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Bielawski, Christopher W.
Synthetic Materials & Macromolecules
Research Interests
  • Synthetic chemistry, materials science, polymer chemistry, catalysis, carbon-based materials

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A systematic study of stereochemical effects in homologous poly(alkenamer)s: Dewar benzene versus norbornene

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Title
A systematic study of stereochemical effects in homologous poly(alkenamer)s: Dewar benzene versus norbornene
Author
Lee, Stanfield Y.Seo, JinwonBielawski, Christopher W.
Issue Date
2020-06
Publisher
WILEY
Citation
JOURNAL OF POLYMER SCIENCE, v.58, no.12, pp.1687 - 1698
Abstract
Two diastereomeric derivatives of norbornene, dimethyl (1R,2R,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate and dimethyl (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate, were synthesized and polymerized using ring-opening metathesis polymerization (ROMP). For comparative purposes, diastereomeric derivatives of Dewar benzene, dimethyl (1R,2S,3R,4S)-bicyclo[2.2.0]hex-5-ene-2,3-dicarboxylate and dimethyl (1R,2S,3S,4S)-bicyclo[2.2.0]hex-5-ene-2,3-dicarboxylate, were also synthesized and polymerized using ROMP. The polymerization reactions proceeded in a controlled manner as evidenced in part by linear relationships between the monomer-to-catalyst feed ratios and the molecular weights of the polymer products. Chain extension experiments were also conducted which facilitated the formation of block copolymers. Although the poly(norbornene) derivatives exhibited glass transition temperatures that were dependent on their monomer stereochemistry (cis: 115 degrees C vs. trans: 125 degrees C), more pronounced differences were observed upon analysis of the polymers derived from Dewar benzene (cis: 70 degrees C vs. trans: 95 degrees C). Likewise, microphase separation was observed in block copolymers that were prepared using the diastereomeric monomers derived from Dewar benzene but not in block copolymers of the norbornene-based diastereomers. The differential thermal properties were attributed to the relative monomer sizes as reducing the distances between the polymer backbones and the pendant stereocenters appeared to enhance the thermal effects.
URI
https://scholarworks.unist.ac.kr/handle/201301/49129
URL
https://onlinelibrary.wiley.com/doi/full/10.1002/pol.20200250
DOI
10.1002/pol.20200250
ISSN
2642-4150
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