Ring-Opening Polymerization of L-Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between L-Lactide and the Hydrogen-Bonding Organocatalyst - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2009

Ring-Opening Polymerization of L-Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between L-Lactide and the Hydrogen-Bonding Organocatalyst

Résumé

N-(3,5-Bis(trifluoromethyl)phenyl)-1H-indole-2-carboxamide le is an efficient hydrogen-bonding organocatalyst for the ring-opening polymerization Of L-lactide. This new catalytic species does control the dispersity (1.08) and molecular weight (3460 g/mol vs 3064 in theory) of the poly(L-lactides) prepared in 2 h. H-1 NMR analysis showed that compound le complexes L-lactide in CDCl3 through the two available NH groups (amide and indole). In particular, the catalytic species appeared to be mainly the H-bonding donor amide (le in extended conformation, alone or dimer (1e)(2)) and, to a Lesser extend, the dual H-bonding amido-indole (1e in its the pinched conformation). The first X-ray structure of the complex between a H-bonding organocatalyst and L-lactide also revealed a tight H-bonded network between the dimer (1e)(2) and L-lactide.

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hal-00503817 , version 1 (19-07-2010)

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Sylvain Koeller, Joji Kadota, Alain Deffieux, Frédéric Peruch, Stéphane Massip, et al.. Ring-Opening Polymerization of L-Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between L-Lactide and the Hydrogen-Bonding Organocatalyst. Journal of the American Chemical Society, 2009, 131 (42), pp.15088-15130. ⟨10.1021/ja906119t⟩. ⟨hal-00503817⟩
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