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Polar Thermoplastics with Tunable Physical Properties Enabled by the Stereoregular Copolymerization of Vinyl Ethers

preprint
submitted on 25.09.2019 and posted on 27.09.2019 by Aaron Teator, Travis Varner, Paige Jacky, Karolina Sheyko, Frank Leibfarth
A series of isotactic, semicrystalline vinyl ether copolymers (up to 94% meso diads) were synthesized using a chiral BINOL-based phosphoric acid in combination with a titanium Lewis acid. This stereoselective cationic polymerization enabled the systematic tuning of both glass-transition (Tg) and melting temperature (Tm) in copolymers derived from alkyl vinyl ethers (i.e., ethyl, butyl, isobutyl). Additionally, a vinyl ether comonomer bearing an acyl-protected alcohol was utilized as a platform for post-functionalization. Copolymers containing the masked alcohols were shown to undergo facile deprotection and subsequent coupling with a desired acid chloride. Collectively, these results highlight the diverse material properties and expanded chemical space accessible through stereoselective cationic polymerization mediated by a chiral anion.

Funding

NSF CAREER Award (CHE-1847362)

History

Email Address of Submitting Author

FrankL@email.unc.edu

Institution

University of North Carolina at Chapel Hill

Country

United States

ORCID For Submitting Author

0000-0001-7737-0331

Declaration of Conflict of Interest

No conflict of interest

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