Bifunctional Fluoroalcohol Catalysts Enabled Sustainable Synthesis of Poly(amino acid)s†. Issue 8 (8th June 2021)

• Record Type: Journal Article
• Authors: He, Wenjing; Tao, Youhua
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 8(2021)
• Page Start: 2119
• Page End: 2124
• Publication Date: 2021-06-08
• Subjects: Bifunctional -- Organocatalyst -- Fluoroalcohol -- Amino acid -- Polymerization; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202100205
• Languages: English
• ISSNs: 1001-604X

Abstract

Main observation and conclusion: A series of novel bifunctional single‐molecule hydrogen‐bonding organocatalysts based on fluorinated tertiary alcohol were synthesized to mediate the metal‐free polymerization of α ‐amino acid N ‐carboxyanhydride (NCA) monomer. Through the screening of catalysts, the polymerization catalyzed by the preferred bifunctional fluoroalcohol catalyst proceeded in a fast and controlled manner, affording high molecular weight polypeptide up to 35.2 × 10 4 Da with relatively narrow molecular weight distribution ( Đ < 1.20). A phenomenon of self‐accelerating effect of polymerization induced by α ‐helical structure of polypeptides was observed, and a possible polymerization pathway has been discussed. Abstract : A novel bifunctional single‐molecule hydrogen‐bonding organocatalyst based on fluorinated tertiary alcohols was designed to mediate the metal‐free polymerization of α ‐amino acid N ‐carboxyanhydride monomer.