Photolytic release of bioactive carboxylic acids from fused pyran conjugates

New ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiatio...

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Bibliographic Details
Main Author: Conceição, Rafaela (author)
Other Authors: Hungerford, Graham (author), Costa, Susana P. G. (author), Gonçalves, M. Sameiro T. (author)
Format: article
Language:eng
Published: 2018
Subjects:
Online Access:http://hdl.handle.net/1822/49045
Country:Portugal
Oai:oai:repositorium.sdum.uminho.pt:1822/49045
Description
Summary:New ester cages bearing the coumarin (2H-benzopyran-2-one) skeleton with extended π-systems as phototriggers, for glycine and β-alanine, as models of carboxylic acid bifunctional molecules with biological relevance, were evaluated under photolysis conditions at 254, 300, 350 and 419 nm of irradiation in a RPR-100 photochemical reactor. The processes were followed by HPLC-UV detection and 1H NMR with collection of kinetic data. The results showed a correlation between the photolysis efficiency and the increasing extension of the conjugation for both glycine and β-alanine, showing that the 7-aminocoumarin afforded the best results at all wavelengths tested. From a study of the time-resolved fluorescence behaviour, these compounds were also found to exhibit more complex fluorescence decay kinetics. This was attributed to the presence of conjugated and non-conjugated coumarin species.