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Self‐Immolative Spacers: Kinetic Aspects, Structure–Property Relationships, and Applications
Author(s) -
Alouane Ahmed,
Labruère Raphaël,
Le Saux Thomas,
Schmidt Frédéric,
Jullien Ludovic
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201500088
Subject(s) - chemistry , moiety , nanotechnology , covalent bond , drug delivery , cascade , self assembly , cleavage (geology) , combinatorial chemistry , stereochemistry , materials science , organic chemistry , chromatography , fracture (geology) , composite material
Self‐immolative spacers are covalent assemblies tailored to correlate the cleavage of two chemical bonds after activation of a protective part in a precursor: Upon stimulation, the protective moiety is removed, which generates a cascade of disassembling reactions leading to the temporally sequential release of smaller molecules. Originally introduced to overcome limitations for drug delivery, self‐immolative spacers have gained wide interest in medicinal chemistry, analytical chemistry, and material science. For most applications, the kinetics of the disassembly of the activated self‐immolative spacer governs functional properties. This Review addresses kinetic aspects of self‐immolation. It provides information for selecting a particular self‐immolative motif for a specific demand. Moreover, it should help researchers design kinetic experiments and fully exploit the rich perspectives of self‐immolative spacers.