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DOI: 10.1055/s-0037-1611344
1,8,10-Substituted Anthracenes – Hexafunctional Frameworks via Head-to-Tail Photodimerisation
This work was funded by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) grant number MI 477/25-2, project number 248859450.Publication History
Received: 28 September 2018
Accepted after revision: 23 October 2018
Publication Date:
12 December 2018 (online)
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Abstract
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-to-head isomers. Working under non-inert conditions led to formation of endoperoxides in some cases. Furthermore, a non-classical [4π+2π] 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.
Key words
anthracenes - photodimerisation - endoperoxides - non-classical photodimers - solid-state structuresSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611344.
- Supporting Information
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See, for example:
Examples for [4π+2π] photodimers:
See, for example:
Examples for solid-state structures of 9,10-epidioxyanthracenes:
Examples for solid-state structures of tetracene-based endoperoxides:
For solid-state structures of pentacene-based endoperoxides: