Synthesis and first X-ray structure of a hexa-peri-hexabenzocoronene–fullerene-dyad: a model for an inter-carbon-allotrope hybrid

Abstract

The synthesis of a new hexa-peri-hexabenzocoronene (HBC)–fullerene dyad 1 was accomplished involving a covalent linkage between both the planar and the spherical conjugated π-system of the two chromophores. We also present the first X-ray single crystal structure of a HBC–fullerene conjugate. A very short HBC–fullerene distance of 3.2 Å is observed. For the synthesis of this molecule, a new versatile applicable template, namely, a mono-functionalized hexa-peri-hexabenzocoronene 7 was attached to a fullerene. Absorption and fluorescence spectroscopy, as well as quantum yield measurements of 1, indicated close electronic communication between the two subunits, which is promising for possible applications in molecular electronics.