Formation of Carbon Nanotube Based Gears: Quantum Chemistry and Molecular Mechanics Study of the Electrophilic Addition of o-Benzyne to Fullerenes, Graphene, and Nanotubes

Considerable progess has been made in recent years in chemical functionalization of fullerene molecules [see, for example: Taylor 93, and Diederich 96]. In some cases, the predominant reaction products are different from those obtained (using the same reactants) from polycyclic aromatic hydrocarbons (PAHs). One such example is the cycloaddition of o-benzyne to C60. It is well established that benzyne (Fig. 1) adds across one of the rings in naphthalene, anthracene and other PAHs [Hoffmann 67] forming the [2 +4] cycloaddition product (benzobicyclo[2.2.2.]-octatriene with naphthalene and triptycene with anthracene (Fig. 2)). However, Hoke et al [Hoke 92]