1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation

Niermeier P, Lamm J-H, Peters J-H, Neumann B, Stammler H-G, Mitzel NW (2019)
SYNTHESIS-STUTTGART 51(7): 1623-1632.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
Several 1,8,10-functionalised anthracene derivatives and a couple of 1,8,9-functionalised anthracene analogous, bearing alkynyl substituents at positions 1 and 8 were synthesised and their photochemistry investigated in UV irradiation experiments. Almost all compounds could be converted into their 9,10: 10', 9'-head-to-tail photodimers completely excluding the formation of the corresponding head-tohead isomers. Working under non-inert conditions led to formation of endoperoxides in some cases. Furthermore, a non-classical [ 4p+ 2p] photodimer was obtained from 1,8,10-tris[(trimethylsilyl) ethynyl] anthracene with one of the alkynyl substituents involved in the photoreaction. The 1H and 13C NMR spectra of all classical and non-classical photodimers were compared with those of the endoperoxides identifying characteristic shifts for the atoms at positions 9 and 10. Moreover, solid-state structures were determined for one or more of each representative.
Erscheinungsjahr
Zeitschriftentitel
SYNTHESIS-STUTTGART
Band
51
Ausgabe
7
Seite(n)
1623-1632
ISSN
eISSN
PUB-ID

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Niermeier P, Lamm J-H, Peters J-H, Neumann B, Stammler H-G, Mitzel NW. 1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation. SYNTHESIS-STUTTGART. 2019;51(7):1623-1632.
Niermeier, P., Lamm, J. - H., Peters, J. - H., Neumann, B., Stammler, H. - G., & Mitzel, N. W. (2019). 1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation. SYNTHESIS-STUTTGART, 51(7), 1623-1632. doi:10.1055/s-0037-1611344
Niermeier, P., Lamm, J. - H., Peters, J. - H., Neumann, B., Stammler, H. - G., and Mitzel, N. W. (2019). 1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation. SYNTHESIS-STUTTGART 51, 1623-1632.
Niermeier, P., et al., 2019. 1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation. SYNTHESIS-STUTTGART, 51(7), p 1623-1632.
P. Niermeier, et al., “1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation”, SYNTHESIS-STUTTGART, vol. 51, 2019, pp. 1623-1632.
Niermeier, P., Lamm, J.-H., Peters, J.-H., Neumann, B., Stammler, H.-G., Mitzel, N.W.: 1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation. SYNTHESIS-STUTTGART. 51, 1623-1632 (2019).
Niermeier, Philipp, Lamm, Jan-Hendrik, Peters, Jan-Hendrik, Neumann, Beate, Stammler, Hans-Georg, and Mitzel, Norbert W. “1,8,10-Substituted Anthracenes - Hexafunctional Frameworks via Head-to-Tail Photodimerisation”. SYNTHESIS-STUTTGART 51.7 (2019): 1623-1632.