Synthesis of polyphosphodiesters by ring-opening polymerization of cyclic phosphates bearing allyl phosphoester protecting groups

Benoit Clement, Daniel G. Molin, Christine Jerome, Philippe Lecomte*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

12 Citations (Web of Science)

Abstract

The allyl phosphoester group is shown to be a protecting group for the synthesis of anionic polyphosphodiesters. Our strategy relies on the synthesis of a cyclic phosphate monomer bearing a pendant allyl phosphoester group, its easy purification by fractional distillation, its organocatalyzed ring-opening polymerization by 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) and 1-[3,5-bis(trifluoromethyl)phenyl]-3-cyclohexyl-thiourea (TU). Finally, the deprotection of the allyl phosphoester group is carried out by reaction with sodium benzenethiolate in the absence of any detectable degradation.
Original languageEnglish
Pages (from-to)2642-2648
JournalJournal of Polymer Science Part A-Polymer Chemistry
Volume53
Issue number22
DOIs
Publication statusPublished - 15 Nov 2015

Keywords

  • aliphatic polyphosphodiesters
  • biodegradable
  • cyclic phosphate
  • degradable polymer
  • organocatalysis
  • polyelectrolytes
  • ring-opening polymerization
  • water-soluble polymers

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