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

0577178 - ÚFCH JH 2024 RIV GB eng J - Journal Article
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
R&D Projects: GA ČR(CZ) GA18-12150S
Institutional support: RVO:61388955
Keywords : Pentasubstituted phospholes * Synthesis * Electrochemical oxidation and reduction * UV/VIS spectra * Fluorescence * Frontier orbitals * Quantum chemical calculations
OECD category: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis)
Impact factor: 6.6, year: 2022
Method of publishing: Limited access

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.
Permanent Link: https://hdl.handle.net/11104/0346400