Oxazoline and Imidazoline Functionalization of a C60 Dimer via the Reaction of C60HBn and Aromatic Nitriles with a Bifunctional Hydroxide.

Oxazoline and imidazoline functionalization of a singly bonded C60 dimer is achieved via a one-pot reaction of C60HBn with OH- and aromatic nitriles, where the OH- not only functions as a Brønsted base that deprotonates C60HBn but also as a nucleophile that initiates the nucleophilic addition to the fullerene cage. The structures of the obtained oxazolinated and imidazolinated C60 dimeric compounds have been established by HRMS, UV--vis, and ¹H, 13C, and HMBC NMR characterizations and computational calculations. The reaction mechanism is studied with the in situ vis-near-IR spectra, which shows that the use of I2 is crucial for the functionalization of the C60 dimer, indicating that it is likely the dimeric molecule rather than the fragment of the dimer that is involved in the reaction. [ABSTRACT FROM AUTHOR]