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A Convergent Approach to Biocompatible Polyglycerol “Click” Dendrons for the Synthesis of Modular Core–Shell Architectures and Their Transport Behavior
Author(s) -
Wyszogrodzka Monika,
Haag Rainer
Publication year - 2008
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.200800892
Subject(s) - dendrimer , bifunctional , click chemistry , biocompatible material , cycloaddition , materials science , convergent synthesis , combinatorial chemistry , chemistry , chemical engineering , polymer chemistry , organic chemistry , catalysis , medicine , biomedical engineering , engineering
Dendrimers are an important class of polymeric materials for a broad range of applications in which monodispersity and multivalency are of interest. Here we report on a highly efficient synthetic route towards bifunctional polyglycerol dendrons on a multigram scale. Commercially available triglycerol ( 1 ), which is highly biocompatible, was used as starting material. By applying Williamson ether synthesis followed by an ozonolysis/reduction procedure, glycerol‐based dendrons up to the fourth generation were prepared. The obtained products have a reactive core, which was further functionalized to the corresponding monoazido derivatives. By applying copper(I)‐catalyzed 1,3‐dipolar cycloaddition, so‐called “click” coupling, a library of core–shell architectures was prepared. After removal of the 1,2‐diol protecting groups, water‐soluble core–shell architectures 24 – 27 of different generations were obtained in high yields. In the structure–transport relationship with Nile red we observe a clear dependence on core size and generation of the polyglycerol dendrons.