Ambient temperature catalyst-free light-induced preparation of macrocyclic aliphatic polyesters

被引：33

作者：

Josse, Thomas ^{[1
,2
]}

Altintas, Ozcan ^{[3
,4
]}

Oehlenschlaeger, Kim K. ^{[3
,4
]}

Dubois, Philippe ^{[1
]}

Gerbaux, Pascal ^{[2
]}

Coulembier, Olivier ^{[1
]}

Barner-Kowollik, Christopher ^{[3
,4
]}

机构：

[1] Univ Mons, Ctr Innovat & Res Mat & Polymers CIRMAP, Lab Polymer & Composite Mat, B-7000 Mons, Belgium

[2] Univ Mons, Interdisciplinary Ctr Mass Spectrometry CISMa, Organ Synth & Mass Spectrometry Lab, B-7000 Mons, Belgium

[3] KIT, Inst Tech Chem & Polymerchem, D-76128 Karlsruhe, Germany

[4] KIT, IBG, D-76344 Eggenstein Leopoldshafen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 16期

关键词：

RING-OPENING POLYMERIZATION; ZWITTERIONIC POLYMERIZATION; CLICK CYCLIZATION; POLYMERS; ORGANOCATALYSTS; LACTONES; LACTIDE;

D O I：

10.1039/c3cc49067j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The light induced, catalyst-free ambient temperature preparation of macrocyclic aliphatic polyesters is pioneered. Based on the photo-induced Diels-Alder reaction of orthoquinodimethane and acrylate moieties, cyclic polyesters of high purity are readily synthesized. Considering the high tolerance to functional groups and the orthogonality of the ligation, the reported protocol can be easily transferred to a large range of polymers, complex topologies (tadpole, sun-shaped, jellyfish, etc.) and applications.

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收藏

页码：2024 / 2026

页数：3

相关论文

共 25 条

[1] Recent developments in ring opening polymerization of lactones for biomedical applications [J].

Albertsson, AC ;

Varma, IK .

BIOMACROMOLECULES, 2003, 4 (06) :1466-1486

[2] A Mild and Efficient Approach to Functional Single-Chain Polymeric Nanoparticles via Photoinduced Diels-Alder Ligation [J].

Altintas, Ozcan ;

Willenbacher, Johannes ;

Wuest, Kilian N. R. ;

Oehlenschlaeger, Kim K. ;

Krolla-Sidenstein, Peter ;

Gliemann, Hartmut ;

Barner-Kowollik, Christopher .

MACROMOLECULES, 2013, 46 (20) :8092-8101

[3] The influence of polymer topology on pharmacokinetics: Differences between cyclic and linear PEGylated poly(acrylic acid) comb polymers [J].

Chen, Bo ;

Jerger, Katherine ;

Frechet, Jean M. J. ;

Szoka, Francis C., Jr. .

JOURNAL OF CONTROLLED RELEASE, 2009, 140 (03) :203-209

[4] POLYPROPYLENE-GRAFT-POLYCAPROLACTONE - SYNTHESIS AND APPLICATIONS IN POLYMER BLENDS [J].

CHUNG, TC ;

RHUBRIGHT, D .

MACROMOLECULES, 1994, 27 (06) :1313-1319

[5] EQUILIBRIUM RING CONCENTRATIONS AND STATISTICAL CONFORMATIONS OF POLYMER-CHAINS .11. CYCLICS IN POLY(ETHYLENE TEREPHTHALATE) [J].

COOPER, DR ;

SEMLYEN, JA .

POLYMER, 1973, 14 (05) :185-192

[6] Single-component catalyst/initiators for the organocatalytic ring-opening polymerization of lactide [J].

Csihony, S ;

Culkin, DA ;

Sentman, AC ;

Dove, AP ;

Waymouth, RM ;

Hedrick, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9079-9084

[7] Zwitterionic polymerization of lactide to cyclic poly(lactide) by using N-heterocyclic carbene organocatalysts [J].

Culkin, Darcy A. ;

Jeong, Wonhee ;

Csihony, Szilard ;

Gomez, Enrique D. ;

Balsara, Nitash R. ;

Hedrick, James L. ;

Waymouth, Robert M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (15) :2627-2630

[8] SYNTHESIS AND INVESTIGATION OF MACROCYCLIC POLYSTYRENE [J].

GEISER, D ;

HOCKER, H .

MACROMOLECULES, 1980, 13 (03) :653-656

[9] Ambient Temperature Synthesis of Triblock Copolymers via Orthogonal Photochemically and Thermally Induced Modular Conjugation [J].

Glassner, Mathias ;

Oehlenschlaeger, Kim K. ;

Gruendling, Till ;

Barner-Kowollik, Christopher .

MACROMOLECULES, 2011, 44 (12) :4681-4689

[10] Synthesis and Degradation Behavior of Cyclic Poly(ε-caprolactone) [J].

Hoskins, Jessica N. ;

Grayson, Scott M. .

MACROMOLECULES, 2009, 42 (17) :6406-6413