Through-Space Control of the Persistence of Photogenerated o-Quinonoid Intermediates in Naphthalenes Containing Cofacially Oriented Chromenes and Arenes

Remarkable modulation of the persistence of the photogenerated colored o-quinonoid intermediates via a through-space interaction has been demonstrated in chromenes 1–4 based on 1,8-diarylnaphthalenes. Polar/π interaction is shown to stabilize the closed form of 4 to such an extent that photoinduced...

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Bibliographic Details
Published in:Organic letters 2012-05, Vol.14 (10), p.2438-2441
Main Authors: Moorthy, Jarugu Narasimha, Mandal, Susovan, Parida, Keshaba Nanda
Format: Article
Language:English
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Summary:Remarkable modulation of the persistence of the photogenerated colored o-quinonoid intermediates via a through-space interaction has been demonstrated in chromenes 1–4 based on 1,8-diarylnaphthalenes. Polar/π interaction is shown to stabilize the closed form of 4 to such an extent that photoinduced coloration is virtually invisible, while the same stabilization in the opened form of 2 permits ready coloration with a long-lived o-quinonoid intermediate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300449p