Competitive intra- and inter-molecular proton transfer in hydroxynaphthyl benzothiazole: selective ratiometric sensing of acetate

doi:10.1016/j.tetlet.2013.05.119

Tetrahedron Letters

Volume 54, Issue 32, 7 August 2013, Pages 4215-4220

https://doi.org/10.1016/j.tetlet.2013.05.119 Get rights and content

Abstract

The receptor, naphthalene based benzothiazole (NHBT) shows acetate selectivity in its absorbance and emission behavior among the various interfering anions. Substantially red shifted absorption band and fluorescence emission of NHBT in pure acetonitrile media were developed which drastically got enhanced upon addition of tetrabutylammonium acetate. Excited-state intermolecular proton transfer in the sensor–anion hydrogen-bonding complex was suggested to be the signaling mechanism. NHBT, a good hydrogen-bonding donor, the ESIPT process is inhibited by the formation of a strong acetate-NHBT intermolecular hydrogen bond complex, and the inhibition mechanism consequently results in ratiometric response in absorption and emission spectroscopy, respectively.

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Acknowledgments

Authors thank the DST and CSIR (Govt. of India) for financial support. A.K.D, K.A. and A.M. acknowledge CSIR for providing fellowships.

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Competitive intra- and inter-molecular proton transfer in hydroxynaphthyl benzothiazole: selective ratiometric sensing of acetate

Abstract

Graphical abstract

Section snippets

Acknowledgments

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