Synthesis and Properties of Photoswitchable Carbohydrate Fluorosurfactants

• DOI: 10.1071/ch15434
• Publication Date: 2015-08-17T00:21:00Z
• Authors: Yingxue Hu; Joshua B. Marlow; Rajesh Ramanathan; Wenyue Zou; Hui Geok Tiew; Matthew J. Pottage; Vipul Bansal; Rico F. Tabor; Brendan L. Wilkinson
• Keywords: Azobenzene; Biocatalysis

We describe the parallel synthesis, photocontrollable surface tension, and antibacterial performance of a new class carbohydrate fluorosurfactant. Novel fluorosurfactants comprised mono- or disaccharide head group linked to an azobenzene unit that was variably substituted with trifluoromethyl group. Fluorosurfactants were rapidly assembled using venerable CuI-catalysed azide–alkyne cycloaddition reaction exhibited light-addressable activity, excellent water solubility, selective activity against Gram-positive Staphylococcus aureus. Notably, physicochemical biological these novel materials heavily dependent on nature position substituent ring. The UV-adapted cis-isomer displayed good thermal stability at ambient temperature, little reversion stable trans isomer after 16 h. These novel, light-responsive should find broad interest in range biomedical technological fields, including drug gene delivery, self-cleaning oleophobic surfaces, coatings for medical devices.