Preparation and characterisation of two [70]fullerene diols, C70Ph8(OH)2

Abstract

Reaction of a CCl₄ solution of C₇₀Ph₈ with air in the presence of light and [70]fullerene gives a bis-lactone C₇₀Ph₈O₄ (44%), together with a 1,2-diol, C₇₀Ph₈(OH)₂, 19,26,33,37,45,49,53,63-octaphenyl-7,8,19,26,33,37,45,49,53,63-decahydro[70]fullerene-7,8-diol (40%), 1 of C_s symmetry. This latter is also produced from reaction of a dichloromethane solution of C₇₀Ph₈ with 18-crown-6 and KMnO₄, together with another C_s symmetry diol, 2, two possible structures for which are proposed; both 1 and 2 are the first diols to be derived from [70]fullerene. Whereas 1 is very insoluble in most organic solvents (but dissolves in THF), 2 is readily soluble in many organic solvents such as toluene, benzene, chloroform, carbon disulfide, and THF. The derivatives show appreciable differences in both their NMR spectra and their EI mass spectrometry fragmentation patterns.