Work

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

Year: 2017

Type: article

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.

Source: ACS Macro Letters

DOI: 10.1021/acsmacrolett.7b00111

Authors: Nayanthara U. Dharmaratne, Jinal U. Pothupitiya, Timothy J. Bannin, Oleg I. Kazakov, Matthew K. Kiesewetter

Institution: University of Rhode Island

Language: English

Topic: biodegradable polymer synthesis and properties

Subfield: Biomaterials

Field: Materials Science

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, University of Rhode Island, Division of Chemistry

Award: G2656919733