Geodesic–Planar Conjugates: Substituted Buckybowls – Synthesis, Photoluminescence and Electrochemistry

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 by either Suzuki or Sonogashira cross coupling. 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 ( 9 ) uncovered the formation of 65 % (Idpc) 2 •- as the major reduction product. 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.