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Issue 37, 2014
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Polyalkynylanthracenes – syntheses, structures and their behaviour towards UV irradiation

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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

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Publication details

The article was received on 07 Apr 2014, accepted on 24 Jul 2014 and first published on 25 Jul 2014


Article type: Paper
DOI: 10.1039/C4OB00735B
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Citation: Org. Biomol. Chem., 2014,12, 7355-7365

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    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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