Photoinduced electron transfer alcohols, formation

Some cation radicals can appear as hydrogen acceptors. Thus, fullerene C6o is oxidized to the cation radical at preparative scale by means of photoinduced electron transfer. This cation radical reacts with various donors of atomic hydrogen (alcohols, aldehydes, ethers), yielding the fullerene 1,2-dihydroderivative. In the case of tert-butanol, propionic acid, and glycol, product formation is also initiated by H abstraction from the OH group. The reaction proceeds according to Scheme 1-47 (Siedschlag et al. 2000) ... 

Compared with alcohols, which possess a high standard potential of oxidation, moderate nucleophilicity and weak basicity, amines very often serve as good electron donors and relatively strong bases and nucleophiles in chemical reactions. Photoinduced electron transfer (PET) processes, in which an amine donates an electron to the reaction partner in either its ground or excited electronic state, result in the formation of an amine substrate exciplex (Scheme 6.196).670 1224 The driving force for electron transfer is related to the standard potential of oxidation of the donor, the standard potential of reduction of the acceptor and the excited state energy of the absorbing partner (see Chapter 4). 

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