Effect of substituents on spectral, luminescent and time-resolved characteristics of 2,5-diarylidene derivatives of cyclopentanone

Abstract

Spectral, luminescent and time-resolved characteristics of 2,5-dibenzylidenecyclopentanone and its symmetrical derivatives (bis(N,N-diethylamino-), dimethoxy-, tetramethoxy-, dimethylthio-, and bis-18- crown-6 derivative) have been studied in media of different polarity (cyclohexane, toluene, acetonitrile, DMSO, and methanol) at room temperature. The absorption maximum of dibenzylidenecyclopentanone shifts bathochromically by 15 nm with an increase in polarity of the medium (cyclohexane–methanol). The introduction of electron-donating substituents in the aromatic rings of dibenzylidenecyclopentanone also results in a bathochromic shift of the absorption maximum by 100–130 nm in the media of different polarity and shifts the fluorescence maximum by 130 nm relative to the maximum of the dimethoxy derivative. Upon laser irradiation of oxygen-free solutions of dibenzylidenecyclopentanone and its tetramethoxy- and bis-18-crown-6 derivatives in acetonitrile, the triplet state with a half-life time of 0.3–1 μs is generated. For dimethoxy-, dimethylthio-, tetramethoxy-, and bis-18-crown-6 derivatives of dibenzylidenecyclopentanone, the isomers with a lifetime of ~50 ms are formed.