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Synthesis of Well-Defined Dihydroxy Telechelics by (Co)polymerization of Morpholine-2,5-Diones Catalyzed by Sn(IV) Alkoxide

  • Well-defined dihydroxy telechelic oligodepsipeptides (oDPs), which have a high application potential as building blocks for scaffold materials for tissue engineering applications or particulate carrier systems for drug delivery applications are synthesized by ring-opening polymerization (ROP) of morpholine-2,5-diones (MDs) catalyzed by 1,1,6,6-tetra-n-butyl-1,6-distanna-2,5,7,10-tetraoxacyclodecane (Sn(IV) alkoxide). In contrast to ROP catalyzed by Sn(Oct)(2), the usage of Sn(IV) alkoxide leads to oDPs, with less side products and well-defined end groups, which is crucial for potential pharmaceutical applications. A slightly faster reaction of the ROP catalyzed by Sn(IV) alkoxide compared to the ROP initiated by Sn(Oct)(2)/EG is found. Copolymerization of different MDs resulted in amorphous copolymers with T(g)s between 44 and 54 degrees C depending on the molar comonomer ratios in the range from 25% to 75%. Based on the well-defined telechelic character of the Sn(IV) alkoxide synthesized oDPs as determined by matrix-assisted laserWell-defined dihydroxy telechelic oligodepsipeptides (oDPs), which have a high application potential as building blocks for scaffold materials for tissue engineering applications or particulate carrier systems for drug delivery applications are synthesized by ring-opening polymerization (ROP) of morpholine-2,5-diones (MDs) catalyzed by 1,1,6,6-tetra-n-butyl-1,6-distanna-2,5,7,10-tetraoxacyclodecane (Sn(IV) alkoxide). In contrast to ROP catalyzed by Sn(Oct)(2), the usage of Sn(IV) alkoxide leads to oDPs, with less side products and well-defined end groups, which is crucial for potential pharmaceutical applications. A slightly faster reaction of the ROP catalyzed by Sn(IV) alkoxide compared to the ROP initiated by Sn(Oct)(2)/EG is found. Copolymerization of different MDs resulted in amorphous copolymers with T(g)s between 44 and 54 degrees C depending on the molar comonomer ratios in the range from 25% to 75%. Based on the well-defined telechelic character of the Sn(IV) alkoxide synthesized oDPs as determined by matrix-assisted laser desorption/ionization time of flight measurements, they resemble interesting building blocks for subsequent postfunctionalization or multifunctional materials based on multiblock copolymer systems whereas the amorphous oDP-based copolymers are interesting building blocks for matrices of drug delivery systems.show moreshow less

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Author details:Xingzhou PengORCiDGND, Marc BehlORCiDGND, Pengfei Zhang, Magdalena Mazurek-BudzynskaORCiD, Yakai FengORCiDGND, Andreas LendleinORCiDGND
DOI:https://doi.org/10.1002/mabi.201800257
ISSN:1616-5187
ISSN:1616-5195
Pubmed ID:https://pubmed.ncbi.nlm.nih.gov/30318738
Title of parent work (English):Macromolecular bioscience
Publisher:Wiley-VCH
Place of publishing:Weinheim
Publication type:Article
Language:English
Date of first publication:2018/10/14
Publication year:2018
Release date:2021/06/22
Tag:Sn(IV) alkoxide; oligodepsipeptides; ring-opening polymerization; telechelics; tin(II) 2-ethylhexanoate
Volume:18
Issue:12
Number of pages:11
Funding institution:Helmholtz AssociationHelmholtz Association; Tianjin University-Helmholtz-Zentrum Geesthacht Joint Laboratory for Biomaterials and Regenerative Medicine - German Federal Ministry of Education and Research (BMBF) [0315496]; Chinese Ministry of Science and Technology (MOST)Ministry of Science and Technology, China [2013DFG52040]; Deutsche Forschungsgemeinschaft (DFG) through the Collaborative Research Centre 1112 "Nanocarriers"; China Scholarship Council (CSC)China Scholarship Council [201206250098]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Peer review:Referiert
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