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Excited state intramolecular proton transfer in 3-hydroxy flavone and 5-hydroxy flavone: A DFT based comparative study

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Abstract

Potential energy (PE) curves for the intramolecular proton transfer in the ground (GSIPT) and excited (ESIPT) states of 3-hydroxy-flavone (3HF) and 5-hydroxy-flavone (5HF) were studied using DFT/B3LYP (6-31G (d,p)) and TD-DFT/B3LYP (6-31G (d,p)) level of theory respectively. Our calculations suggest the non-viability of ground state intramolecular proton transfer for both the compounds. Calculated PE curves of 3HF for the ground and excited singlet states proton transfer process explain its four state laser diagram. Excited states PE calculations support the ESIPT process to both 5HF and 3HF. The difference in ESIPT emission process of 3HF and 5HF have been explained in terms of HOMO and LUMO electron distribution of the enol and keto tautomer of these two compounds.

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Acknowledgments

We gratefully acknowledge the financial support received from Department of Science & Technology (ref. No. SR/FTP/PS-60/2003) and University Grant Commission, New Delhi for carrying out this research work.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Technology, Vidyasagar University, Midnapore, 721 102, W.B, India

    Sankarlal Ash, Sankar Prasad De, Santanu Pyne & Ajay Misra

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  1. Sankarlal Ash
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  2. Sankar Prasad De
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Correspondence to Ajay Misra.

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Ash, S., De, S.P., Pyne, S. et al. Excited state intramolecular proton transfer in 3-hydroxy flavone and 5-hydroxy flavone: A DFT based comparative study. J Mol Model 16, 831–839 (2010). https://doi.org/10.1007/s00894-009-0578-y

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