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The Convergent Synthesis of Poly(glycerol‐succinic acid) Dendritic Macromolecules
Author(s) -
Luman Nathanael R.,
Smeds Kimberly A.,
Grinstaff Mark W.
Publication year - 2003
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.200305172
Subject(s) - macromolecule , dendrimer , succinic acid , convergent synthesis , ethylene glycol , polyester , acetal , polymer chemistry , derivatization , glycerol , polymer , materials science , pentaerythritol , chemistry , organic chemistry , biochemistry , fire retardant , high performance liquid chromatography
The high‐yield convergent synthesis of dendrons, dendrimers, and dendritic–linear hybrid macromolecules composed of succinic acid, glycerol, and poly(ethylene glycol) (PEG) is described. This convergent synthesis relies on two orthogonal protecting groups; namely, the benzylidene acetal (bzld) for the protection of the 1,3‐hydroxyls of glycerol and the tert ‐butyldiphenylsilyl (TBDPS) ester for protection of the carboxylic acid of succinic acid. These novel polyester dendritic macromolecules are composed entirely of building blocks known to be biocompatible or degradable in vivo to give natural metabolites. Derivatization of the dendritic periphery with a methacrylate affords a polymer that can be subsequently photo‐cross‐linked. The three‐dimensional cross‐linked gels formed by ultraviolet irradiation are optically transparent, with mechanical properties dependent on the initial cross‐linkable dendritic macromolecule.