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Ring-Opening Polymerization of Lactides Catalyzed by Natural Amino-Acid Based Zinc Catalysts

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Department of Chemistry, Texas A&M University, College Station, Texas 77843
*To whom correspondence should be addressed. E-mail: [email protected]. Fax (979)845-0158.
Cite this: Inorg. Chem. 2010, 49, 5, 2360–2371
Publication Date (Web):February 1, 2010
Copyright © 2010 American Chemical Society

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    A series of chiral NNO-tridentate Schiff base ligands derived from natural amino acids were reacted with zinc(bis-trimethylsilylamide)2 to provide metal complexes which have been fully characterized. One of these derivatives was further reacted with p-fluorophenol to yield a phenoxide complex. X-ray crystallographic studies reveal the zinc Schiff base amide complexes to be monomeric, whereas, the p-fluorophenolate complex was shown to be dimeric with bridging phenoxide ligands. All zinc complexes were shown to be very effective catalysts for the ring-opening polymerization (ROP) of lactides at ambient temperature, producing polymers with controlled and narrow molecular weight distributions. These enantiomerically pure zinc complexes did not show selectivity toward either l- or d-lactide, that is, kd(obsd)/kl(obsd) ≈ 1. However, steric substituents on the Schiff base ligands exhibited moderate to excellent stereocontrol for the ROP of rac-lactide. Heterotactic polylactides were produced from rac-lactide with Pr values ranging from 0.68 to 0.89, depending on the catalyst employed and the reaction temperature. The reactivities of the various catalysts were greatly affected by substituents on the Schiff base ligands, with sterically bulky substituents being rate enhancing.

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