Geodesic-Planar Conjugates: Substituted Buckybowls—Synthesis, Photoluminescence and Electrochemistry

Abstract

C−C cross coupling products of bowl-shaped as-indaceno[3,2,1,8,7,6-pqrstuv]picene (Idpc) and different planar arenes and ethynyl-arenes were synthesized. Photoluminescence as well as electrochemical properties of all products were investigated and complemented by time-dependent quantum chemical calculations. UV/Vis spectroelectrochemistry investigations of the directly linked (Idpc)2 indicated the absence of any intramolecular charge-transfer transition of intermittently formed (Idpc)2.−. All coupling products showed fluorescence. Ferrocene-1-yl-Idpc was structurally characterized by X-ray diffraction and is a rare example of a ferrocene-containing buckybowl exhibiting luminescence.