SYNTHESIS OF 1,4-DIPOLYSTYRYLDIHYDRO[60]FULLERENES BY USING 2,2,6,6-TETRAMETHYL-1-POLYSTYROXYPIPERIDINE AS A RADICAL SOURCE

This is the first report of the synthesis of well-defined disubstitute d polymer derivatives of C-60 by a radical mechanism. Narrow-polydispe rsity polystyryl adducts with TEMPO (2,2,6,6-tetrametylpiperidinyl-1-o xy), prepared by the nitroxyl-mediated ''living'' radical polymerizati on technique, were heated with a 4-fold excess (in molar ratio) of C-6 0 in o-dichlorobenzene at 145 degrees C to give 1,4-dipoly-styryldihyd ro[60]fullerenes (yields 60-80%). A low-mass model compound 2-benzoylo xy-1-phenylethyl adduct with TEMPO gave essentially the same result. T hese disubstituted derivatives retained the redox properties of C-60 a nd gave UV-vis spectra characteristic of 1,4-bisadducts. A possible me chanism by which disubstituted derivatives are selectively produced wa s discussed.