Fulleropyrrolidines derived from dioxa- and trioxaalkyl-tethered diglycines

Abstract

Two different alpha,omega-diglicynes linked by linear polyoxaalkyl chains in the presence of formaldehyde underwent Prato reaction to the fullerene C-60. The shorter linker templated formation of only cis-bisadducts, while the longer one afforded a mixture of four bisadducts (all cis and the equatorial) and difullerene dumbbell compound. Their structures were confirmed by the extensive analysis of the spectral data and molecular symmetry, as well. All compounds expressed an ability to arrange into hierarchically ordered supramolecular aggregates, the form of which depended both on the addition pattern and the spacer structure. The attenuated electron-accepting affinity, examined by cyclic voltammetry was in agreement with diminished delocalization of the pi-electronic system. In addition, all compounds exerted a notable radical scavenging activity.