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Photophysical Properties of Trans-2-[4-(dimethylamino)styryl]-3-ethyl-1,3-benzothiazolium Perchlorate, a New Structural Analog of Thioflavin T

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Journal of Applied Spectroscopy Aims and scope

Spectral properties of a newly synthesized thiofl avin T (ThT) derivative, trans-2-[4-(dimethylamino)styryl]-3-ethyl-1,3-benzothiazolium perchlorate (DMASEBT) with absorption and fluorescence spectra shifted to longer wavelengths (than ThT), were studied. Quantum-chemical calculations established that DMASEBT is planar in the ground state. The energy minimum of the excited molecule corresponded to a twisted conformation (TICT-state) with a 90° angle between the planar fragments. Charge in the molecule redistributed and a non-fluorescing TICT-state was formed if the fragments rotated. Fluorescence occurred from the non-equilibrium excited state (LE-state). It was shown that limited torsional rotation of the molecular fragments and; therefore, a decreased probability of transitioning into the non-fluorescing TICT-state, were responsible for the significantly increased quantum yield and fluorescence lifetime of DMASEBT upon increasing the solvent viscosity and incorporating it into amyloid fibrils.

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Authors and Affiliations

  1. Yanka Kupala State University, 22 Ozheshko Str., Grodno, 230023, Belarus

    A. V. Lavysh & A. A. Maskevich

  2. Institute of Cytology, Russian Academy of Sciences, St. Petersburg, Russia

    A. I. Sulatskaya, I. M. Kuznetsova & K. K. Turoverov

  3. Belarusian State University, Minsk, Belarus

    A. A. Lugovskii & E. S. Voropay

  4. St. Petersburg State Polytechnical University, St. Petersburg, Russia

    I. M. Kuznetsova & K. K. Turoverov

Authors
  1. A. V. Lavysh
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  2. A. I. Sulatskaya
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  3. A. A. Lugovskii
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  4. E. S. Voropay
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  5. I. M. Kuznetsova
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  6. K. K. Turoverov
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  7. A. A. Maskevich
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Correspondence to A. V. Lavysh.

Additional information

Translated from Zhurnal Prikladnoi Spektroskopii, Vol. 81, No. 2, pp. 209–218, March–April, 2014.

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Lavysh, A.V., Sulatskaya, A.I., Lugovskii, A.A. et al. Photophysical Properties of Trans-2-[4-(dimethylamino)styryl]-3-ethyl-1,3-benzothiazolium Perchlorate, a New Structural Analog of Thioflavin T . J Appl Spectrosc 81, 205–213 (2014). https://doi.org/10.1007/s10812-014-9911-z

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  • DOI: https://doi.org/10.1007/s10812-014-9911-z

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