Tridentate anilido-aldimine magnesium and zinc complexes as efficient catalysts for ring-opening polymerization of 8-caprolactone and L-Lactide

Yueh Hsuan Tsai, L. I.N. Chia-Her, L. I.N. Chu-Chieh, K. O. Bao-Tsan

Research output: Contribution to journalArticlepeer-review

77 Citations (Scopus)

Abstract

A novel tridentate anilido-aldimine ligand, [o-C6H 4(NHAr)-HC= NCH2CH2NMe2] (Ar = 2,6-iPr2C6H3, L-H, 1), has been prepared by the condensation of N, N-dimethylethylenediamine with one molar equivalent of 2-fluoro-benzaldehyde in hexane, followed by the addition of the lithium salt of diisopropylaniline in THF. Magnesium (Mg) and zinc (Zn) complexes supported by the tridentate anilido-aldimine ligand have been synthesized and structurally characterized. Reaction of L-H (1) with an equivalent amount of MgnBu2 or ZnEt2 produces the monomeric complex [LMgnBu] (2) or [LZnEt] (3), respectively. Experimental results show that complexes 2 and 3 are efficient catalysts for ring-opening polymerization of e-caprolactone (CL) and L-lactide (LA) in the presence of benzyl alcohol and catalyze the polymerization of ε-CL and L-LA in a controlled fashion yielding polymers with a narrow polydispersity index. In both polymerizations, the activity of Mg complex 2 is higher than that of Zn complex 3, which is probably due to the higher Lewis acidity and better oxophilic nature of Mg2+ metal.

Original languageEnglish
Pages (from-to)4927-4936
Number of pages10
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume47
Issue number19
DOIs
Publication statusPublished - 2009 Oct 1
Externally publishedYes

Keywords

  • ε-caprolactone
  • Anilido-aldimine
  • Catalysts
  • L-lactide
  • Magnesium
  • Polyesters
  • Ring-opening polymerization (rop)
  • Tridentate
  • Zinc

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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