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Spectral investigations on 2,3-bis(chloromethyl)-1,4- anthraquinone: solvent effects and host–guest interactions

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Abstract

Solvent effects on 2,3-bis(chloromethyl)-1,4-anthraquinone (DCMAQ) and the molecular recognition of DCMAQ in calix[8]arene were investigated using optical absorption and fluorescence emission techniques. Optical absorption spectra show n→π* band in 350–500 nm region. It also indicates that the dipole–dipole interaction and solvent reorganization energies are responsible for the observed features in different solvents. The observed quantum yield of DCMAQ in different solvents is due to the formation of intermolecular hydrogen bond and reorientation of solvent molecule in the excited state of DCMAQ. Excited state dipole moment of DCMAQ is calculated by solvatochromic data and it shows a higher excited state dipole moment than ground state dipole moment. Optical absorption and fluorescence studies of DCMAQ in calix[8]arene elucidate the evidence for the formation of complex between DCMAQ and calix[8]arene. The inclusion ratios and inclusion constant of the host–guest complexes are also determined.

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Acknowledgements

The one of these authors (MU) is thankful to DST, Government of India for financial assistance under Women Scientist Scheme. 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. UGC, Government of India is also acknowledged for financial assistance to procure a UV-160 Shimadzu Spectrophotometer in the School of Chemistry, Madurai Kamaraj University.

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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 Organic Chemistry, UMR CNRS 6517, University of Méditerranée, Faculty of Pharmacy, 27 Bd Jean Moulin, 13385, Marseille Cedex 5, France

    P. Vanelle & T. Terme

  3. 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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Umadevi, M., Vanelle, P., Terme, T. et al. Spectral investigations on 2,3-bis(chloromethyl)-1,4- anthraquinone: solvent effects and host–guest interactions. J Fluoresc 16, 569–579 (2006). https://doi.org/10.1007/s10895-006-0093-9

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