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Comprehensive DFT and TD-DFT Studies on the Photophysical Properties of 5,6-Dichloro-1,3-Bis(2-Pyridylimino)-4,7-Dihydroxyisoindole: A New Class of ESIPT Fluorophore

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Abstract

Hanson et al. [Org. Lett., 2011] reported the absorption and emission spectrum of 5,6-dichloro-1,3-bis(2-pyridylimino)-4,7-dihydroxyisoindole but the excited-state intramolecular proton transfer (ESIPT) process was not investigated. The photo-physical behaviour of 5,6-dichloro-1,3-bis(2-pyridylimino)-4,7-dihydroxyisoindole was studied using the density functional theory (DFT) and time-dependent density functional theory (TD-DFT). The functional used was B3LYP and 6-31G(d) was the basis set for all the atoms. All the ten tautomers were studied for the absorption and emission properties. It is found that the tautomer where hydroxyl groups are syn to nitrogen of isoindoline ring is most stable and thus, responsible for the ESIPT process. The computed absorption and emission values of tautomers using TD-DFT are in good agreement with those obtained experimentally.

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Acknowledgments

SK is thankful to UGC for giving study leave (FIP) and SIES college for sanctioning the study leave. PR and LR acknowledge facilities from the University of Mauritius.

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Authors and Affiliations

  1. Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, MH, 400019, India

    Santosh Kataria & Nagaiyan Sekar

  2. Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit, 80837, Mauritius

    Lydia Rhyman & Ponnadurai Ramasami

  3. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box. 2457, Riyadh, 11451, Kingdom of Saudi Arabia

    Ponnadurai Ramasami

  4. Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria, 0003, South Africa

    Ponnadurai Ramasami

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  1. Santosh Kataria
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  2. Lydia Rhyman
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  3. Ponnadurai Ramasami
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  4. Nagaiyan Sekar
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Correspondence to Ponnadurai Ramasami or Nagaiyan Sekar.

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Kataria, S., Rhyman, L., Ramasami, P. et al. Comprehensive DFT and TD-DFT Studies on the Photophysical Properties of 5,6-Dichloro-1,3-Bis(2-Pyridylimino)-4,7-Dihydroxyisoindole: A New Class of ESIPT Fluorophore. J Fluoresc 26, 1805–1812 (2016). https://doi.org/10.1007/s10895-016-1872-6

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