Chiral Polymers from Norbornenes Based on Renewable Chemical Feedstocks.

Content Provider	Europe PMC
Author	Nazarov, Ivan V. Zarezin, Danil P. Solomatov, Ivan A. Danshina, Anastasya A. Nelyubina, Yulia V. Ilyasov, Igor R. Bermeshev, Maxim V.
Editor	Iordanskii, Alexey Lotti, Nadia Siracusa, Valentina Soccio, Michelina
Copyright Year	2022
Abstract	Optically active polymers are of great interest as materials for dense enantioselective membranes, as well as chiral stationary phases for gas and liquid chromatography. Combining the versatility of norbornene chemistry and the advantages of chiral natural terpenes in one molecule will open up a facile route toward the synthesis of diverse optically active polymers. Herein, we prepared a set of new chiral monomers from cis-5-norbornene-2,3-dicarboxylic anhydride and chiral alcohols of various natures. Alcohols based on cyclic terpenes ((-)-menthol, (-)-borneol and pinanol), as well as commercially available alcohols (S-(-)-2-methylbutanol-1, S-(+)-3-octanol), were used. All the synthesized monomers were successfully involved in ring-opening metathesis polymerization, affording polymers in high yields (up to 96%) and with molecular weights in the range of 1.9 × 105–5.8 × 105 (Mw). The properties of the metathesis polymers obtained were studied by TGA and DSC analysis, WAXD, and circular dichroism spectroscopy. The polymers exhibited high thermal stability and good film-forming properties. Glass transition temperatures for the prepared polymers varied from −30 °C to +139 °C and, therefore, the state of the polymers changed from rubbery to glassy. The prepared polymers represent a new attractive platform of chiral polymeric materials for enantioselective membrane separation and chiral stationary phases for chromatography.
Journal	Polymers
Volume Number	14
PubMed Central reference number	PMC9786787
Issue Number	24
PubMed reference number	36559820
e-ISSN	20734360
DOI	10.3390/polym14245453
Language	English
Publisher	MDPI
Publisher Date	2022-12-13
Access Restriction	Open
Rights License	Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). © 2022 by the authors.
Subject Keyword	chiral polymer renewable feedstock pinene menthol borneol norbornene polynorbornene ring-opening metathesis polymerization
Content Type	Text
Resource Type	Article
Subject	Chemistry Polymers and Plastics