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Issue 40, 2017
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ESIPT-induced fluorescent o-hydroxycinnamate: a self-monitoring phototrigger for prompt image-guided uncaging of alcohols

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Abstract

o-Hydroxycinnamate derivatives are well-known phototriggers for fast and direct release of alcohols and amines without proceeding through the cleavage of carbonate or carbamate linkages. Despite these unique features, o-hydroxycinnamates lack extensive applications in biological systems mainly because of their non-fluorescent nature. To overcome this limitation, we have attached a 2-(2′-hydroxyphenyl) benzothiazole (HBT) moiety, capable of rapid excited-state intramolecular proton transfer (ESIPT) to the o-hydroxycinnamate group. The ESIPT effect induced two major advantages to the o-hydroxycinnamate group: (i) large Stokes’ shifted fluorescence (orange colour) properties and (ii) distinct fluorescence colour change upon photorelease. In vitro studies exhibited an image guided, photoregulated release of bioactive molecules by the o-hydroxycinnamate–benzothiazole–methyl salicylate conjugate and real-time monitoring of the release action.

Graphical abstract: ESIPT-induced fluorescent o-hydroxycinnamate: a self-monitoring phototrigger for prompt image-guided uncaging of alcohols

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Publication details

The article was received on 11 Sep 2017, accepted on 22 Sep 2017 and first published on 22 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02280H
Citation: Org. Biomol. Chem., 2017,15, 8544-8552
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    ESIPT-induced fluorescent o-hydroxycinnamate: a self-monitoring phototrigger for prompt image-guided uncaging of alcohols

    A. Paul, R. Mengji, O. A. Chandy, S. Nandi, M. Bera, A. Jana, A. Anoop and N. D. P. Singh, Org. Biomol. Chem., 2017, 15, 8544
    DOI: 10.1039/C7OB02280H

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