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Electrooptical Absorption Measurements (EOAM) Testify Existence of two Conformers of Prodan and Laurdan with Different Dipole Moments in Equilibrium Ground and Franck-Condon Excited State

Journal of Fluorescence volume 26, pages 1563–1572 (2016)Cite this article

Abstract

The results from the electrooptical absorption measurements (EOAM) on the equilibrium ground and excited Franck-Condon state dipole moments of Prodan and Laurdan in 1,4-dioxane are presented. As follows from experiments Prodan and Laurdan in the equilibrium ground and excited Franck-Condon state have two conformers with considerably different dipole moments. The electrical dipole moments and the transition dipole moment, obtained from the short-wavelength region of the absorption spectrum are parallel. The electrical dipole moments measured at the long-wavelength spectral region are parallel to each other but not parallel to the transition dipole moment m a. The angle θ between the transition dipole moment m a and the dipole moment in the equilibrium ground state μ g of the long-wavelength conformer is about 300 for both probes. Obtained results evidence that donor-acceptor pairs of the short-wavelength and long-wavelength conformers are not located on the same axis. Two low-energy conformers of Prodan have been found by density functional theory (DFT) calculations, differing in the orientation of the carbonyl group towards the naphthalene system.

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Abbreviations

Laurdan:

6-decanoyl-2-dimethylamino-naphthalene

Prodan:

6-propionyl-2-dimethylamino-naphthalene

EOAM:

Electrooptical absorption measurements

DFT:

Density functional theory

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Acknowledgments

N.N.A. thanks German Academic Exchange Service (DAAD) for the scholarship.

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Authors and Affiliations

  1. Institute of Organic Chemistry, J. Gutenberg-University of Mainz, Duesbergweg 10-14, 55099, Mainz, Germany

    N. A. Nemkovich, H. Detert & N. Roeder

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  1. N. A. Nemkovich
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  2. H. Detert
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  3. N. Roeder
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Nemkovich, N.A., Detert, H. & Roeder, N. Electrooptical Absorption Measurements (EOAM) Testify Existence of two Conformers of Prodan and Laurdan with Different Dipole Moments in Equilibrium Ground and Franck-Condon Excited State. J Fluoresc 26, 1563–1572 (2016). https://doi.org/10.1007/s10895-016-1809-0

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Keywords

  • Prodan
  • Laurdan
  • Dipole moments
  • Electrooptical absorption measurements (EOAM)
  • Molecular Stark-effect spectroscopy
  • Conformers