Tripartite hydrogen-bonding as a driving force for high-concentration cyclization of poly(l-lactide)
Sébastien Moins, Alexandre Mignot, Céline Henoumont, Sophie Laurent, Philippe Leclère, Olivier Coulembier
TL;DR
A new method uses hydrogen bonding to efficiently create large cyclic polylactide molecules under practical conditions.
Contribution
A tripartite hydrogen-bonding complex enables high-concentration cyclization of poly(l-lactide) with practical synthetic conditions.
Findings
Cyclic PLLA with Mn ≈ 26,000 g mol⁻¹ was achieved at 0.5 M concentration.
Nanorings with diameters matching expected chain lengths were observed via SPM imaging.
Intramolecular transesterification at a benzylic ester triggers ring closure efficiently.
Abstract
A three-step strategy enables efficient cyclization of high-Mn PLLA at 0.5 M. Key to success is a persistent tripartite complex driven by hydrogen bonding and ion pairing. Selective intramolecular transesterification at a benzylic ester triggers ring closure, affording cyclic PLLA (Mn ≈ 26 000 g mol−1) under synthetically practical conditions. SPM imaging reveals nanorings with diameters consistent with the expected contour length of cyclic PLLA chains. A three-step strategy enables efficient cyclization of high-Mn PLLA at 0.5 M.
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Taxonomy
Topicsbiodegradable polymer synthesis and properties · Synthetic Organic Chemistry Methods · Enzyme Catalysis and Immobilization