Journal
MACROMOLECULES
Volume 48, Issue 16, Pages 5481-5486Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.macromol.5b01463
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Funding
- NIH under RI-INBRE [8 P20 GM103430-12]
- University of Rhode Island
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Organocatalysts typically used for the ring-opening polymerization (ROP) of cyclic ester monomers are applied to a thiolactone, epsilon-thiocaprolactone (tCL). In the absence of an H-bond donor, a nucleophilic polymerization mechanism is proposed. Despite the decreased ability of thioesters and thiols (versus esters and alcohols) to H-bond, H-bonding organocatalysts-a thiourea in combination with an H-bond accepting base-are also effective for the ROP of tCL. The increased nucleophilicity of thiols (versus alcohols) is implicated in the increased M-w/M-n of the poly(thiocaprolactone) versus poly(caprolactone), but deleterious transesterification is suppressed in the presence of a thiourea. The thioester monomer, tCL, is shown to be thermodynamically similar to epsilon-caprolactam but kinetically similar to epsilon-caprolactone.
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