2026-04-13T18:30:29Zhttps://recercat.cat/oai/request

oai:recercat.cat:2445/1140292025-12-04T21:44:06Zcom_2072_1057col_2072_478917col_2072_478933

00925njm 22002777a 4500 dc Gandioso, Albert author Palau Requena, Marta author Nin-Hill, Alba author Melnyk, Ivanna author Rovira i Virgili, Carme author Nonell, Santi author Velasco Castrillo, Dolores author Garcia Amorós, Jaume author Marchán Sancho, Vicente author 2017-07-19T08:16:21Z 2017-07-19T08:16:21Z 2017-07 2017-07-19T08:16:21Z 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. Llum Fotoquímica Síntesi orgànica Cumarines Light Photochemistry Organic synthesis Coumarins Sequential uncaging with green light can be achieved by fine-tuning the structure of a dicyanocoumarin chromophore