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Structural, Electronic and Charge Transfer Studies of Highly Sensitive Fluorescent Probe 2-((E)-2-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)vinyl)phenol: Quantum Chemical Investigations

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Abstract

This article presents a facile synthesis of novel class of bluish-green fluorescent 2-((E)-2-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)vinyl)phenol [PPIVP] and their optical, electrochemical and thermal properties. Detailed photophysical and quantum chemical studies have been performed to elucidate the origin of the dual emission shifts. PPIVP undergo excited state intramolecular proton transfer (ESIPT) reaction leading a large Stoke’s shifted fluorescence emission from the phototautomer. The results of quantum chemical investigations not only confirmed the intramolecular charge transfer characteristics of the ESIPT tautomers but also provided a rational for the observed high fluorescence quantum efficiency in the solid state. The high photoluminescence quantum yield in the solid state is ascribed to twisted chromophores due to phenyl substituents at 1,2-position of the phenanthroimidazole ring which restricted intramolecular motion, leading to an optically allowed lowest optical transition without self quenching.

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Acknowledgments

One of the authors Prof. J. Jayabharathi is thankful to DST [No. SR/S1/IC-73/2010], DRDO (NRB-213/MAT/10-11) and CSIR (NO 3732/NS-EMRII) for providing funds to this research study.

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Authors and Affiliations

  1. Department of Chemistry, Annamalai University, Annamalainagar, 608 002, Tamilnadu, India

    V. Thanikachalam, J. Jayabharathi, A. Arunpandiyan & P. Ramanathan

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  1. V. Thanikachalam
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  2. J. Jayabharathi
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Correspondence to V. Thanikachalam.

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Thanikachalam, V., Jayabharathi, J., Arunpandiyan, A. et al. Structural, Electronic and Charge Transfer Studies of Highly Sensitive Fluorescent Probe 2-((E)-2-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)vinyl)phenol: Quantum Chemical Investigations. J Fluoresc 24, 377–387 (2014). https://doi.org/10.1007/s10895-013-1302-y

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