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Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations

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    0577178 - ÚFCH JH 2024 RIV GB eng J - Článek v odborném periodiku
    Koláčná, Lucie - Polák, P. - Liška, Alan - Tobrman, T. - Ludvík, Jiří
    Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations.
    Electrochimica acta. Roč. 468, NOV 2023 (2023), č. článku 143073. ISSN 0013-4686. E-ISSN 1873-3859
    Grant CEP: GA ČR(CZ) GA18-12150S
    Institucionální podpora: RVO:61388955
    Klíčová slova: Pentasubstituted phospholes * Synthesis * Electrochemical oxidation and reduction * UV/VIS spectra * Fluorescence * Frontier orbitals * Quantum chemical calculations
    Obor OECD: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
    Impakt faktor: 5.5, rok: 2023
    Způsob publikování: Omezený přístup
    DOI: https://doi.org/10.1016/j.electacta.2023.143073

    lambda 3-1H-Phosphole is a unique heterocyclic compound characterized by low aromaticity with a limited number of cross-coupling reactions to allow side-chain modification. This severely limits the use of pentasubstituted phospholes in materials chemistry, including organic light-emitting diodes (OLEDs), organic solar cells (OSCs) or probes. Therefore, we developed a procedure for simple side-chain modification by Suzuki reactions. The syn-thesized pentasubstituted phospholes with a pi-conjugated arm in position 2 of the phosphole ring were inves-tigated electrochemically. In addition to the electrochemical study, we measured also the UV-VIS and fluorescence spectra for the prepared 1H-phospholes. The experimentally acquired data were correlated with quantum chemical calculations. The oxidation and reduction of all derivatives in acetonitrile at various elec-trodes is (quasi)reversible, the respective potentials as well as the extent of intramolecular electron communi-cation and pi-delocalization depend on the combination of electron withdrawing and donating substituents. The difference between the first oxidation and the first reduction potential (Delta E1) can be correlated with excitation energy.
    Trvalý link: https://hdl.handle.net/11104/0346400

     
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