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Well-defined fullerene-PEG conjugates, C 60 -PEG ( 1 ) and two C 70 -PEG ( 2 and 3 with the addition sites on ab- [6,6] and cc- [6,6]-junctions), were prepared from their corresponding Prato monoadduct precursors. The resulting highly water-soluble fullerene-PEG conjugates 1 - 3 were evaluated for their DNA-cleaving activities and reactive oxygen species (ROS) generation under visible light irradiation. Unexpectedly, photoinduced cleavage of DNA by C 60 -PEG 1 was much higher than that by C 70 -PEG 2 and 3 with higher absorption intensity, especially in the presence of an electron donor (NADH). The preference of photoinduced ROS generation from fullerene-PEG conjugates 1 - 3 via the type II (energy transfer) or the type I (electron transfer) photoreaction was found to be dependent on the fullerene core (between C 60 and C 70 ) and functionalization pattern of C 70 (between 2 and 3 ). This was clearly supported by the electron transfer rate obtained from cyclic voltammetry data and computationally estimated relative rate of each step of the type II and the type I reactions, with the finding that type II energy transfer reactions occurred in the inverted Marcus regime while type I electron transfer reactions proceeded in the normal Marcus regime. This finding on the disparity in the pathways of photoinduced reactions ( type I versus type II ) provides insights into the behavior of photosensitizers in water and the design of photodynamic therapy drugs.

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Unexpected Disparity in Photoinduced Reactions of C60 and C70 in Water with the Generation of O2•– or 1O2