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Covalent Immobilization of Antibacterial Furanones via Photochemical Activation of Perfluorophenylazide
KTH, School of Chemical Science and Engineering (CHE), Chemistry.ORCID iD: 0000-0003-1121-4007
2009 (English)In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 25, no 13, 7432-7437 p.Article in journal (Refereed) Published
Abstract [en]

N-(3-Trimethoxysilylpropyl)-4-azido-2,3,5,6-tetrafluorobenzamide (PFPA-silane) was used as a photoactive crosslinker to immobilize antibacterial furanone molecules on silicon oxide surfaces. This immobilization strategy is useful, especially for substrates and molecules that lack reactive functional groups. To this end, cleaned wafers were initially incubated in solutions of different concentrations of PFPA-silane to form a monolayer presenting azido groups on the surface. The functionalized surfaces were then treated with a furanone solution followed by illumination with UV light and extensive rinsing with ethanol to remove noncovalently adhered molecules, In the presented study, we demonstrate the ability to control the surface density of the immobilized furanone molecules by adjusting the concentration of PFPA-silane solution used for surface functionalization using complementary surface analytical techniques. The fluorine in PFPA-silane and the bromine in furanone molecules were convenient markers for the XPS study. The ellipsometric layer thickness of the immobilized furanone molecules on the surface decreased with decreasing PFPA-silane concentration, which correlated with a decline of water contact angle as a sign of film collapse. The intensity of characteristic azide vibration in the MTR IR spectra was monitored as a function of PFPA-silane concentration, and the peak disappeared completely after furanone application followed by UV irradiation. As a complementary technique to XPS, TOF-SIMS provided valuable information on the chemical and molecular structure of the modified surfaces and spatial distribution of the immobilized furanone molecules. Finally, this report presents a convenient, reproducible, and robust strategy to design antibacterial coating based on furanone compounds for applications in human health care.

Place, publisher, year, edition, pages
2009. Vol. 25, no 13, 7432-7437 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-77357DOI: 10.1021/la900334wISI: 000267533800043OAI: oai:DiVA.org:kth-77357DiVA: diva2:492015
Note
QC 20120210Available from: 2012-02-07 Created: 2012-02-06 Last updated: 2017-12-08Bibliographically approved

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