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

Philipp Niermeier; Jan-Hendrik Lamm; Jan-Hendrik Peters; Beate Neumann; Hans-Georg Stammler; Norbert W. Mitzel

doi:10.1055/s-0037-1611344

Synthesis, Table of Contents

Synthesis 2019; 51(07): 1623-1632
DOI: 10.1055/s-0037-1611344

paper

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

Philipp Niermeier

,

Jan-Hendrik Lamm

,

Jan-Hendrik Peters

,

Beate Neumann

,

Hans-Georg Stammler

,

Norbert W. Mitzel*

Universität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2, Universitätsstraße 25, 33615 Bielefeld, Germany Email: mitzel@uni-bielefeld.de

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Abstract

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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 structures

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References

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