Switching Diarylethenes Reliably in Both Directions with Visible Light

A diarylethene photoswitch was covalently connected to two small triplet sensitizer moieties in a conjugated and nonconjugated fashion and the photochromic performance of the resulting compounds was investigated. In comparison with the parent diarylethene (without sensitizers) and one featuring satu...

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Veröffentlicht in:Angewandte Chemie International Edition 2016-01, Vol.55 (3), p.1208-1212
Hauptverfasser: Fredrich, Sebastian, Göstl, Robert, Herder, Martin, Grubert, Lutz, Hecht, Stefan
Format: Artikel
Sprache:eng
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Zusammenfassung:A diarylethene photoswitch was covalently connected to two small triplet sensitizer moieties in a conjugated and nonconjugated fashion and the photochromic performance of the resulting compounds was investigated. In comparison with the parent diarylethene (without sensitizers) and one featuring saturated linkages, the conjugated photoswitch offers superior fatigue resistance upon visible‐light excitation due to effective triplet energy transfer from the biacetyl termini to the diarylethene core. Our design makes it possible to switch diarylethenes with visible light in both directions in a highly efficient and robust fashion based on extending π‐conjugation and by‐product‐free ring‐closure via the triplet manifold. Flipping the spin: When biacetyl triplet sensitizers were linked to a dithienylethene core in a conjugated fashion, the photoswitching performance dramatically improved. This design makes it possible to switch diarylethenes with visible light in both directions in a highly efficient and robust fashion.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201509875