Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 9, Pages 1768-1773Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101702
Keywords
Photochromism; Chromene; Benzopyran; Photolysis; Kinetics
Categories
Funding
- FCT (Portugal's Foundation for Science and Technology) [SFRH/BPD/65507/2009]
- FEDER through the research unit Centro de Quimica-Vila Real [POCTI-SFA-3-616, PTDC/QUI/66012/2006]
- Region Nord-Pas de Calais (France)
- Ministere de la Jeunesse de l'Education Nationale et de la Recherche (MJENR)
- Fonds Europeens de Developpement Regional (FEDER)
- Fundação para a Ciência e a Tecnologia [PTDC/QUI/66012/2006, SFRH/BPD/65507/2009] Funding Source: FCT
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A new photochromic fused 2H-chromene that has a dehydropyran bridge between the pyran double bond and the benzene ring was prepared. Unlike standard 2H-chromenes that give rise to two coloured species (one short- and one long-lived) under UV irradiation, flash photolysis studies on this particular 2H-chromene show that the opening of the pyran ring led to the formation of a single, coloured, open species that bleaches to the uncoloured initial form in <1 ms. The design of this fused 2H-chromene avoids the formation of the undesirable long-lived, transoidtrans, coloured, open form; therefore, the colour fades very quickly, according to monoexponential kinetics, without the persistence of any residual colour commonly observed in 2H-chromenes. Acid treatment of 4-[(ethoxycarbonyl)methyl]-2H-chromenes led to the formation of lactones.
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