Affiliation:
1. Universität Bielefeld, Fakultät für Chemie, Lehrstuhl für Anorganische Chemie und Strukturchemie, Centrum für Molekulare Materialien CM2
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.
Funder
Deutsche Forschungsgemeinschaft
Subject
Organic Chemistry,Catalysis
Cited by
5 articles.
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