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Thermolysis and Photolysis of C60 Diozonides

Abstract Ozonation of C60 in o‐xylene produced three C60(O3)2 diozonides that were separated from one another and from two C60(O3)3 triozonides by High Performance Liquid Chromatography (HPLC). Upon thermolysis at 10, 15, and 16.6°C, each of the diozonides dissociated sequentially, first to a C60O(O3) oxyozonide, then to a C60O2 diepoxide. The three diepoxides were stable in solution for at least 3 weeks. The mean lifetimes of the three diozonides were 52 ± 5, 62 ± 6, and 17.3 ± 1.8 min, respectively (all at 15°C). The mean lifetimes of the three oxyozonides were 69.7 ± 0.7 and 58 ± 6 min at 16.6°C, respectively and about 240 min at 10°C. Photolysis of the diozonides yielded two dioxidoannulenes with UV‐Vis adsorption maxima at 333 and 332 nm, and what appeared to be an epoxide‐oxidoannulene with UV‐Vis adsorption maximum at 327 nm. These annulenes were observed to form dimers. We have synthesized and characterized six C60O2 dioxides, at least three and possibly four of which were hitherto unknown. We report the discovery of oxyozonides that form during the dissociation of diozonides.