Photochromism of a Diarylethene Having an Azulene Ring

Diarylethene derivatives incorporating an azulene ring at the ethene moiety were synthesized. One derivative having thiazole rings showed the expected coloration reaction by excitation at 313 nm (to a higher singlet state) but not when excited at 635 nm (S0 to S1 excitation). The system demonstrates...

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Veröffentlicht in:Journal of organic chemistry 2012-04, Vol.77 (7), p.3270-3276
Hauptverfasser: Kitai, Jun-ichiro, Kobayashi, Takao, Uchida, Waka, Hatakeyama, Makoto, Yokojima, Satoshi, Nakamura, Shinichiro, Uchida, Kingo
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Sprache:eng
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Zusammenfassung:Diarylethene derivatives incorporating an azulene ring at the ethene moiety were synthesized. One derivative having thiazole rings showed the expected coloration reaction by excitation at 313 nm (to a higher singlet state) but not when excited at 635 nm (S0 to S1 excitation). The system demonstrates that the cyclization reaction can be controlled by selective excitation at different wavelengths of the absorption spectrum. On the other hand, another derivative having thiophene rings did not show any photochromism. The results clearly show the importance of the coplanarity of the system for the photoisomerization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo202673z