Dendritic, Oligomeric, and Polymeric Self-Immolative Molecular Amplification

Michal E. Roth, Ori Green, Samer Gnaim, Doron Shabat*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review


The developments made in the last 12 years or so in the synthesis and application of self-immolative molecules that are based on dendritic, oligomeric, and polymeric structures are reviewed. Two basic disassembly reaction mechanisms are generally employed as tools to construct responsive self-immolative functions, quinone methide eliminations and cyclization reactions. These two tools have been harnessed to design numerous molecular systems that in response to external stimuli undergo programmed disassembly. Systems that allow up to three quinone methide eliminations in one phenol or aniline molecule have opened a door for new branched molecular amplifiers. Such branched molecules can serve as adaptors that achieve release of double or triple payloads in response to a single molecular event. The branched units can be assembled into dendritic structures that disassemble through self-immolative pathways. To further improve this amplification effect, a dendritic chain reaction has been applied. This technique uses simple dendritic molecules to achieve high-generation selfimmolative dendrimers.

Original languageEnglish
Pages (from-to)1309-1352
Number of pages44
JournalChemical Reviews
Issue number3
StatePublished - 10 Feb 2016


FundersFunder number
Focal Technology Area
German Israeli Foundation
Israeli National Nanotechnology Initiative
Leona M. and Harry B. Helmsley Nanotechnology Research Fund
United States-Israel Binational Science Foundation
Israel Science Foundation


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