13698-26-5Relevant academic research and scientific papers
Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
Meitinger, Nicolas,Mengele, Alexander K.,Witas, Kamil,Kupfer, Stephan,Rau, Sven,Nauroozi, Djawed
, p. 6555 - 6562 (2020)
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···π interactions in the solid state.
