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Synthesis of Well‐Defined Dihydroxy Telechelics by (Co)polymerization of Morpholine‐2,5‐Diones Catalyzed by Sn(IV) Alkoxide
Author(s) -
Peng Xingzhou,
Behl Marc,
Zhang Pengfei,
MazurekBudzyńska Magdalena,
Feng Yakai,
Lendlein Andreas
Publication year - 2018
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.201800257
Subject(s) - alkoxide , copolymer , polymerization , comonomer , polymer chemistry , chemistry , catalysis , amorphous solid , materials science , organic chemistry , polymer
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 °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.