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Dendralene-type TTF vinylogs containing a 1,3-diselenole ring.

R R Amaresh1, D Liu, T Konovalova

  • 1Chemistry Department, University of Alabama, P.O. Box 870336, Tuscaloosa, AL 35487-0336, USA.

The Journal of Organic Chemistry
|November 10, 2001
PubMed
Summary

Researchers synthesized novel dendralene-type vinylogs of tetrathiafulvalene (TTF) incorporating a 1,3-diselenole unit. Their electrochemical properties and radical cation behavior were investigated using EPR spectroscopy and calculations.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Tetrathiafulvalene (TTF) derivatives are crucial in organic electronics.
  • Dendralene structures offer unique electronic and physical properties.
  • Incorporating selenium into organic molecules can tune their electronic characteristics.

Purpose of the Study:

  • To synthesize novel TTF vinylogs featuring a 1,3-diselenole moiety.
  • To investigate the electrochemical behavior of these novel dendrimers.
  • To study the electronic structure of their radical cations using EPR.

Main Methods:

  • Synthesis of 2-diformylmethylene-1,3-diselenole.
  • Condensation reactions with dithiolium phosphonium bromides and phosphonates.

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  • Electrochemical studies (cyclic voltammetry, etc.).
  • Electron Paramagnetic Resonance (EPR) spectroscopy.
  • Computational calculations on radical cations.

    • Main Results:

    • Successful synthesis of dendralene-type TTF vinylogs with a 1,3-diselenole unit.
    • Characterization of their electrochemical properties.
    • EPR measurements provided insights into the radical cation states.
    • Calculations correlated well with experimental EPR data.

    Conclusions:

    • The synthesized compounds represent a new class of TTF-based dendrimers.
    • The 1,3-diselenole moiety influences the electronic properties.
    • EPR and computational studies elucidated the electronic structure of radical cations.