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Dendrimer Disassembly in the Gas Phase: A Cascade Fragmentation Reaction of Fréchet Dendrons
Author(s) -
Baytekin Bilge,
Baytekin H. Tarik,
Hahn Uwe,
Reckien Werner,
Kirchner Barbara,
Schalley Christoph A.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900403
Subject(s) - dendrimer , fragmentation (computing) , chemistry , dissociation (chemistry) , cascade , amine gas treating , ion , collision induced dissociation , electrospray ionization , mass spectrometry , ionization , photochemistry , polymer chemistry , organic chemistry , tandem mass spectrometry , chromatography , computer science , operating system
The mass spectrometric characterization of Fréchet‐type dendrons is reported. In order to provide the charges necessary for electrospray ionization, dendrons bearing an OH group at the focal point can be deprotonated and observed in the negative ion mode. Alternatively, the corresponding bromides can be converted to quaternary ammonium ions that can easily be detected in the positive mode. If the latter ions are subjected to collision‐induced dissociation experiments, a fragmentation cascade begins with the dissociation of the focal amine. The focal benzyl cation quickly decomposes in a fragmentation cascade from the focal point to the periphery until the peripheral benzyl (or naphthylmethyl) cations are formed. Five different mechanisms are discussed in detail, three of which can be excluded based on experimental evidence. The cascade fragmentation is reminiscent of self‐immolative dendrimers.