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Title: Sequential uncaging with green light can be achieved by fine-tuning the structure of a dicyanocoumarin chromophore
Author: Gandioso, Albert
Palau Requena, Marta
Nin-Hill, Alba
Melnyk, Ivanna
Rovira i Virgili, Carme
Nonell, Santi
Velasco Castrillo, Dolores
Garcia Amorós, Jaume
Marchán Sancho, Vicente
Keywords: Llum
Síntesi orgànica
Organic synthesis
Issue Date: Jul-2017
Publisher: Wiley-VCH Verlag
Abstract: 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 that remain intact under green light irradiation.
Note: Reproducció del document publicat a:
It is part of: ChemistryOpen, 2017, vol. 6, num. 3, p. 375-384
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ISSN: 2191-1363
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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