Journal
DYES AND PIGMENTS
Volume 120, Issue -, Pages 213-219Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2015.04.016
Keywords
Rhodol; Excited-state intramolecular proton transfer; Sulfite; Benzothiazole; Ratiometric; Fluorescent probe
Funding
- National Natural Science Foundation of China [21475105, 21275117, 21375105]
- Science & Technology Department [2012JM2004]
- Education Department of Shaanxi Province of China [12JK0518]
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2-(2'-Hydroxyphenyl) benzothiazoles (HBT) are well-known excited-state intramolecular proton transfer (ESIPT) molecules and have been ingeniously elaborated for fluorescent probes construction. However, most of HBT-based ratiometric fluorescent probes are based on the phenolic hydroxyl (-OH) protection/deprotection strategy. In this work, we integrate the pi-conjugation interruption reaction and the quinone phenol transduction-activated ESIPT within a benzothiazole-containing rhodol derivative (1), and develop a ratiometric fluorescent probe for sulfite. Upon treating with sulfite, the pi-conjugation system of 1 was interrupted and the quinone phenol transduction occurred simultaneously, which leads to the ESIPT process between the phenolic OH and benzothiazole unit upon photoexcitation. The above conversions result in the decrease of the emission band at 578 nm along with a concomitant increase of a new fluorescence peak at 453 nm. The fluorescent intensity (I-453/I-578) increases linearly with sulfite concentration up to 8 mu M with a detection of 0.22 mu M (38). The proposed probe shows excellent selectivity toward sulfite over other common anions and nucleophiles. Moreover, the cellular imaging experiment indicated probe 1 possesses low cytotoxicity and desirable cell permeability for biological applications. (C) 2015 Elsevier Ltd. All rights reserved.
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