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3-Pyrrolyl BODIPY Based Selective Cu2+ Ion “Off-On” Fluorescent Sensor

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Abstract

3-Pyrrolyl BODIPY-Schiff base conjugate was synthesized by treating α-formyl 3-pyrrolyl BODIPY with o-hydroxy aniline in ethanol at reflux followed by recrystallization. The conjugate was thoroughly characterized by HR-MS, 1D & 2D NMR and X-ray crystallography. The X-ray analysis revealed that the BODIPY core was in planar arrangement, with the central boron atom coordinated with two pyrrole nitrogens of dipyrrin moieties and two axial fluoride ions in a tetrahedral geometry. The 3-pyrrolyl BODIPY-Schiff base conjugate exhibited a strong absorption band at 616 nm and broad weak fluorescence band at 660 nm. The absorption and fluorescence titration studies with various metal ions revealed that 3-pyrrolyl BODIPY can act as colorimetric optical sensor and specific “off-on” fluorescent sensor for Cu2+ ion.

Graphical abstract

SYNOPSIS: 3-Pyrrolyl BODIPY-Schiff base conjugate was synthesized starting from α-formyl 3-pyrrolyl BODIPY. The conjugate was thoroughly characterized by HR-MS, NMR and X-ray crystallography. The absorption and fluorescence titration studies with various metal ions revealed that 3-pyrrolyl BODIPY can act as specific “off-on” fluorescent sensor for Cu2+ ion.

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Authors and Affiliations

  1. Department of Chemistry, IIT Bombay, Powai, Mumbai, India

    Panchavarnam Sabari & Mangalampalli Ravikanth

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  1. Panchavarnam Sabari
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  2. Mangalampalli Ravikanth
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Correspondence to Mangalampalli Ravikanth.

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Special Issue on Beyond Classical Chemistry

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Sabari, P., Ravikanth, M. 3-Pyrrolyl BODIPY Based Selective Cu2+ Ion “Off-On” Fluorescent Sensor. J Chem Sci 133, 59 (2021). https://doi.org/10.1007/s12039-021-01922-5

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  • DOI: https://doi.org/10.1007/s12039-021-01922-5

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