4 years ago

From Bidentate Gallium Lewis Acids to Supramolecular Complexes

From Bidentate Gallium Lewis Acids to Supramolecular Complexes
Norbert W. Mitzel, Andreas Mix, Beate Neumann, Jan Horstmann, Mentor Hyseni, Hans-Georg Stammler
Bidentate gallium Lewis acids were prepared by the reaction of diethynyldiphenylsilane with neat trimethyl- or triethylgallium. Bis[(dimethylgallyl)ethynyl]diphenylsilane (1) and diethylgallyl derivative 2 were characterized as Et2O or pyridine adducts by NMR spectroscopy; 2⋅2Py was isolated. Lewis acids 1 and 2 form host–guest adducts with bidentate nitrogen bases, but defined cyclic 1:1 adducts are only formed between 1 and bases with matching N⋅⋅⋅N distances: 4,4′-dimethyl-3,3′-bipyridinylacetylene (3), bis[(pyridin-3-yl)ethynyl]diphenylsilane (4), and bis[(2-methylpyridin-5-yl)ethynyl]diphenylsilane (5). The structures of adducts 1⋅3, 1⋅4, and 1⋅5 were established by X-ray diffraction experiments. 2⋅2Py reacts with DABCO to afford polymeric (DABCO-2-)n. Matchmaking: Supramolecular host–guest formation between the bidentate Lewis acid bis[(dialkylgallyl)ethynyl]diphenylsilane (alkyl=Me, Et) with defined Ga⋅⋅⋅Ga distances and tailor-made bidentate pyridine bases with various N⋅⋅⋅N distances were studied. An insufficient match of the distances leads to either no reaction or polymeric compounds, while a good match gives defined cyclic 1:1 adducts.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201701303

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