Bouquet-type dendrimerlike poly(ethylene oxide)s with a focal aldehyde and peripheral hydroxyls

Xiaoshuang Feng, Daniel Taton*, Elliot L. Chaikof, Yves Gnanou

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Doubly functionalized dendrimerlike poly(ethylene oxide)s (PEOs) carrying 16 hydroxyl groups at their periphery and one aldehyde group at their focal point were synthesized up to the fourth generation through an iterative divergent approach. First, a protected aldehyde dihydroxyl compound, namely, 3,3-diethoxy-1,2-propanediol, was used as initiator for the anionic ring-opening polymerization (AROP) of ethylene oxide after partial deprotonation (30%) in dimethyl sulfoxide. The two hydroxyls carried by the PEO chain ends of the first generation were subsequently derivatized so as to generate four hydroxyls via a two-step reaction (allylation and osmylation). The next generations of such dendrimerlike PEOs were grown upon repeating the same cycle of AROP and chain-end modification. At the completion of these reactions, the acetal group present at the core was deprotected under acidic conditions to afford the targeted dendrimerlike PEO of fourth generation with a central aldehyde group. The reactivity and accessibility of the latter function was demonstrated upon its conjugation with aniline used as a model compound.

Original languageEnglish (US)
Pages (from-to)2374-2378
Number of pages5
JournalBiomacromolecules
Volume8
Issue number8
DOIs
StatePublished - Aug 1 2007

ASJC Scopus subject areas

  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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