Triclocarban: Commercial Antibacterial and Highly Effective H-Bond Donating Catalyst for Ring-Opening Polymerization
Date of Original Version
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.
ACS Macro Letters
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.