Fast and convenient divergent synthesis of aliphatic ester dendrimers by anhydride coupling

Citation
H. Ihre et al., Fast and convenient divergent synthesis of aliphatic ester dendrimers by anhydride coupling, J AM CHEM S, 123(25), 2001, pp. 5908-5917
Citations number
51
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
123
Issue
25
Year of publication
2001
Pages
5908 - 5917
Database
ISI
SICI code
0002-7863(20010627)123:25<5908:FACDSO>2.0.ZU;2-W
Abstract
A novel divergent approach was developed for the synthesis of dendritic ali phatic polyester structures using an acetal-protected anhydride derivative of 2,2-bis(hydroxymethyI)propionic acid as the acylating agent. This diverg ent synthesis is remarkable, because unlike all others, it only requires a small excess of reagent to achieve quantitative growth, and it requires no means of purification other than a simple solvent extraction or precipitati on. A monodisperse sixth generation dendrimer with molecular weight of 30 7 11 Dalton and 192 masked hydroxyl groups was prepared in high yield and pur ity using 1,1,1 -tris(hydroxyphenyl)ethane as the core molecule. Linear and star-shaped poly(ethylene glycol) (PEG) derivatives of narrow polydispersi ty were also used as core molecules in the divergent synthesis of dendritic -linear copolymer hybrids up to the fourth generation without requiring any chromatographic purification.