KOELLER, Sylvain; KADOTA, Joji; DEFFIEUX, Alain; PERUCH, Frédéric; MASSIP, Stéphane; LÉGER, Jean-Michel; DESVERGNE, Jean-Pierre; BIBAL, Brigitte

doi:10.1021/ja906119t

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KOELLER, Sylvain
Institut des Sciences Moléculaires [ISM]

KADOTA, Joji
Laboratoire de Chimie des Polymères Organiques [LCPO]

DEFFIEUX, Alain
Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering

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Journal of the American Chemical Society. 2009, vol. 131, n° 42, p. 15088-15130

American Chemical Society

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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.< Leer menos

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LIVING POLYMERIZATION

DONORS

DERIVATIVES

CATALYSTS

RECOGNITION

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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

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