Journal
MACROMOLECULES
Volume 49, Issue 3, Pages 774-780Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.macromol.6b00136
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Funding
- NIH under RI-INBRE [8 P20 GM103430-12]
- University of Rhode Island
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1531963] Funding Source: National Science Foundation
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For the first time, the controlled ring-opening polymerization (ROP) of epsilon-thionocaprolactone (tnCL) is conducted. The organocatalytic ROP of tnCL occurs without carbonyl scrambling, leading to homopoly(epsilon-thionocaprolactone) (PtnCL). The ROP by base catalysts alone is proposed to proceed via a nucleophilic mechanism, while the addition of an H-bond donating thiourea (TU) is shown to provide excellent reaction control. The increased reaction control provided by the TU occurs in the virtual absence of binding between tnCL and TU, and a mechanistic account for this observation is discussed. The monomer ring strain is measured and found to be similar to delta-valerolactone (VL). Copolymers with VL are synthesized, and the resulting analysis of the copolymer materials properties provides the only known physical characterizations of poly(thio(no)ester-co-ester)s.
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