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; Mihály Kállay; Gregor Scheipl; Franz Stelzer; Frank Wiesbrock

doi:10.1039/C2PY20219K

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

Elisabeth Rossegger,^a László Oláh,^a Roland Fischer,^b Petra Kaschnitz,^c Olívia Varga,^d Mihály Kállay,^d Gregor Scheipl,^e Franz Stelzer^c and Frank Wiesbrock*^c

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* Corresponding authors

^a Polymer Competence Center Leoben GmbH (PCCL), Roseggerstraße 12, 8700 Leoben, Austria

^b Graz University of Technology, Institute of Inorganic Chemistry, Stremayrgasse 9, 8010 Graz, Austria

^c Graz University of Technology, Institute for Chemistry and Technology of Materials, Stremayrgasse 9, 8010 Graz, Austria
E-mail: f.wiesbrock@tugraz.at
Fax: +43 316 873 10 32283
Tel: +43 316 873 32283

^d Budapest University of Technology and Economics (BME), Department of Physical Chemistry and Materials Science, P.O. Box 91, 1521 Budapest, Hungary

^e Joanneum Research, Materials Micro- and Nanostructuring, Leonhardstrasse 59, 8010 Graz, Austria

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.

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DOI: https://doi.org/10.1039/C2PY20219K
Article type: Paper
Submitted: 11 Apr 2012
Accepted: 14 Jul 2012
First published: 17 Jul 2012

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Polym. Chem., 2012,3, 2760-2767

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

E. Rossegger, L. Oláh, R. Fischer, P. Kaschnitz, O. Varga, M. Kállay, G. Scheipl, F. Stelzer and F. Wiesbrock, Polym. Chem., 2012, 3, 2760 DOI: 10.1039/C2PY20219K

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Polymer Chemistry

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

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

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