azanorbornene) with a high degree of cis-TT-stereoregularity and a regular secondary solution structure

Elisabeth Rossegger, László Oláh, Roland Fischer, Petra Kaschnitz, Olívia Varga, M. Kállay, Gregor Scheipl, Franz Stelzer, Frank Wiesbrock

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5 Citations (Scopus)

Abstract

Methyl-N-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (AzaN) was synthesized as a diastereomerically pure monomer and subsequently polymerized with the ruthenium-based M31® catalyst. The poly(2- azanorbornene)s with polymerization degrees in the range from 100 to 300 exhibited high degrees of cis-TT stereoregularity in contrast to previously reported poly(2-azanorbornene)s that were prepared with molybdenum-based catalysts and exhibited cis-HT and trans-HT stereoregularity. The formation of regular secondary structures in acetonitrile solution was verified by circular dichroism and AFM measurements and supported by theoretical calculations of a polymer model with eight repeating units. Of special note are the large diameters of the secondary structures that are indicative of a multiple-strand filament.

Original languageEnglish
Pages (from-to)2760-2767
Number of pages8
JournalPolymer Chemistry
Volume3
Issue number10
DOIs
Publication statusPublished - 2012

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Biochemistry
  • Biomedical Engineering
  • Bioengineering

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    Rossegger, E., Oláh, L., Fischer, R., Kaschnitz, P., Varga, O., Kállay, M., Scheipl, G., Stelzer, F., & Wiesbrock, F. (2012). Synthesis of a poly(2-azanorbornene) with a high degree of cis-TT-stereoregularity and a regular secondary solution structure. Polymer Chemistry, 3(10), 2760-2767. https://doi.org/10.1039/c2py20219k