Triclocarban: Commercial Antibacterial and Highly Effective H-Bond Donating Catalyst for Ring-Opening Polymerization

Nayanthara U Dharmaratne; Jinal U Pothupitiya; Timothy J Bannin; Oleg I Kazakov; Matthew K Kiesewetter

doi:10.1021/acsmacrolett.7b00111

Triclocarban: Commercial Antibacterial and Highly Effective H-Bond Donating Catalyst for Ring-Opening Polymerization

ACS Macro Lett. 2017 Apr 18;6(4):421-425. doi: 10.1021/acsmacrolett.7b00111. Epub 2017 Mar 29.

Authors

Nayanthara U Dharmaratne¹, Jinal U Pothupitiya¹, Timothy J Bannin¹, Oleg I Kazakov¹, Matthew K Kiesewetter¹

Affiliation

¹ Department of Chemistry, University of Rhode Island, Kingston, Rhode Island 02881, United States.

PMID: 35610842
DOI: 10.1021/acsmacrolett.7b00111

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.