1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures

Lamm J-H, Horstmann J, Stammler H-G, Mitzel NW, Zhabanov YA, Tverdova NV, Otlyotov AA, Giricheva NI, Girichev GV (2015)
Organic & Biomolecular Chemistry 13(33): 8893-8905.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
1,8-Bis(phenylethynyl) anthracene (1,8-BPEA) was synthesized by a twofold Kumada cross-coupling reaction. The molecular structure of 1,8-BPEA was determined using a combination of gas-phase electron diffraction (GED), mass spectrometry (MS), quantum chemical calculations (QC) and single-crystal X-ray diffraction (XRD). Five rotamers of the molecule with different orientations of phenylethynyl groups were investigated by DFT calculations. According to these, molecules of C-2 symmetry with co-directional rotation of the phenylethynyl groups are predicted to exist in the gas phase at 498 K. This was confirmed by a GED/MS experiment at this temperature. The bonding of this conformer was studied and described in terms of an NBO-analysis. Dispersion interactions in the solid state structure and in the free molecule are discussed. In the solid this symmetry is broken; the asymmetric unit of the single crystal contains 3.5 molecules and a herringbone packing motif of pi-stacked dimers and trimers. The pi-stacking in the dimers is between the anthracene units, and the trimers are linked by pi-stacking between phenyl and anthracene units. The interaction between these stacks can be described in terms of sigma(C-H)center dot center dot center dot pi interactions.
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Zeitschriftentitel
Organic & Biomolecular Chemistry
Band
13
Zeitschriftennummer
33
Seite
8893-8905
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Lamm J-H, Horstmann J, Stammler H-G, et al. 1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures. Organic & Biomolecular Chemistry. 2015;13(33):8893-8905.
Lamm, J. - H., Horstmann, J., Stammler, H. - G., Mitzel, N. W., Zhabanov, Y. A., Tverdova, N. V., Otlyotov, A. A., et al. (2015). 1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures. Organic & Biomolecular Chemistry, 13(33), 8893-8905. doi:10.1039/c5ob01078k
Lamm, J. - H., Horstmann, J., Stammler, H. - G., Mitzel, N. W., Zhabanov, Y. A., Tverdova, N. V., Otlyotov, A. A., Giricheva, N. I., and Girichev, G. V. (2015). 1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures. Organic & Biomolecular Chemistry 13, 8893-8905.
Lamm, J.-H., et al., 2015. 1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures. Organic & Biomolecular Chemistry, 13(33), p 8893-8905.
J.-H. Lamm, et al., “1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures”, Organic & Biomolecular Chemistry, vol. 13, 2015, pp. 8893-8905.
Lamm, J.-H., Horstmann, J., Stammler, H.-G., Mitzel, N.W., Zhabanov, Y.A., Tverdova, N.V., Otlyotov, A.A., Giricheva, N.I., Girichev, G.V.: 1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures. Organic & Biomolecular Chemistry. 13, 8893-8905 (2015).
Lamm, Jan-Hendrik, Horstmann, Jan, Stammler, Hans-Georg, Mitzel, Norbert W., Zhabanov, Yuriy A., Tverdova, Natalya V., Otlyotov, Arseniy A., Giricheva, Nina I., and Girichev, Georgiy V. “1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures”. Organic & Biomolecular Chemistry 13.33 (2015): 8893-8905.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

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
Intramolecular π-π Interactions in Flexibly Linked Partially Fluorinated Bisarenes in the Gas Phase.
Blomeyer S, Linnemannstöns M, Nissen JH, Paulus J, Neumann B, Stammler HG, Mitzel NW., Angew Chem Int Ed Engl 56(43), 2017
PMID: 28834050

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