Synthesis of a photochromic fused 2<i>H</i>-Chromene capable of generating a single coloured species

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, transoid-trans, 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.

Data and Resources

Additional Info

Field Value
Source ISSN: 1434-193X
Author Sousa, C.M., Pina, J., Seixas de Melo, J., Berthet, J., Delbaere, S., Coelho, P.J.
Maintainer CCSD
Last Updated May 16, 2026, 12:37 (UTC)
Created May 16, 2026, 12:37 (UTC)
Identifier hal-00702873
Language en
contributor Centro de Química ; Universidade de Trás-os-Montes e Alto Douro - Vila Real
creator Sousa, C.M.
date 2012-05-16T00:00:00
harvest_object_id f13fab03-14bf-4207-a32e-607c400ed3bd
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2025-11-20T00:00:00
relation info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201101702
set_spec type:ART