Properties of Radical Cations Generated by the Pulse Radiolysis of 1,ω-Bis(diarylethenyl)alkanes. Trapping of Distonic 1,4-Radical Cation by Molecular Dioxygen

Physical and chemical properties of radical cations generated from Ar2C=CH(CH2)nCH=CAr2 (Ar = 4-CH3OC6H4, n = 2–4) were studied by use of pulse radiolysis and γ-radiolysis techniques. When n = 3 and 4, 1,4-radical cations were formed via intramolecular cyclization of initially formed radical cations. The 1,4-radical cations were trapped by molecular dioxygen at the diarylalkylmethyl radical site, which suggests the “distonic” character of the species.

[1]  T. Tamai,et al.  Photooxygenation of 1, ω-bis(diarylethenyl)alkanes via photoinduced electron transfer: Formation of bicyclic peroxides , 1993 .

[2]  S. Tojo,et al.  Acyclic 1,4-radical cations. Direct observation and stability , 1991 .

[3]  S. Steenken,et al.  Nanosecond laser flash photolytic generation and lifetimes in solvolytic media of diarylmethyl and p-methoxyphenethyl cations , 1988 .

[4]  S. Hammerum.  Distonic radical cations in gaseous and condensed phase , 1988 .

[5]  S. Mattes,et al.  Photochemical electron-transfer reactions of 1,1-diarylethylenes , 1986 .

[6]  W. Bouma,et al.  Detection of the prototype phosphonium (CH2PH3), sulfonium (CH2SH2), and chloronium (CH2ClH) ylides by neutralization-reionization mass spectrometry: a theoretical prediction , 1984 .

[7]  E. Haselbach,et al.  Organic radical ions in rigid systems , 1984 .

[8]  K. Gollnick,et al.  Formation of a 1,2-dioxane by electron-transfer photooxygenation of 1,1-di(p-anisyl)ethylene , 1984 .

[9]  O. Brede,et al.  Primary processes of the radiation-induced cationic polymerization of aromatic olefins studied by pulse radiolysis , 1982 .

[10]  T. Majima,et al.  Redox-photosensitized reactions. 7. Aromatic hydrocarbon-photosensitized electron-transfer reactions of furan, methylated furans, 1,1-diphenylethylene, and indene with p-dicyanobenzene , 1981 .

[11]  R. Haynes,et al.  Direct formation of 3,3,6,6-Tetraaryl-1,2-dioxans from 1,1-Diarylethylenes and oxygen, catalysed by antimony(V) chloride , 1978 .

[12]  D. Arnold,et al.  Radical ions in photochemistry. I. 1,1-Diphenylethylene cation radical , 1973 .

[13]  T. Shida,et al.  Molecular Ions in Radiation Chemistry. III. Absorption Spectra of Aromatic-Hydrocarbon Cations and Anions in Organic Glasses , 1966 .