Supramolecular complexation of C60 and C70 by helical nanographene incorporating N-heterotriangulene and hexabenzocoronene subunits

Abstract

Supramolecular host–guest complexes are studied in the gas-phase evaluating a new host molecule for fullerenes (C₆₀ and C₇₀). The new host molecule is a double N-heterotriangulene-[5]helicene (NTH), consisting of two N-heterotriangulene (N-HTA) blades embedded into a hexabenzocoronene-like backbone with helically curved topology. Host–guest complexes of [1:1]⁺˙^/2+, [1:2]⁺˙^/2+, [2:1]²⁺ and [2:3]²⁺ stoichiometry and charge state are formed by electrospray ionization-mass spectrometry (ESI-MS). Ion formation occurs through electrochemical oxidation of the N-HTA moieties. Energy-resolved collision-induced dissociation (ER-CID) experiments reveal the noncovalent binding of the fullerenes to the NTH molecule and provide an order of stability for the complexes. Density-functional theory (DFT) calculations establish the lowest energy geometries of the complexes.