Formation of fullerenes by pyrolysis of 1,2′-binaphthyl and 1,3-oligonaphthylene

High-temperature pyrolysis of two fullerene precursors – 1,2′-binaphthyl and 1,3-oligonaphthyl – has been investigated. An oligomer of naphthalene with the appropriate orientation of fragments, which contains all 60 carbon atoms, 12 of 20 six-membered rings and 71 of 90 carbon–carbon bonds required to form the C60 fullerene cage was synthesized in a three-step synthesis from naphthalene. The formation of fullerene during pyrolysis was confirmed by MALDI-TOF and HPLC analysis of the toluene extract obtained from the raw soot. It was found that the toluene extract contains free C60 fullerene but the main share of fullerenes exists in the form of their derivatives. The yield of free C60 was estimated as 0.1% by HPLC but the overall yield of C60 seems to be higher and was estimated as ≈1%.