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Wavelength-selective caged surfaces: how many functional levels are possible?

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2011
Author San Miguel Verónica, Bochet Christian G, del Campo Aránzazu,
Project Photons in organic synthesis
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Original article (peer-reviewed)

Journal Journal of the American Chemical Society
Volume (Issue) 133(14)
Page(s) 5380 - 8
Title of proceedings Journal of the American Chemical Society
DOI 10.1021/ja110572j


The possibility of wavelength-selective cleavage of seven photolabile caging groups from different families has been studied. Amine-, thiol-, and carboxylic-terminated organosilanes were caged with o-nitrobenzyl (NVOC, NPPOC), benzoin (BNZ), (coumarin-4-yl)methyl (DEACM), 7-nitroindoline (DNI, BNI), and p-hydroxyphenacyl (pHP) derivatives. Caged surfaces modified with the different chromophores were prepared, and their photosensitivity at selected wavelengths was quantified. Different pairs, trios, and quartets of chromophore combinations with wavelength-selective photoresponse were identified. Our results show, for the first time, the possibility of generating surfaces with up to four different and independently addressable functional levels. In addition, this manuscript presents the first systematic comparison of the photolytic properties of different photolabile groups under different irradiation conditions.