ADMET Polymerization of Amino-Acid-Based Diene

被引：19

作者：

Fuehrer, Felix N. ^{[1
]}

Schlaad, Helmut ^{[1
]}

机构：

[1] Max Planck Inst Colloids & Interfaces, Dept Colloid Chem, Potsdam, Germany

来源：

MACROMOLECULAR CHEMISTRY AND PHYSICS | 2014年 / 215卷 / 22期

关键词：

acyclic diene metathesis (ADMET) polymerization; amino acids; diketopiperazine; metathesis; step-growth polymerization; METATHESIS POLYMERIZATION; COPOLYMERS; POLYCONDENSATION; CHEMISTRY; POLYMERS;

D O I：

10.1002/macp.201400166

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

1,4-Di(homo)allyl-2,5-diketopiperazines are synthesized and polymerized via ADMET using the Hoveyda-Grubbs 2nd generation catalyst. The but-3-enylated diketopiperazine can be converted into unsaturated tertiary polyamide with molar mass of <3000 g mol(-1), whereas the allylated diketopiperazine cannot. Double-bond isomerization occurs regardless of whether or not benzoquinone is present. A polyesteramide with a higher molar mass of ca. 4800 g mol(-1) is obtained by the alternating copolymerization (ALTMET) of 1,4-di(but-3-enyl)-2,5-di ketopiperazine and ethylene glycol diacrylate. A post-polymerization modification of the poly(ester)amides via radical thiol-ene chemistry, however, fails.

引用

页码：2268 / 2273

页数：6

共 23 条

[1] ADMET: The Future Revealed [J].

Atallah, Pascale ;

Wagener, Kenneth B. ;

Schulz, Michael D. .

MACROMOLECULES, 2013, 46 (12) :4735-4741

[2] Recent advances in ADMET polymerization [J].

Baughman, TW ;

Wagener, KB .

METATHESIS POLYMERIZATION, 2005, 176 :1-42

[3] Living ring-opening metathesis polymerization [J].

Bielawski, Christopher W. ;

Grubbs, Robert H. .

PROGRESS IN POLYMER SCIENCE, 2007, 32 (01) :1-29

[4] 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products [J].

Borthwick, Alan D. .

CHEMICAL REVIEWS, 2012, 112 (07) :3641-3716

[5]

Choi TL, 2002, ANGEW CHEM INT EDIT, V41, P3839, DOI 10.1002/1521-3773(20021018)41:20<3839::AID-ANIE3839>3.0.CO

[6]

2-H

[7] Alternating diene metathesis polycondensation (ALTMET) - A versatile tool for the preparation of perfectly alternating AB copolymers [J].

Demel, S ;

Slugovc, C ;

Stelzer, F ;

Fodor-Csorba, K ;

Galli, G .

MACROMOLECULAR RAPID COMMUNICATIONS, 2003, 24 (10) :636-641

[8] Improving the selectivity for the synthesis of two renewable platform chemicals via olefin metathesis [J].

Djigoue, Guy Bertrand ;

Meier, Michael A. R. .

APPLIED CATALYSIS A-GENERAL, 2009, 368 (1-2) :158-162

[9] Postfunctionalization of polyoxanorbornene via sequential Michael addition and radical thiol-ene click reactions [J].

Durmaz, Hakan ;

Butun, Muge ;

Hizal, Gurkan ;

Tunca, Umit .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2012, 50 (15) :3116-3125

[10] Synthesis of dipeptide isosteres by cross-metathesis [J].

Enholm, J. Eric ;

Low, Tammy ;

Cooper, Daniel ;

Ghivirija, Ion .

TETRAHEDRON, 2012, 68 (34) :6920-6927

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