Issue 41, 2016

Near-infrared fluorescence of π-conjugation extended benzothiazole and its application for biothiol imaging in living cells

Abstract

Two new π-conjugation extended benzothiazole derivatives bearing single (2) or double (3) vinyl groups between benzothiazolyl and 4-methylphenol moieties in 2,6-dibenzothiazolyl-4-methylphenol (1) have been synthesized and their photophysical properties were studied. In nonpolar solvents, 2 showed a keto tautomer emission from the excited state intramolecular proton transfer (ESIPT) at 626 nm, remarkably red-shifted compared to the keto tautomer fluorescence of 1 (568 nm), whereas 3 only exhibited an enol emission at 420 nm. However, a near-infrared (NIR) emission at 616/688 nm for 2/3 from the deprotonated anionic species was observed in polar solvents, which is farther red-shifted compared to that for deprotonated 1 (516 nm). With the aid of computational studies, the experimental observations were rationalized according to the efficient extension of π-conjugation of the molecular backbones in 2 and 3. Furthermore, a white emission with a broad band between 400 and 800 nm from 3 was also observed in a polar–nonpolar solvent mixture, where nearly pure white coordinates (0.33, 0.35) from the CIE chromaticity diagram were successfully achieved. By masking the phenol group in 3, a NIR fluorescent probe (4) for biothiols was constructed, which allows for imaging applications in living cells.

Graphical abstract: Near-infrared fluorescence of π-conjugation extended benzothiazole and its application for biothiol imaging in living cells

Supplementary files

Article information

Article type
Paper
Submitted
14 Jun 2016
Accepted
19 Sep 2016
First published
19 Sep 2016

J. Mater. Chem. B, 2016,4, 6662-6669

Near-infrared fluorescence of π-conjugation extended benzothiazole and its application for biothiol imaging in living cells

X. Zhang, J. Liu, W. Ma and M. Yang, J. Mater. Chem. B, 2016, 4, 6662 DOI: 10.1039/C6TB01465H

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