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Disassembly kinetics of quinone-methide-based self-immolative spacers that contain aromatic nitrogen heterocycles

Chemistry, an Asian journal

Authors: Alouane A, Labruère R, Silvestre KJ, Le Saux T, Schmidt F, Jullien L
Date: 2014-05-01 • Pages: 1334-40 • PMID: 24652669
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We prepared several pyridine- and pyrimidine-based self-immolative spacer groups to evaluate the significance of the resonance energy of the spacer aromatic ring on the kinetics of 1,4- and 1,6-elimination reactions, which govern spacer disassembly. Subsequently, we relied on a photoactivation procedure to accurately analyze the disassembly kinetics. Beyond providing new results that are relevant for deriving quantitative structure-property relationships, herein, we demonstrate that pH value can be used as an efficient parameter to finely control the disassembly time of a self-immolative spacer after an initial activation.