Structure Determination and Electrochemistry of Products from the Radical Reaction of C60 with Azo(bisisobutyronitrile)

Thermal decomposition of azo(bisisobutyronitrile) in a 1,2-dichlorobenzene solution of C 60 gave three regioisomeric 1, x -di(2-cyano-2-propyl)-1, x -dihydro[60]fullerenes in 12, 2, and 4% yields, assigned as the 1,4-, 1,2-, and a third isomer of still uncertain structure. The 1,4- and unidentified isomers underwent three reversible reduction steps by cyclic voltammetry, and UV−vis−NIR spectra of the mono- and dianions generated electrochemically were recorded. The first two redox potentials of the 1,4-isomer were the same as those of C 60, but those of the third isomer were positively shifted by 0.23 and 0.21 V from those of C 60, showing that it is an electron-deficient derivative of C 60 .