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Title: Synthesis and Properties of Photoswitchable Carbohydrate Fluorosurfactants
Contributor(s): Hu, Yingxue (author); Marlow, Joshua B (author); Ramanathan, Rajesh (author); Zou, Wenyue (author); Tiew, Hui Geok (author); Pottage, Matthew J (author); Bansal, Vipul (author); Tabor, Rico F (author); Wilkinson, Brendan  (author)orcid 
Publication Date: 2015
DOI: 10.1071/CH15434
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Abstract: We describe the parallel synthesis, photocontrollable surface tension, and antibacterial performance of a new class of carbohydrate fluorosurfactant. Novel fluorosurfactants comprised a mono- or disaccharide head group linked to an azobenzene unit that was variably substituted with a trifluoromethyl group. Fluorosurfactants were rapidly assembled using the venerable CuI-catalysed azide-alkyne cycloaddition reaction and exhibited light-addressable surface activity, excellent water solubility, and selective antibacterial activity against Gram-positive 'Staphylococcus aureus'. Notably, the physicochemical and biological activity of these novel materials was heavily dependent on the nature of the head group and the position of the trifluoromethyl substituent on the azobenzene ring. The UV-adapted 'cis'-isomer of fluorosurfactants displayed good thermal stability at ambient temperature, with little reversion to the stable 'trans' isomer after 16 h. These novel, light-responsive materials should find broad interest in a range of biomedical and technological fields, including drug and gene delivery, self-cleaning oleophobic surfaces, and antibacterial coatings for medical devices.
Publication Type: Journal Article
Grant Details: ARC/DE130101673
Source of Publication: Australian Journal of Chemistry, 68(12), p. 1880-1884
Publisher: CSIRO Publishing
Place of Publication: Australia
ISSN: 0004-9425
Field of Research (FOR): 030503 Organic Chemical Synthesis
030603 Colloid and Surface Chemistry
030401 Biologically Active Molecules
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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