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(Invited) C70 As a Photocatalyst for Oxidation of Benzylamines to Imines

Wednesday, 1 June 2016: 16:40
Aqua 311 A (Hilton San Diego Bayfront)
R. Kumar and Y. Yamakoshi (ETH Zürich)
Photosensitivity is one of the most important physico-chemical properties of fullerenes. Photoexcited C60 and C70 can cause the electron transfer (type I)1 or energy transfer (type II)2,3 reaction under visible light irradiation in quite high quantum yields (quantitative). These reactions have been used to develop new functional materials for the application of photovoltaic devices and photodynamic therapy agents. Especially in the latter application, generation of reactive oxygen species (ROSs)4 such as 1O2 and O25,6is used to affect the biological molecules.

The generation of 1O2 has been also used in the organic reaction. Using fullerenes as photocatalyst, oxidation of olefins,7 phenols8 and sulfides9 were reported. In this study, we used C70 for the oxidation of benzylamines. Compared to C60 and other commonly used photosensitizers such as tetraphenylporphyrin (TPP),10,11 C70 could catalyze the oxidation of benzylamines to corresponding imines efficiently with lower catalyst loading (0.01 mol %). The reaction worked also under the lower energy of lights using blue (max 470 nm) and green (max 520 nm) diodes. Reaction processed in clean manner without any significant amount of side product, and removal of the C70catalyst was carried out easily by just simple precipitation and filtration.

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