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Issue 10, 2012
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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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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.

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

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Publication details

The article was received on 11 Apr 2012, accepted on 14 Jul 2012 and first published on 17 Jul 2012


Article type: Paper
DOI: 10.1039/C2PY20219K
Citation: 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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