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. 2002 Sep 19;4(19):3247-50.
doi: 10.1021/ol026482w.

Medium-dependent type selectivity in photoreactions of a crown ether-annelated dibenzobarrelene derivative

Heiko Ihmels  1 , Michael Schneider, Michael Waidelich
Affiliations

Medium-dependent type selectivity in photoreactions of a crown ether-annelated dibenzobarrelene derivative

Heiko Ihmels et al. Org Lett. .

Abstract

[reaction: see text] A concept for modifying the photochemical properties of a dibenzobarrelene derivative by the combination of supramolecular assembly and solid-state photochemistry is presented. The irradiation of dibenzobarrelene 1b and alkali metal complexes thereof (1:1) in acetonitrile or benzene solution leads preferentially to the dibenzocyclooctatetraene 4b as the photoproduct. In contrast, the dibenzosemibullvalene 5b is formed as the main photoproduct in the solid state because of a strong cation effect.

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