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Photochemical Amplifier Based on Self-Immolative Dendritic Spacers

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Author Kastrati Agonist, Bochet Christian G.,
Project Photons in organic synthesis
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Original article (peer-reviewed)

Journal The Journal of Organic Chemistry
Volume (Issue) 84(12)
Page(s) 7776 - 7785
Title of proceedings The Journal of Organic Chemistry
DOI 10.1021/acs.joc.9b00651


A self-immolative dendritic structure was synthesized.  It is based on phenol derivs. with three hydroxymethyl arms at both ortho and para positions of the core unit, potentially releasing up to 27 leaving groups in a third-generation dendrimer.  The triggering event is the photolysis of a photosentive ortho-nitrobenzyl group.  In doing so, we expected to transform a weak chem. or photochem. input into a large chem. output, which fulfills the definition of a mol. amplifier.  Such dendrimers could find application as an indicator, a drug-delivery vector, or a solubilizing agent.  The prepd. dendrimer indeed released up to 27 leaving groups upon photolysis at 360 nm.