Polyyne cyclization to form carbon cages: [16.16.16](1,3,5)cyclophanetetracosayne derivatives C60H6 and C60Cl6 as precursors to C60 fullerene

Article abstract of DOI:10.1016/S0040-4020(01)00250-2

[16.16.16](1,3,5)Cyclophanes fused by six [4.3.2]propellatriene units, which would serve as precursors to cage polyyne C₆₀H₆ and its perchloro derivative C₆₀Cl₆, respectively, were prepared. In the negative mode laser desorption mass spectra of the cyclophanes, the polyyne anions C₆₀H₆^- and C₆₀Cl₆^- were detected. Moreover, size-selective formation of C₆₀⁺ as well as C₆₀^- was also observed, indicating the possible polyyne cyclization mechanism to form the fullerene cage.