Addition of ketene silyl acetals to the triplet excited state of C{sub 60} via photoinduced electron transfer leading to the fullereneacetates
- Tokyo Inst. of Technology (Japan)
- Osaka Univ. (Japan)
The photochemical carbon-carbon bond formation of C{sub 60} with ketene silyl acetals is described to give a new way for fullerene functionalization chemistry. The photoaddition of ketene silyl acetals to C{sub 60} occurs efficiently under irradiation of the visible light in benzene as well as benzonitrile to yield the fullereneacetates. The comparison of the observed rate constants determined from the dependence of the quantum yields on the concentrations of ketene silyl acetals as well as the quenching of triplet excited state of C{sub 60} by ketene silyl acetals with those predicted for the electron transfer processes indicates that the photoaddition proceeds via photoinduced electron transfer from ketene silyl acetals to the triplet excited state of C{sub 60}. The negative shift in the one-electron reduction potentials by the adduct formation of C{sub 60} is examined by the cyclic voltammetry measurements. The factors to control the formation of mono- and bisadducts of C{sub 60} are clarified based on the rates of photoinduced electron transfer from ketene silyl acetals to the triplet excited states of C{sub 60} and the adducts. 40 refs., 7 figs., 2 tabs.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 159687
- Journal Information:
- Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 45 Vol. 117; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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