Synthesis and properties of photoswitchable carbohydrate fluorosurfactants

Yingxue Hu, Joshua Marlow, Rajesh Ramanathan, Wenyue Zou, Hui Geok Tiew, Matthew Pottage, Vipul Bansal, Richard Francis Tabor, Brendan Wilkinson

Research output: Contribution to journalArticleResearchpeer-review

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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 16h. 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.
Original languageEnglish
Pages (from-to)1880-1884
Number of pages5
JournalAustralian Journal of Chemistry
Volume68
Issue number12
DOIs
Publication statusPublished - 2015

Cite this

Hu, Y., Marlow, J., Ramanathan, R., Zou, W., Tiew, H. G., Pottage, M., ... Wilkinson, B. (2015). Synthesis and properties of photoswitchable carbohydrate fluorosurfactants. Australian Journal of Chemistry, 68(12), 1880-1884. https://doi.org/10.1071/CH15434
Hu, Yingxue ; Marlow, Joshua ; Ramanathan, Rajesh ; Zou, Wenyue ; Tiew, Hui Geok ; Pottage, Matthew ; Bansal, Vipul ; Tabor, Richard Francis ; Wilkinson, Brendan. / Synthesis and properties of photoswitchable carbohydrate fluorosurfactants. In: Australian Journal of Chemistry. 2015 ; Vol. 68, No. 12. pp. 1880-1884.
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Hu, Y, Marlow, J, Ramanathan, R, Zou, W, Tiew, HG, Pottage, M, Bansal, V, Tabor, RF & Wilkinson, B 2015, 'Synthesis and properties of photoswitchable carbohydrate fluorosurfactants', Australian Journal of Chemistry, vol. 68, no. 12, pp. 1880-1884. https://doi.org/10.1071/CH15434

Synthesis and properties of photoswitchable carbohydrate fluorosurfactants. / Hu, Yingxue; Marlow, Joshua; Ramanathan, Rajesh; Zou, Wenyue; Tiew, Hui Geok; Pottage, Matthew; Bansal, Vipul; Tabor, Richard Francis; Wilkinson, Brendan.

In: Australian Journal of Chemistry, Vol. 68, No. 12, 2015, p. 1880-1884.

Research output: Contribution to journalArticleResearchpeer-review

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