Triclocarban: Commercial Antibacterial and Highly Effective H-Bond Donating Catalyst for Ring-Opening Polymerization
Document Type
Article
Date of Original Version
4-18-2017
Abstract
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 H-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.
Publication Title, e.g., Journal
ACS Macro Letters
Volume
6
Issue
4
Citation/Publisher Attribution
Dharmaratne, Nayanthara U., Jinal U. Pothupitiya, Timothy J. Bannin, Oleg I. Kazakov, and Matthew K. Kiesewetter. "Triclocarban: Commercial Antibacterial and Highly Effective H-Bond Donating Catalyst for Ring-Opening Polymerization." ACS Macro Letters 6, 4 (2017): 421-425. doi: 10.1021/acsmacrolett.7b00111.