Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation

Lamm J-H, Glatthor J, Weddeling J-H, Mix A, Chmiel J, Neumann B, Stammler H-G, Mitzel NW (2014)
Organic & Biomolecular Chemistry 12(37): 7355-7365.

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Abstract / Notes
A series of bis- and tris[(trimethylsilyl)ethynyl]anthracenes (1,5-, 1,8-, 9,10- and 1,8,10-)has been synthesised by multistep (cross coupling)reactions and the behaviour of the SiMe3-functionalised alkynylanthracene derivatives towards UV irradiation was qualitatively studied by NMR spectroscopy. In the case of 9,10- bis[(trimethylsilyl)ethynyl]anthracene we observed a photodimerisation upon UV irradiation; the third example was reported for a symmetrically 9,10-difunctionalised anthracene derivative, besides those with small fluorine- and methyl-substituents. The anthracene dimerisation is completely thermally reversible and the temperature dependence of the cycloelimination reaction was studied by H-1 VT-NMR experiments. The (deprotected)1,5- and 1,8-diethynylanthracenes were converted with (dimethylamino)-trimethylstannane to obtain the corresponding SnMe3-functionalised alkynes, potentially useful as highly conjugated building blocks in Stille cross coupling reactions. The new anthracene compounds were completely characterised by multinuclear NMR spectroscopy, (high resolution)mass spectrometry and - in most cases - by X-ray diffraction experiments.
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Lamm J-H, Glatthor J, Weddeling J-H, et al. Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation. Organic & Biomolecular Chemistry. 2014;12(37):7355-7365.
Lamm, J. - H., Glatthor, J., Weddeling, J. - H., Mix, A., Chmiel, J., Neumann, B., Stammler, H. - G., et al. (2014). Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation. Organic & Biomolecular Chemistry, 12(37), 7355-7365. doi:10.1039/c4ob00735b
Lamm, J. - H., Glatthor, J., Weddeling, J. - H., Mix, A., Chmiel, J., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2014). Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation. Organic & Biomolecular Chemistry 12, 7355-7365.
Lamm, J.-H., et al., 2014. Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation. Organic & Biomolecular Chemistry, 12(37), p 7355-7365.
J.-H. Lamm, et al., “Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation”, Organic & Biomolecular Chemistry, vol. 12, 2014, pp. 7355-7365.
Lamm, J.-H., Glatthor, J., Weddeling, J.-H., Mix, A., Chmiel, J., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation. Organic & Biomolecular Chemistry. 12, 7355-7365 (2014).
Lamm, Jan-Hendrik, Glatthor, Johanna, Weddeling, Jan-Henrik, Mix, Andreas, Chmiel, Jasmin, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Polyalkynylanthracenes - syntheses, structures and their behaviour towards UV irradiation”. Organic & Biomolecular Chemistry 12.37 (2014): 7355-7365.
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