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Issue 2, 2016
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Fluorescence quenching in β-cyclodextrin vesicles: membrane confinement and host–guest interactions

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Abstract

Fluorescent β-cyclodextrin vesicles (β-CDV) that display host cavities available for host–guest interactions at the vesicle surface were prepared by incorporation of the hydrophobic spirobifluorene-based dye 1 into the membrane of unilamellar vesicles. Fluorescence quenching of dye 1 was observed in the presence of different quenchers. Methyl viologen 2 does not quench dye 1 because it does not bind to β-CDV. 4-Nitrophenol 3 and 4-nitrophenol covalently connected to adamantane 4 quench the fluorescence of dye 1 in neutral solution, but by different mechanisms according to lifetime measurements. The quenching efficiency of 3 is pH dependent due to the presence of the phenolate form. Competition experiments with excess host and guest showed that 3 is likely to diffuse in and out of the membrane, while 4 forms an inclusion complex with β-CDV leading to close contact and efficient quenching. Our findings confirm that this dynamic supramolecular system is a versatile model to investigate quenching and recognition processes in bilayer membranes.

Graphical abstract: Fluorescence quenching in β-cyclodextrin vesicles: membrane confinement and host–guest interactions

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Publication details

The article was received on 04 Jun 2015, accepted on 23 Dec 2015 and first published on 04 Jan 2016


Article type: Paper
DOI: 10.1039/C5PP00226E
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Photochem. Photobiol. Sci., 2016,15, 235-243
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    Fluorescence quenching in β-cyclodextrin vesicles: membrane confinement and host–guest interactions

    F. Schibilla, L. Stegemann, C. A. Strassert, F. Rizzo and B. J. Ravoo, Photochem. Photobiol. Sci., 2016, 15, 235
    DOI: 10.1039/C5PP00226E

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