An ESIPT based versatile fluorescent probe for bioimaging live-cells and E. coli under strongly acidic conditions†
a
Manzoor
Ahmad,
a
Sukhvinder
Dhiman,
a
Gulshan
Kumar,
b
Vijay
Luxami,
b
Prabhpreet
Singh
a
and
Subodh
Kumar
*a
Abstract
A 2-(2-hydroxyphenyl)benzothiazole based probe BTNN undergoes a drastic upsurge (∼146-fold, Φ = 69%) in fluorescence intensity (bright green, λem 530 nm) on going from pH 7 to 2. MG-63 cells and E. coli bacteria internalize BTNN without toxicity and its fluorescence intensity is directly correlated to the pH in the cells/bacteria. This response to pH is instantaneous, reversible and stable for over a week. The protonation of the diethylamino nitrogen followed by efficient normal and excited state intramolecular proton transfer (ESIPT) processes of protonated BTNN are responsible for remarkable increase in fluorescence intensity and quantum yield under acidic conditions. Furthermore, polystyrene-BTNN thin films can be used for efficient detection of HCl vapour (2 ppm). This is first example where 2-(2-hydroxyphenyl)benzothiazole derivative can image strong acidic conditions.
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