Development of Novel Polymers Bearing Activated Esters for the Synthesis of Functional Polymers by

Abstract

Activated esters have been used in various fields including biochemistry and polymer chemistry because of their high reactivity and ease of reaction. In particular, the formation of amide bonds by the reaction of activated esters with amino groups has high synthetic chemical value due to its high selectivity and is used in the synthesis of many functional polymers. This review summarizes the recent development of novel polymers bearing activated esters for the synthesis of functional polymers by post-polymerization modification. The development of monomers and polymers bearing water-soluble active esters is described. In particular, the polymers bearing N-hydroxysulfosuccinimide（sulfoNHS）and 4-sulfo-2,3,5,6-tetrafluorophenyl（sulfoTFP）esters linked by an alkyl linker are useful for the post-polymerization modification in water because the watersoluble activated esters on the polymer are stable in water, while water-soluble activated esters are generally unstable and hydrolyzed in water. The sulfoNHS- or sulfoTFP-bearing polymers can be used in post-polymerization modification to synthesize glycopolymers in water. Post-polymerization dual modification onto a single functional group, such as thiolactone and azlactone, is interesting. Glycine propargyl ester is introduced as a novel activated ester on a polymer backbone. Azide-alkyne Huisgen cycloaddition with azide group and following amidation of glycine propargyl esters on a polymer backbone is described.