Volume 2019, Issue 22 p. 2768-2773
Full Paper

Salalens and Salans Derived from 3-Aminopyrrolidine: Aluminium Complexation and Lactide Polymerisation

Luke Britton

Luke Britton

Department of Chemistry, University of Bath, BA2 7AY UK Bath

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Daniel Ditz

Daniel Ditz

Department of Chemistry, University of Bath, BA2 7AY UK Bath

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James Beament

James Beament

Department of Chemistry, University of Bath, BA2 7AY UK Bath

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Paul McKeown

Corresponding Author

Paul McKeown

Department of Chemistry, University of Bath, BA2 7AY UK Bath

Department of Chemistry, University of Bath, Bath BA2 7AY UK

E-mail: [email protected]

E-mail: [email protected]

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Helena C. Quilter

Helena C. Quilter

Department of Chemistry, University of Bath, BA2 7AY UK Bath

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Kerry Riley

Kerry Riley

Department of Chemistry, University of Bath, BA2 7AY UK Bath

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Mary F. Mahon

Mary F. Mahon

Department of Chemistry, University of Bath, BA2 7AY UK Bath

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Matthew D. Jones

Corresponding Author

Matthew D. Jones

Department of Chemistry, University of Bath, BA2 7AY UK Bath

Department of Chemistry, University of Bath, Bath BA2 7AY UK

E-mail: [email protected]

E-mail: [email protected]

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First published: 13 May 2019
Citations: 5

Graphical Abstract

A series of AlIII complexes with salan and salalen ligands were prepared. These were trialled for the controlled ROP of rac-LA. The salan complexes were shown to be significantly more active for the polymerisation.

Abstract

In this paper a series of 7 salalen ligands based on an aminopyrrolidine backbone have been prepared and characterised. Several systems have been reduced to the salan ONNO type-ligand. All ligands have been complexed to AlIII with Al(1–7)Me, Al(2a)(OiPr) and Al(7a)Me being characterised by single-crystal X-ray diffraction. In general the AlIII centres are best described as being in a trigonal bipyramidal geometry. The solution and solid-state structures are discussed. All complexes have all been trialled for the production of PLA from rac-lactide, the salalen complexes had a preference for heterotactic PLA (Pr = 0.71), whereas the salan had a more isotactic bias (Pm = 0.72). In all cases PLA with low dispersities and predictable molecular weights were prepared. The activity of the two classes of ligands is compared with the salan complexes appearing to be significantly more active than the salalen systems.