1609986-32-4Relevant articles and documents
Disassembly kinetics of quinone-methide-based self-immolative spacers that contain aromatic nitrogen heterocycles
Alouane, Ahmed,Labruere, Raphael,Silvestre, Katherine J.,Le Saux, Thomas,Schmidt, Frederic,Jullien, Ludovic
supporting information, p. 1334 - 1340 (2014/05/06)
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. Burn rubber: Kinetic analysis of the pH-dependent disassembly of self-immolative spacers that contain aromatic nitrogen heterocycles was performed. Electron-poor pyrimidine cores exhibited the longest disassembly times. This study confirms the trend that electron-rich aryl cores accelerate self-immolation.