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A Theoretical Study of the UV/Visible Absorption and Emission Solvatochromic Properties of Solvent-Sensitive Dyes

Authors

  • Wen-Ge Han Dr.,

    1. Department of Molecular Biology, TPC-15, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA, Fax: (+1) 858-784-8896
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  • Tiqing Liu Dr.,

    1. Department of Molecular Biology, TPC-15, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA, Fax: (+1) 858-784-8896
    2. Current address: Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA
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  • Fahmi Himo Dr.,

    1. Department of Molecular Biology, TPC-15, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA, Fax: (+1) 858-784-8896
    2. Current address: Royal Institute of Technology, SCFAB, Department of Biotechnology, Theoretical Chemistry, 106 91 Stockholm, Sweden
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  • Alexei Toutchkine Dr.,

    1. Department of Cell Biology, CB 164, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
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  • Donald Bashford Prof.,

    1. Department of Molecular Biology, TPC-15, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA, Fax: (+1) 858-784-8896
    2. Current address: Hartwell Center, St. Jude Children's Research Hospital, 332 N. Lauderdale St., Memphis TN 38105, USA
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  • Klaus M. Hahn Prof.,

    1. Department of Cell Biology, CB 164, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA
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  • Louis Noodleman Prof.

    1. Department of Molecular Biology, TPC-15, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA, Fax: (+1) 858-784-8896
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Abstract

Using the density-functional vertical self-consistent reaction field (VSCRF) solvation model, incorporated with the conductor-like screening model (COSMO) and the self-consistent reaction field (SCRF) methods, we have studied the solvatochromic shifts of both the absorption and emission bands of four solvent-sensitive dyes in different solutions. The dye molecules studied here are: S-TBA merocyanine, Abdel-Halim's merocyanine, the rigidified aminocoumarin C153, and Nile red. These dyes were selected because they exemplify different structural features likely to impact the solvent-sensitive fluorescence of “push-pull”, or merocyanine, fluorophores. All trends of the blue or red shifts were correctly predicted, comparing with the experimental observations. Explicit H-bonding interactions were also considered in several protic solutions like H2O, methanol and ethanol, showing that including explicit H-bonding solvent molecule(s) in the calculations is important to obtain the correct order of the excitation and emission energies. The geometries, electronic structures, dipole moments, and intra- and intermolecular charge transfers of the dyes in different solvents are also discussed.

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