Highly stereoelective polymerization of rac‐(D,L)‐lactide with a chiral schiff's base/aluminium alkoxide initiator
Abstract
A chiral Schiff's base/aluminium alkoxide initiator bearing a ligand derived from R‐(+)‐1,1′‐binaphthyl‐2,2′‐diamine was synthesized and used for the stereoelective polymerization of rac‐(D,L)‐lactide. Rather high stereoelectivity is observed: a polymer with 88% enantiomeric enrichment in D units is obtained at 19% conversion. At high conversions a stereocomplex between D‐ and L‐enriched stereocopolymers is formed. The polymerization reaction shows living type features, and narrow molecular weight distributions (M̄w/M̄n = 1,05–1,30) are obtained up to very high conversions. This indicates that transesterification reactions do not occur significantly with this sterically hindered initiator.
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Aluminum complexes supported by SALEN-type ligands are some of the most stereoselective catalysts for the ROP of racemic LA, but their low reactivities limit their applicability.
“Aluminum complexes supported by SALEN-type ligands [301][302][303][304][305][306][307][308][309] are some of the most stereoselective catalysts for the ROP of racemic LA but their low reactivities (typical reaction conditions: Al loading >1 mol%, 70-130 °C, and long reaction time) limit their applicability.”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [301]
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- Authors
- Spassky, N., Wisniewski, M., Pluta, C., & Le Borgne, A.
- Affiliations
- Université Pierre-et-Marie-Curie (FR)
- Corresponding author
- Spassky, Nicolas
- Venue
- Macromolecular Chemistry and Physics
- Publisher
- Wiley
- Published
- 1996-09
- Volume
- 197
- Issue
- 9
- Pages
- 2627-2637
- ISSN
- 1022-1352 (ISSN-L)
- 1521-3935
- OpenAlex
- W2061088416
- Cited by
- 627
- References
- 24
- Citations by year
- 2026: 7 · 2025: 16 · 2024: 29 · 2023: 19 · 2022: 17 · 2021: 22 · 2020: 29 · 2019: 32 · 2018: 21 · 2017: 41 · 2016: 31 · 2015: 36 · 2014: 46 · 2013: 34 · 2012: 26
- FWCI
- 4.77
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Macromolecular Chemistry and Physics (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Chemistry › Organic Chemistry › Asymmetric Synthesis and Catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- BINAM, stereocomplex, living polymerization, enantiomeric enrichment, transesterification, molecular weight distribution
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