Thermolysis and Photolysis of C60 Diozonides

• Published in: Fullerenes, nanotubes, and carbon nanostructures Vol. 13; no. 1; pp. 73 - 88
• Main Authors: Heymann, Dieter, Bachilo, Sergei M., Aronson, Sem
• Format: Journal Article
• Language: English
• Published: Taylor & Francis Group 01.01.2005
• Subjects: diepoxides; dioxidoannulenes; diozonides; oxyozonides; Photolysis; Thermolysis; UV-Vis spectra
• ISSN: 1536-383X; 1536-4046
• DOI: 10.1081/FST-200040764

Ozonation of C 60 in o-xylene produced three C 60 (O 3 ) 2 diozonides that were separated from one another and from two C 60 (O 3 ) 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 C 60 O(O 3 ) oxyozonide, then to a C 60 O 2 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 C 60 O 2 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.