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Aminopiperidine based complexes for lactide polymerisation.

P McKeown1, M G Davidson1, J P Lowe2

  • 1Doctoral Training Centre in Sustainable Chemical Technologies, University of Bath, Bath BA2 7AY, UK and Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, UK. mj205@bath.ac.uk.

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Summary
This summary is machine-generated.

New salalen and salan ligands derived from 2-(aminomethyl)piperidine were synthesized and complexed with group 4 metals and aluminum. These complexes showed control over the ring-opening polymerization of rac-lactide, producing both heterotactic and isotactic polylactic acid (PLA).

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Area of Science:

  • Coordination Chemistry
  • Polymer Science
  • Organic Synthesis

Background:

  • Salen and salan ligands are versatile chelating agents.
  • 2-(aminomethyl)piperidine is a useful building block for ligand synthesis.
  • Group 4 metals and aluminum complexes are relevant catalysts in polymerization.

Purpose of the Study:

  • To synthesize novel salalen and salan ligands.
  • To prepare and characterize their metal complexes with group 4 metals and aluminum.
  • To evaluate the catalytic activity of these complexes in the ring-opening polymerization of rac-lactide.

Main Methods:

  • Ligand synthesis via condensation reactions.
  • Metal complexation with Hf, Zr, and Al.
  • Characterization using NMR spectroscopy and X-ray crystallography.
  • Ring-opening polymerization of rac-lactide.

Main Results:

  • Synthesis of bicyclic salan (1-3H2) and imino salalen (4-6H, 7-9H2) ligands.
  • Formation of octahedral group 4 complexes (M(1-3)2) and tetrahedral/trigonal bipyramidal aluminum complexes (Al(1-9)Mex).
  • Demonstration of both heterotactic and isotactic polylactic acid (PLA) formation.
  • Ligand and metal choice influenced polymer tacticity.

Conclusions:

  • The developed ligands and their metal complexes are effective catalysts for controlling PLA tacticity.
  • Group 4 metal complexes favored heterotactic PLA, while aluminum complexes' outcomes were sterically driven.
  • This study provides insights into catalyst design for stereoselective polymerization.