Addition of aryl and fluoroalkyl radicals to fullerene C{sub 70}: ESR detection of five regioisomeric adducts and density functional calculations

Journal Article · Wed Aug 14 04:00:00 EDT 1996 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja960979h· OSTI ID:381797

Borghi, R; Lunazzi, L; Placucci, G ^[1]; Krusic, P J; Dixon, D A ^[2]; Matsuzawa, Nobuyuki; Ata, Masafumi ^[3]

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1. Univ. of Bologna (Italy)
2. E.I. du Pont de Nemours & Co., Wilmington, DE (United States)
3. Sony Research Center, Yokahoma (Japan)

The addition of several photochemically generated aryl and fluoroalkyl radicals to fullerene C{sub 70} was studied by electron spin resonance and the results were compared with those obtained with C{sub 60}. While simple alkyl radicals afford only three of the five expected RC{sub 70}{sup .} regioisomers, the more reactive aryl and fluoroalkyl radicals give rise to four, except for the trifluoromethyl radical which yielded for the first time the ESR spectra of all five expected isomers. Semiempirical MO calculations and density functional theory calculations were carried out for HC{sub 60}{sup .} and for the five HC{sub 70}{sup .} regioisomers as models for the corresponding alkyl, aryl, and fluoroalkyl analogs in order to describe the unpaired electron distribution in these radical species and as an aid in the assignment of the observed spectra to specific RC{sub 70}{sup .} regioisomers. 49 refs., 7 figs., 6 tabs.

• OSTI ID: 381797
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 32 Vol. 118; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
40 CHEMISTRY
66 PHYSICS
99 GENERAL AND MISCELLANEOUS
ADDUCTS
ALKYL RADICALS
ARYL RADICALS
CALCULATION METHODS
CHEMICAL REACTIONS
ELECTRON SPIN RESONANCE
FULLERENES
ISOMERS
MOLECULAR MODELS
MOLECULAR ORBITAL METHOD
ORGANIC FLUORINE COMPOUNDS