TBD-Catalyzed Ring-Opening Polymerization of Alkyl-Substituted Morpholine-2,5-Dione Derivatives

被引：30

作者：

Dirauf, Michael ^{[1
,2
]}

Bandelli, Damiano ^{[1
,2
]}

Weber, Christine ^{[1
,2
]}

Goerls, Helmar ^{[3
]}

Gottschaldt, Michael ^{[1
,2
]}

Schubert, Ulrich S. ^{[1
,2
]}

机构：

[1] Friedrich Schiller Univ Jena, Lab Organ & Macromol Chem IOMC, Humboldtstr 10, D-07743 Jena, Germany

[2] Friedrich Schiller Univ Jena, Jena Ctr Soft Matter, Philosophenweg 7, D-07743 Jena, Germany

[3] Friedrich Schiller Univ Jena, Lab Inorgan & Analyt Chem IAAC, Humboldtstr 8, D-07743 Jena, Germany

来源：

MACROMOLECULAR RAPID COMMUNICATIONS | 2018年 / 39卷 / 23期

关键词：

5-diones; amino acids; crystal structure; morpholine-2; poly(ester amide)s; ring-opening polymerization; TRIBLOCK COPOLYMERS; POLYDEPSIPEPTIDES; CHALLENGES; GUANIDINE; CARRIERS;

D O I：

10.1002/marc.201800433

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

In a two-step synthesis, five different alkyl-substituted morpholine-2,5-dione monomers were synthesized from the natural amino acids glycine, alanine, valine, leucine, and isoleucine. The heterocyclic compounds crystallize in a boat-like conformation and are polymerized via 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed ring-opening polymerization (ROP) in tetrahydrofuran. Well-defined polymers could be obtained from the monomers based on valine, leucine, and isoleucine at a feed ratio of M/I/TBD = 100/1/0.5. Kinetic studies of the ROP reveal that the molar masses and dispersities (D < 1.2) could be well controlled, as confirmed by size exclusion chromatography and H-1 NMR spectroscopy. At conversions above 50%, the polymerization rate decreases and the dispersity slightly increases, presumably due to transesterification. Matrix-assisted laser desorption time-of-flight mass spectrometry indicates the presence of polymer chains with alpha-end groups derived from the initiator.

引用

页数：5

共 45 条

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