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Exploring the photoinduced electron transfer reactivity of aza[60]fullerene iminium cation
Authors:Manolis M Roubelakis  Leanne C Nye  Michael Orfanopoulos
Institution:
  • a Department of Chemistry, University of Crete, Campus Voutes, Heraklion 71003, Greece
  • b Institute of Physical Chemistry, NCSR ‘Demokritos’, Agia Paraskevi Attikis, Athens 15310, Greece
  • c Department of Chemistry and Pharmacy, University of Erlangen-Nurnberg, Erlangen D-91058, Germany
  • Abstract:Photolysis of (C59N)2 solutions in the presence of neutral π-donors, such as arenes and electron-rich alkenes leads to a series of novel aza60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza60]fullerene, followed by radical coupling of the resulting aza60]fullerenyl radical with an intermediate stabilized radical derived from the substrate. This type of reactivity has been proven efficient with arenes having oxidation potential higher than about 1.5 V. Simple olefins, such as tri- and tetra-methylethylene, as well as cyclohexene, can also participate in this kind of photoinduced electron transfer-initiated reaction with C59N+, affording the corresponding aza60]fullerene derivatives. In the case of 2-methoxyprop-1-ene, 2,4-hexadiene, and β,β-dimethylstyrene, 2+2] cycloaddition reactions with the aza60]fullerene carbon shell dominate, leading to a mixture of unidentified multiadducts.
    Keywords:Aza[60]fullerene  Photoinduced electron transfer  Iminium cation  Benzyltrimethylsilanes  Electron-rich olefins
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