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.
Keywords: C−C coupling; electrochemistry; fluorescence; polycyclic aromatic hydrocarbons; strained molecules.
© 2020 The Authors. Published by Wiley-VCH GmbH.