Polymers with Pendant Water‐Soluble Tetrafluorobenzene Sulfonic Acid Activated Esters: Synthesis, Stability, and Use for Glycopolymers in Water

Abstract

AbstractFunctional polymers can be synthesized via post‐polymerization modification with pendant‐activated ester groups on their backbones. There are, however, few reports on polymers bearing water‐soluble activated ester groups, as they are unstable in water. Herein, novel monomers and polymers bearing water‐soluble tetrafluorobenzene sulfonic acid (sulfoTFB) activated ester groups are reported. The corresponding sulfoTFB‐bearing polymers are successfully synthesized via controlled radical polymerization. The stabilities of the sulfoTFB‐bearing monomers and polymers are significantly improved by the introduction of an alkanediyl linker into sulfoTFB. The stability of sulfoTFB is found to be significantly improved when the linker is longer than a butanediyl linker, increasing in line with the length of the alkanediyl linker. The resulting sulfoTFB‐bearing polymer is used for synthesizing oligosaccharide‐grafted glycopolymers, which binds to lectin with high binding affinity, via post‐polymerization modification in water. This study thus details the preparation, investigation, and use of novel polymers with pendant water‐soluble sulfoTFB groups for post‐polymerization modification in water.