Magnesium complexes incorporated by sulfonate phenoxide ligands as efficient catalysts for ring-opening polymerization of ε-caprolactone and trimethylene carbonate

P. O.Sheng Chen, Y. I.Chang Liu, Chia Her Lin, Bao Tsan Ko*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Two novel sulfonate phenol ligands-3, 3′-di-tert-butyl2′- hydroxy-5, 5′,6, 6′-tetramethyl-biphenyl-2-yl 4-X-benzenesulfonate (X=CF3, LCF3 - H, and X=OCH3, L OMe -H)-were prepared through the sulfonylation of 3, 3′-di-tert-butyl-5, 5′, 6, 6′-tetramethylbiphenyl-2, 2′-diol with the corresponding 4-substituted benzenesulfonyl chloride (1 equiv.) in the presence of excess triethylamine. Magnesium (Mg) complexes supported by sulfonate phenoxide ligands were synthesized and characterized structurally. The reaction of MgnBu2 with L-H (2 equiv.) produces the four-coordinated monomeric complexes (LCF3)2Mg (1) and (LOMe)2Mg (2). Complexes 1 and 2 are efficient catalysts for the ring-opening polymerization of ε-caprolactone (ε-CL) and trimethylene carbonate (TMC) in the presence of 9-anthracenemethanol; complex 1 catalyzes the polymerization of ε-CL and TMC in a controlled manner, yielding polymers with the expected molecular weights and narrow polydispersity indices (PDIs). In ε-CL polymerization, the activity of complex 1 is greater than that of complex 2, likely because of the greater Lewis acidity of Mg2+ metal caused by the electron-withdrawing substitute trifluoromethyl (-CF3) at the 4-position of the benzenesulfonate group.

Original languageEnglish
Pages (from-to)3564-3572
Number of pages9
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume48
Issue number16
DOIs
Publication statusPublished - 2010 Aug 15
Externally publishedYes

Keywords

  • ε-caprolactone
  • Catalysts
  • Magnesium
  • Polycarbonates
  • Polyesters
  • Ring-opening polymerization
  • Sulfonate phenoxide
  • Trimethylene carbonate

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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