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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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
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.
Erscheinungsjahr
Zeitschriftentitel
Organic & Biomolecular Chemistry
Band
12
Ausgabe
37
Seite(n)
7355-7365
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PUB-ID

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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.

7 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

A Rational Approach to Tetra-Functional Photo-Switches.
Niermeier P, Lamm JH, Mix A, Neumann B, Stammler HG, Mitzel NW., ChemistryOpen 8(3), 2019
PMID: 30886788
Regiochemical Control in Triptycene Formation-An Exercise in Subtle Balancing Multiple Factors.
Lamm JH, Vishnevskiy YV, Ziemann E, Neumann B, Stammler HG, Mitzel NW., ChemistryOpen 7(1), 2018
PMID: 29344439
Fluoride complexation by bidentate silicon Lewis acids.
Horstmann J, Niemann M, Berthold K, Mix A, Neumann B, Stammler HG, Mitzel NW., Dalton Trans 46(6), 2017
PMID: 28106199
Gas-phase structure of 1,8-bis[(trimethylsilyl)ethynyl]anthracene: cog-wheel-type vs. independent internal rotation and influence of dispersion interactions.
Otlyotov AA, Lamm JH, Blomeyer S, Mitzel NW, Rybkin VV, Zhabanov YA, Tverdova NV, Giricheva NI, Girichev GV., Phys Chem Chem Phys 19(20), 2017
PMID: 28485433
Quantitative Structure-Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl-Substituted Derivatives.
Rouillé G, Jäger C, Huisken F, Henning T, Czerwonka R, Theumer G, Börger C, Bauer I, Knölker HJ., ChemistryOpen 6(4), 2017
PMID: 28794947
1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures.
Lamm JH, Horstmann J, Stammler HG, Mitzel NW, Zhabanov YA, Tverdova NV, Otlyotov AA, Giricheva NI, Girichev GV., Org Biomol Chem 13(33), 2015
PMID: 26204511

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