Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarityстатья
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Аннотация:A series of cross-conjugated dienones was synthesized to study the dependence of physico-
chemical characteristics on the nature of substituents in the aromatic groups of symmetric
cyclopentanone dibenzylidene derivatives. The structure of compounds was established by
electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds
obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone
molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The
low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was
detected using variable-temperature X-ray diffraction and differential scanning calorimetry.
Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry.
Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was
found, that allows us to recommend the use of the data obtained in the correlation analysis of
other compounds of this class.