Synthesis and Photoswitching Studies of Difurylperfluorocyclopentens with Extended π-Systems

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Chemistry - A European Journal. 2011, 17(24), pp. 6663-6672. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201003716
Zusammenfassung

In an attempt to design molecular optoelectronic switches functioning in molecular junctions between two metal tips, we synthesized a set of photochromic compounds by extending the p-system of 1,2-bis-(2-methyl-5-formylfuran- 3-yl)perfluorocyclopentene through suitable coupling reactions involving the formyl functions, thereby also introducing terminal groups with a binding capacity to gold. Avoiding the presence of gold-binding sulphur atoms in the photoreactive centre, as they are present in the frequently used analogous thienyl compounds, the newly synthesized compounds should be more suitable for the purpose indicated. The kinetics of reversible photoswitching of the new compounds by UV and visible light was quantitatively investigated in solution. The role of conformational flexibility of the p-system for the width of the UV/Vis spectra was clarified by using quantum chemical calculations with time-dependent (TD)-DFT. As a preliminary test of the potential of the new compounds to serve as optoelectronic molecular switches, monolayer formation and photochemical switching on gold surfaces was observed by using surface plasmon resonance.

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530 Physik
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electrocyclic reactions, photoswitches, molecular electronics, photochromism, surface plasmon resonance
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ISO 690SYSOIEV, Dmytro, Artem FEDOSEEV, Youngsang KIM, Thomas E. EXNER, Johannes BONEBERG, Thomas HUHN, Paul LEIDERER, Elke SCHEER, Ulrich GROTH, Ulrich STEINER, 2011. Synthesis and Photoswitching Studies of Difurylperfluorocyclopentens with Extended π-Systems. In: Chemistry - A European Journal. 2011, 17(24), pp. 6663-6672. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201003716
BibTex
@article{Sysoiev2011-06-06Synth-14006,
  year={2011},
  doi={10.1002/chem.201003716},
  title={Synthesis and Photoswitching Studies of Difurylperfluorocyclopentens with Extended π-Systems},
  number={24},
  volume={17},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={6663--6672},
  author={Sysoiev, Dmytro and Fedoseev, Artem and Kim, Youngsang and Exner, Thomas E. and Boneberg, Johannes and Huhn, Thomas and Leiderer, Paul and Scheer, Elke and Groth, Ulrich and Steiner, Ulrich}
}
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