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Title: Organocatalytic Stereoselective Ring-Opening Polymerization of Lactide with Dimeric Phosphazene Bases

Abstract

Highly isotactic polylactide with a high melting temperature was synthesized from rac-lactide through an organocatalytic route using dimeric phosphazene base 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2 5,4 5-catenadi(phosphazene) (P2-t-Bu) catalyst at low temperature. Microstructural analysis of the prepared polymer using homodecoupled 1H NMR spectroscopy revealed the formation of a stereoblock architecture containing long isotactic sequence of R- and S- blocks in the main chain. A proposed mechanism involving chain-end control and stereoerror explains the stereoselective polymerization.

Authors:
 [1];  [1];  [2];  [1];  [1];  [1]
  1. Almaden Research Center
  2. ORNL
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Center for Nanophase Materials Sciences
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
940792
DOE Contract Number:
DE-AC05-00OR22725
Resource Type:
Journal Article
Resource Relation:
Journal Name: Journal of the American Chemical Society; Journal Volume: 129; Journal Issue: 42
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; CATALYSTS; POLYMERIZATION; LACTATES; ORGANIC PHOSPHORUS COMPOUNDS; ORGANIC POLYMERS; STEREOCHEMISTRY; MOLECULAR STRUCTURE

Citation Formats

Zhang, Lei, Nederberg, Fredrik, Messman, Jamie M, Pratt, Russel C, Hedrick, James, and Wade, Charles G. Organocatalytic Stereoselective Ring-Opening Polymerization of Lactide with Dimeric Phosphazene Bases. United States: N. p., 2007. Web. doi:10.1021/ja074131c.
Zhang, Lei, Nederberg, Fredrik, Messman, Jamie M, Pratt, Russel C, Hedrick, James, & Wade, Charles G. Organocatalytic Stereoselective Ring-Opening Polymerization of Lactide with Dimeric Phosphazene Bases. United States. doi:10.1021/ja074131c.
Zhang, Lei, Nederberg, Fredrik, Messman, Jamie M, Pratt, Russel C, Hedrick, James, and Wade, Charles G. Mon . "Organocatalytic Stereoselective Ring-Opening Polymerization of Lactide with Dimeric Phosphazene Bases". United States. doi:10.1021/ja074131c.
@article{osti_940792,
title = {Organocatalytic Stereoselective Ring-Opening Polymerization of Lactide with Dimeric Phosphazene Bases},
author = {Zhang, Lei and Nederberg, Fredrik and Messman, Jamie M and Pratt, Russel C and Hedrick, James and Wade, Charles G},
abstractNote = {Highly isotactic polylactide with a high melting temperature was synthesized from rac-lactide through an organocatalytic route using dimeric phosphazene base 1-tert-butyl-2,2,4,4,4-pentakis(dimethylamino)-2 5,4 5-catenadi(phosphazene) (P2-t-Bu) catalyst at low temperature. Microstructural analysis of the prepared polymer using homodecoupled 1H NMR spectroscopy revealed the formation of a stereoblock architecture containing long isotactic sequence of R- and S- blocks in the main chain. A proposed mechanism involving chain-end control and stereoerror explains the stereoselective polymerization.},
doi = {10.1021/ja074131c},
journal = {Journal of the American Chemical Society},
number = 42,
volume = 129,
place = {United States},
year = {Mon Jan 01 00:00:00 EST 2007},
month = {Mon Jan 01 00:00:00 EST 2007}
}