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Issue 21, 2018
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Tuning the emission of a water-soluble 3-hydroxyflavone derivative by host–guest complexation

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Abstract

3-Hydroxyflavone derivatives have great potential as fluorescent probes for bio-labeling in aqueous medium. They were extensively studied in various organic solvents for the “excited state intramolecular proton transfer” process, but seldom addressed in aqueous solution due to the poor water solubility. Herein, an amphiphilic molecule bearing 3-hydroxyflavone and oligo(ethylene oxide) (denoted as 3HF-EO) was designed and synthesized. Different from the fluorescence in organic solvents, 3HF-EO in aqueous solution showed a remarkable single fluorescence emission, which is ascribed to the fluorescence of its anionic species. We found that the fluorescence intensity could be efficiently tuned via host–guest complexation. α-CD has little effect on the emission, while β-CD and γ-CD lead to enhanced and reduced emissions of 3HF-EO, respectively. The 1H NMR and 2D NOESY NMR spectra indicate that α-CD barely had any interaction with 3HF-EO, while β-CD and γ-CD formed complexes with one and two 3HF-EO molecules, respectively. These results provide a sound explanation for the modulated fluorescence intensity.

Graphical abstract: Tuning the emission of a water-soluble 3-hydroxyflavone derivative by host–guest complexation

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Publication details

The article was received on 20 Feb 2018, accepted on 17 Mar 2018 and first published on 20 Mar 2018


Article type: Paper
DOI: 10.1039/C8SM00349A
Citation: Soft Matter, 2018,14, 4231-4237
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    Tuning the emission of a water-soluble 3-hydroxyflavone derivative by host–guest complexation

    D. Li, Y. Xing, L. Ding, C. Wu, G. Hou and B. Song, Soft Matter, 2018, 14, 4231
    DOI: 10.1039/C8SM00349A

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