Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids

Niermeier P, Maibom KAM, Lamm J-H, Neumann B, Stammler H-G, Mitzel NW (2021)
Chemical Science.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Abstract / Bemerkung
Using 2-hydroxypropyl-protecting groups, 1,8-dialkynylanthracene photo-dimers were prepared in head-to-head-configuration by UV irradiation on a multi-gram scale. In non-polar solvents, the combination of non-covalent hydrogen bonds and pi-pi-interactions induces the formation of the syn-isomer in up to 85% yield. Instead, more polar solvents or irradiation of unprotected 1,8-diethynylanthracene led to formation of the corresponding anti-isomer in large excess. Cleavage of the protecting groups under basic conditions affords a rigid hydrocarbon skeleton with four directional functions. This was used as a building block for a tetradentate boron Lewis acid. Its applicability as a host for Lewis-base substrates was demonstrated by the formation of adducts with various nitrogen bases. Adduct formation with hydrazine leads to impressive networks between the tetraboron host and the substrate molecules.
Erscheinungsjahr
2021
Zeitschriftentitel
Chemical Science
ISSN
2041-6520
eISSN
2041-6539
Page URI
https://pub.uni-bielefeld.de/record/2955103

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Niermeier P, Maibom KAM, Lamm J-H, Neumann B, Stammler H-G, Mitzel NW. Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids. Chemical Science. 2021.
Niermeier, P., Maibom, K. A. M., Lamm, J. - H., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2021). Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids. Chemical Science. https://doi.org/10.1039/d1sc02065j
Niermeier, P., Maibom, K. A. M., Lamm, J. - H., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2021). Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids. Chemical Science.
Niermeier, P., et al., 2021. Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids. Chemical Science.
P. Niermeier, et al., “Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids”, Chemical Science, 2021.
Niermeier, P., Maibom, K.A.M., Lamm, J.-H., Neumann, B., Stammler, H.-G., Mitzel, N.W.: Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids. Chemical Science. (2021).
Niermeier, Philipp, Maibom, Kristina A. M., Lamm, Jan-Hendrik, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “Hydrogen-bond-induced selectivity of a head-to-head photo-dimerisation of dialkynylanthracene - access to tetradentate Lewis acids”. Chemical Science (2021).

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