Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
| Autor: | Sven Rau, Kamil Witas, Alexander K. Mengele, Djawed Nauroozi, Stephan Kupfer, Nicolas Meitinger |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Quantum chemical simulations
Solvatochromie DDC 540 / Chemistry & allied sciences Elektrochemie Organic Chemistry Solvatochromism Cyclopentadienonderivate Electrochemistry Photochemistry Aryls chemistry.chemical_compound Cyclopentadienone chemistry ddc:540 Physical and Theoretical Chemistry Quantum chemistry |
| Zdroj: | European Journal of Organic Chemistry. 2020:6555-6562 |
| ISSN: | 1099-0690 1434-193X |
| Popis: | Substitution at tetraaryl cyclopentadienones is known to affect the photophysical properties of the molecules. In a joint experimental and theoretical investigation, a series of differently substituted tetraaryl cyclopentadienones are studied upon so far unprecedented negative solvatochromic effect and, the impact of substituents on the electrochemical behavior. The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C���H������O and C���H�������� interactions in the solid state. publishedVersion |
| Databáze: | OpenAIRE |
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