Sequential Uncaging with Green Light can be Achieved by Fine-Tuning the Structure of a Dicyanocoumarin Chromophore

Albert Gandioso, Marta Palau, Alba Nin-Hill, Ivanna Melnyk, Carme Rovira, Santi Nonell, Dolores Velasco, Jaume García-Amorós, Vicente Marchán

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26 Cites (Scopus)

Resum

We report the synthesis and photochemical properties of a series of dicyanocoumarinylmethyl (DEAdcCM)- and dicyanocoumarinylethyl (DEAdcCE)-based photocages of carboxylic acids and amines with absorption maximum around 500 nm. Photolysis studies with green light have demonstrated that the structure of the coumarin chromophore as well as the nature of the leaving group and the type of bond to be photocleaved (ester or carbamate) have a strong influence on the rate and efficiency of the uncaging process. These experimental observations were also supported by DFT calculations. Such differences in deprotection kinetics have been exploited to sequentially photolyze two dicyanocoumarin-caged model compounds (e.g., benzoic acid and ethylamine), and open the way to increasing the number of functional levels that can be addressed with light in a single system, particularly when combining dicyanocoumarin caging groups with other photocleavable protecting groups, which remain intact under green light irradiation.

Idioma originalAnglès
Pàgines (de-a)375-384
Nombre de pàgines10
RevistaChemistryOpen
Volum6
Número3
DOIs
Estat de la publicacióPublicada - 1 de juny 2017

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