Stereocontrolled polymerization of racemic lactide with chiral initiator: Combining stereoelection and chiral ligand-exchange mechanism

被引：233

作者：

Majerska, K ^{[1
]}

Duda, A ^{[1
]}

机构：

[1] Polish Acad Sci, Dept Polymer Chem, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 04期

关键词：

D O I：

10.1021/ja0388966

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New opportunities, provided by the 2,2′-[1,1′-binaphthyl-2,2′-diylbis(nitrylomethilidyne)]diphenol (SB(OH)2)/Al(OiPr)3/racemic lactide (rac-LA) polymerization system, employing a combination of stereoelection with (S) and (R) ligand-exchange mechanism at Al-alkoxide active centers were explored. The stereoelectivity was comparable to that determined for the process with an additional synthetic step of isolation and purification of the SBO2Al-OiPr alkoxide. The resultant poly(rac-LA) had a gradient stereocopolymer structure and exhibited enhanced thermal stability due to a stereocomplex formation (Tm = 210 °C). This is the highest melting temperature reported until now for poly(lactide) (PLA) prepared directly from rac-LA. Copyright © 2004 American Chemical Society.

引用

页码：1026 / 1027

页数：2

共 26 条

[1] Metalloporphyrins as initiators for living and immortal polymerizations [J].

Aida, T ;

Inoue, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (01) :39-48

[2]

[Anonymous], AM CHEM S SER

[3] Polymerization of lactide by monomeric Sn(II) alkoxide complexes [J].

Aubrecht, KB ;

Hillmyer, MA ;

Tolman, WB .

MACROMOLECULES, 2002, 35 (03) :644-650

[4] Polymerization of lactide with zinc and magnesium β-diiminate complexes:: Stereocontrol and mechanism [J].

Chamberlain, BM ;

Cheng, M ;

Moore, DR ;

Ovitt, TM ;

Lobkovsky, EB ;

Coates, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (14) :3229-3238

[5] Single-site catalysts for ring-opening polymerization:: Synthesis of heterotactic poly(lactic acid) from rac-lactide [J].

Cheng, M ;

Attygalle, AB ;

Lobkovsky, EB ;

Coates, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (49) :11583-11584

[6] Monodisperse enantiomeric lactic acid oligomers: Preparation, characterization, and stereocomplex formation [J].

de Jong, SJ ;

van Dijk-Wolthuis, WNE ;

Kettenes-van den Bosch, JJ ;

Schuyl, PJW ;

Hennink, WE .

MACROMOLECULES, 1998, 31 (19) :6397-6402

[7] POLYMERIZATION OF EPSILON-CAPROLACTONE INITIATED BY ALUMINUM ISOPROPOXIDE TRIMER AND/OR TETRAMER [J].

DUDA, A ;

PENCZEK, S .

MACROMOLECULES, 1995, 28 (18) :5981-5992

[8]

DUDA A, 2002, BIOPOLYMERS B, V3, P371

[9] Polymerization of L,L-lactide initiated by aluminum isopropoxide trimer or tetramer [J].

Kowalski, A ;

Duda, A ;

Penczek, S .

MACROMOLECULES, 1998, 31 (07) :2114-2122

[10] RING-OPENING OLIGOMERIZATION REACTIONS USING ALUMINUM COMPLEXES OF SCHIFF-BASES AS INITIATORS [J].

LEBORGNE, A ;

VINCENS, V ;

JOUGLARD, M ;

SPASSKY, N .

MAKROMOLEKULARE CHEMIE-MACROMOLECULAR SYMPOSIA, 1993, 73 :37-46

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