Exploiting α-benzylated 1,4-butanesultones to expedite the discovery of small-molecule, LCST-type sulfobetaine zwitterionic materials

Abstract

Herein, we report both the concise synthesis and discovery of a small library of 16 sulfobetaine-like zwitterionic materials (ZMs) that exhibit LCST phase transitions in water and their structural optimization to further fine-tune the polarity of the benzyl substituent on the α-position of the sulfonate moiety. Ultimately, we achieved the preparation of novel ZMs carrying attractive T_c values, which demonstrated the real value of the structural tunability of these ZMs. Furthermore, we present a proof-of-concept application for the analysis of biomolecules. To the best of our knowledge, this is the first report on sulfobetaine-substituted ZMs as small-molecule smart materials exhibiting LCST property and their miscibility/immiscibility with water triggered by temperature are entirely switchable and reversible.