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Spectral Investigations of Solvatochromism and Preferential Solvation on 1,4-Dihydroxy-2,3-Dimethyl-9,10-Anthraquinone

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Abstract

Solvatochromic and preferential solvation of 1,4-dihydroxy-2,3-dimethyl-9,10-anthraquinone (DHDMAQ) have been investigated using optical absorption and fluorescence emission techniques. Optical absorption spectra of DHDMAQ in different solvents show the intra molecular charge transfer band in the region 400–550nm. The observed blue shift with solvent polarity indicates the delocalisation of the excited state, owing to reduction in quasiaromaticity of the chelate rings formed by intra molecular hydrogen bonds, due to electrostatic or hydrogen bonding interaction. This is also confirmed by the observed low oscillator strength and the transition dipole moment. The observed quantum yield of DHDMAQ in different solvents is due to the inter molecular hydrogen bond in the excited state in addition to the intra molecular hydrogen bond. It also reveals from the low oscillator strength, which indicates that the radiative decay is low. Excited state dipole moment of DHDMAQ is calculated by solvatochromic data and it shows a lower value than ground state dipole moment. The preferential solvation parameter shows that in dimethyl formamide (DMF) + ethanol mixture, the DHDMAQ is preferentially solvated by ethanol in DMF rich region and by DMF in ethanol rich region. In the case of DMF + dichloromethane mixture DHDMAQ is preferentially solvated by DMF.

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Acknowledgements

The one of the authors (MU) is thankful to DST, Government of India for financial assistance under Women Scientist Scheme. The One of the authors (BJR) is thankful to DST, Government of India for financial assistance. The author (VR) is thankful to DST, Government of India for grants received to establish the laser laboratory. UGC, Government of India is acknowledged for recognizing laser spectroscopy group activities as among the thrust area of research under DRS and COSIST programs.

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Authors and Affiliations

  1. Department of Physics, Mother Teresa Women’s University, Kodaikanal–624 102, Tamil Nadu, India

    M. Umadevi

  2. Department of Radical Pharmaco-Chemistry, UMR CNRS 6264, Faculty of Pharmacy, University of Méditerranée, 27 Bd Jean Moulin, 13385, Marseille Cedex 5, France

    P. Vanelle & T. Terme

  3. Department of Physics, Lady Doak College, Madurai, India

    Beulah J.M. Rajkumar

  4. Department of Laser Studies, School of Physics, Madurai Kamaraj University, Madurai, 625 021, India

    V. Ramakrishnan

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  1. M. Umadevi
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  2. P. Vanelle
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  3. T. Terme
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  4. Beulah J.M. Rajkumar
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  5. V. Ramakrishnan
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Correspondence to M. Umadevi.

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Umadevi, M., Vanelle, P., Terme, T. et al. Spectral Investigations of Solvatochromism and Preferential Solvation on 1,4-Dihydroxy-2,3-Dimethyl-9,10-Anthraquinone. J Fluoresc 18, 1139–1149 (2008). https://doi.org/10.1007/s10895-008-0364-8

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  • DOI: https://doi.org/10.1007/s10895-008-0364-8

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