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1,4,5,8‐Tetraethynylanthracene – Synthesis, UV/Vis Absorption Spectroscopy and its Application as Building Block for Tetradentate Acceptor Molecules
Author(s) -
Niermeier Philipp,
Teichmann Lisa,
Neumann Beate,
Stammler HansGeorg,
Mitzel Norbert W.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801317
Subject(s) - chemistry , metalation , sodium borohydride , sodium dithionite , photochemistry , trimethylsilyl , acceptor , absorption spectroscopy , molecule , ultraviolet visible spectroscopy , inorganic chemistry , organic chemistry , catalysis , physics , quantum mechanics , condensed matter physics
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.