Synthesis and Properties of Photoswitchable Carbohydrate Fluorosurfactants

Title
Synthesis and Properties of Photoswitchable Carbohydrate Fluorosurfactants
Publication Date
2015
Author(s)
Hu, Yingxue
Marlow, Joshua B
Ramanathan, Rajesh
Zou, Wenyue
Tiew, Hui Geok
Pottage, Matthew J
Bansal, Vipul
Tabor, Rico F
Wilkinson, Brendan
( author )
OrcID: https://orcid.org/0000-0003-1866-6540
Email: bwilkin7@une.edu.au
UNE Id une-id:bwilkin7
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
CSIRO Publishing
Place of publication
Australia
DOI
10.1071/CH15434
UNE publication id
une:20886
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.
Link
Citation
Australian Journal of Chemistry, 68(12), p. 1880-1884
ISSN
1445-0038
0004-9425
Start page
1880
End page
1884

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