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Photocontrollable Modulation of Frontier Molecular Orbital Energy Levels of Cyclopentenone-Based Diarylethenes

  • Andrey G. Lvov*
    Andrey G. Lvov
    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russian Federation
    Irkutsk National Research Technical University, 83, Lermontov Street, Irkutsk 664074, Russian Federation
    *Email: [email protected]
  • Martin Herder
    Martin Herder
    Department of Chemistry and IRIS Adlershof, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
  • Lutz Grubert
    Lutz Grubert
    Department of Chemistry and IRIS Adlershof, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
    More by Lutz Grubert
  • Stefan Hecht
    Stefan Hecht
    Department of Chemistry and IRIS Adlershof, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
    DWI—Leibniz Institute for Interactive Materials, Forckenbeckstr. 50, 52074 Aachen, Germany
    Institute of Technical and Macromolecular Chemistry, RWTH Aachen University, Worringer Weg 2, 52074 Aachen, Germany
    More by Stefan Hecht
  • , and 
  • Valerii Z. Shirinian
    Valerii Z. Shirinian
    N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp, 119991 Moscow, Russian Federation
Cite this: J. Phys. Chem. A 2021, 125, 17, 3681–3688
Publication Date (Web):April 22, 2021
https://doi.org/10.1021/acs.jpca.1c01836
Copyright © 2021 American Chemical Society

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    Abstract

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    Photoswitchable diarylethenes provide a unique opportunity to optically modulate frontier molecular orbital energy levels, thereby opening an avenue for the design of electronic devices such as photocontrollable organic field-effect transistors (OFETs). In the present work, the absolute position of the frontier orbital levels of nonsymmetrical diarylethenes based on a cyclopentenone bridge has been studied using cyclic voltammetry and density functional theory (DFT) calculations. It has been shown that varying heteroaromatic substituents make it possible to change the absolute positions of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) of both diarylethene photoisomers. The data obtained are used to refine the operation mechanism of the previously developed OFET devices, employing the cyclopentenone-derived diarylethenes at the dielectric/semiconductor interface.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpca.1c01836.

    • Cyclic voltammograms of all compounds and details on quantum chemical calculations (PDF)

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    Cited By

    This article is cited by 3 publications.

    1. Haval A. Hussein, Ghazwan F. Fadhil. Theoretical Investigation of para Amino-Dichloro Chalcone Isomers. Part II: A DFT Structure–Stability Study of the FMO and NLO Properties. ACS Omega 2023, 8 (5) , 4937-4953. https://doi.org/10.1021/acsomega.2c07148
    2. Takashi Tsuno. Organic aspects: photochemistry of alkenes, dienes, polyenes (2020–2021). 2022, 67-124. https://doi.org/10.1039/9781839167676-00067
    3. Edison Salazar, Suzanne Reinink, Shirin Faraji. Providing theoretical insight into the role of symmetry in the photoisomerization mechanism of a non-symmetric dithienylethene photoswitch. Physical Chemistry Chemical Physics 2022, 24 (19) , 11592-11602. https://doi.org/10.1039/D2CP00550F

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