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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Abstract
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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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.
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.
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