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Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations
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SYSNO ASEP 0577178 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Pentasubstituted Phospholes with extended π-conjugated Arm Synthesis, electrochemistry, spectra and quantum chemical calculations Author(s) Koláčná, Lucie (UFCH-W) ORCID, RID, SAI
Polák, P. (CZ)
Liška, Alan (UFCH-W) RID, ORCID
Tobrman, T. (CZ)
Ludvík, Jiří (UFCH-W) RID, ORCIDArticle number 143073 Source Title Electrochimica acta. - : Elsevier - ISSN 0013-4686
Roč. 468, NOV 2023 (2023)Number of pages 9 s. Language eng - English Country GB - United Kingdom Keywords Pentasubstituted phospholes ; Synthesis ; Electrochemical oxidation and reduction ; UV/VIS spectra ; Fluorescence ; Frontier orbitals ; Quantum chemical calculations Subject RIV CG - Electrochemistry OECD category Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis) R&D Projects GA18-12150S GA ČR - Czech Science Foundation (CSF) Method of publishing Limited access Institutional support UFCH-W - RVO:61388955 UT WOS 001080793400001 EID SCOPUS 85170424902 DOI https://doi.org/10.1016/j.electacta.2023.143073 Annotation 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. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2024 Electronic address https://hdl.handle.net/11104/0346400
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