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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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Article information


Submitted
11 Sep 2017
Accepted
22 Sep 2017
First published
22 Sep 2017

Org. Biomol. Chem., 2017,15, 8544-8552
Article type
Paper

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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