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Two-photon absorbing 8-hydroxy-benzo[g]coumarins with giant Stokes shifts: An environment-insensitive dye platform for probing biomolecules

Abstract

Fluorescent compounds with distinct photophysical properties are essential in the development of optical probes for chemical, biological, and environmental species, in addition to optoelectronic devices. In that context we synthesized a series of 3-substituted-8-hydroxybenzo[g]coumarin derivatives and characterized their photophysical and cellular imaging properties. Being dipolar π-extended coumarin analogues, they have intramolecular charge-transfer character and good two-photon imaging capability as shown for two selected dyes. Most of the dyes emit in a wavelength range of 530–580 nm in aqueous media and show large Stokes shifts as high as 197 nm. Inspite of its dipolar nature, 3-pyridinium-substituted derivative 5h notably shows insignificant solvatochromism as well as viscosity- and polarity-insensitive emission intensity, offering an ideal dye platform for probing biological targets. As a demonstration, we prepared an esterase probe based on it, which shows ratiometric sensing behavior.

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Publication details

The article was received on 01 May 2018, accepted on 13 Jun 2018 and first published on 13 Jun 2018


Article type: Paper
DOI: 10.1039/C8TB01144C
Citation: J. Mater. Chem. B, 2018, Accepted Manuscript
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    Two-photon absorbing 8-hydroxy-benzo[g]coumarins with giant Stokes shifts: An environment-insensitive dye platform for probing biomolecules

    S. Sarkar, M. Santra, S. Singha, Y. W. Jun, Y. J. Reo, H. R. Kim and K. H. Ahn, J. Mater. Chem. B, 2018, Accepted Manuscript , DOI: 10.1039/C8TB01144C

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