1,4,5,8-Tetraethynylanthracene - Synthesis, UV/Vis Absorption Spectroscopy and its Application as Building Block for Tetradentate Acceptor Molecules

摘要

1,4,5,8-Tetraethynylanthracene was synthesised starting from 1,4,5,8-tetrachloroanthracene-9,10-dione. Different reducing agents, namely sodium borohydride, sodium dithionite and zinc, were tested to convert the anthraquinone into the corresponding tetrachloroanthracene. The latter was functionalised in a fourfold Kumada cross-coupling reaction with (trimethylsilyl)- ethynyl substituents, followed by cleavage of the protecting groups using potassium carbonate in methanol. UV/Vis absorption spectroscopy was performed for the highly conjugated tetraalkynyl-substituted anthracenes. In order to demonstrate the usability of 1,4,5,8-tetraethynylanthracene in the field of organometallic chemistry, silicon- and tin-containing (acceptor-)substituents were introduced through (hydro)- metalation reactions. Most of the new compounds were characterised by X-ray diffraction experiments.