Size-selective formation of C78 fullerene from a three-dimensional polyyne precursor

Multicyclic cagelike cyclophanes 2a and 2b containing cyclobutene rings have been prepared as precursors of three-dimensional polyynes C78H18 (1a) and C78H12Cl6 (1b), respectively. Laser irradiation of 2a and 2b induced expulsion of the aromatic fragment, indane, to give the three-dimensional polyyne anions C78H18- and C78H12Cl6-, respectively. Whereas the former anion lost only four hydrogen atoms to form C78H14-, complete loss of all hydrogen and chlorine atoms was observed from the latter anion, to yield a C-78(-) ion that has a fullerene structure which was proven by its characteristic fragmentation pattern.