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Disassembly Kinetics of Quinone‐Methide‐Based Self‐Immolative Spacers that Contain Aromatic Nitrogen Heterocycles
Author(s) -
Alouane Ahmed,
Labruère Raphaël,
Silvestre Katherine J.,
Le Saux Thomas,
Schmidt Frédéric,
Jullien Ludovic
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201400051
Subject(s) - kinetics , chemistry , quinone methide , pyrimidine , ring (chemistry) , photochemistry , stereochemistry , quinone , organic chemistry , physics , quantum mechanics
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.