Journal
ACS MACRO LETTERS
Volume 6, Issue 4, Pages 421-425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsmacrolett.7b00111
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Funding
- NSF CAREER Award [CHE 1554830]
- University of Rhode Island
- NSF [1531963]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1531963] Funding Source: National Science Foundation
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The antibacterial compound, triclocarban (TCC), is shown to be a highly effective H-bond donating catalyst for ring-opening polymerization (ROP) when applied with an H-bond accepting base cocatalyst. These ROPs exhibit the characteristics of living polymerizations. TCC is shown to possess the high activity characteristic of urea (vs thiourea) H-bond donors. The urea class of H-bond donors is shown to remain highly active in H-bonding solvents, a trait that is not displayed by the corresponding thiourea H-bond donors. Two El bond donating ureas that are electronically similar to TCC are evaluated for their efficacy in ROP, and a mechanism of action is proposed. This off-the-shelf H-bond donor is among the most active and most controlled organocatalysts for the ROP of lactones.
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