Issue 37, 2014

Polyalkynylanthracenes – syntheses, structures and their behaviour towards UV irradiation

Abstract

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 1H 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.

Graphical abstract: Polyalkynylanthracenes – syntheses, structures and their behaviour towards UV irradiation

Supplementary files

Article information

Article type
Paper
Submitted
07 Apr 2014
Accepted
24 Jul 2014
First published
25 Jul 2014

Org. Biomol. Chem., 2014,12, 7355-7365

Author version available

Polyalkynylanthracenes – syntheses, structures and their behaviour towards UV irradiation

J. Lamm, J. Glatthor, J. Weddeling, A. Mix, J. Chmiel, B. Neumann, H. Stammler and N. W. Mitzel, Org. Biomol. Chem., 2014, 12, 7355 DOI: 10.1039/C4OB00735B

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