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An Efficient and General Strategy toward the Synthesis of Polyethylene-Based Cyclic Polymers
journal contribution
posted on 2018-04-13, 00:00 authored by Yu Jiang, Zhen Zhang, De Wang, Nikos HadjichristidisA novel strategy
toward well-defined polyethylene-based cyclic
homo/copolymers is presented. Tris(3-(anthracen-9-ylmethoxy)propyl)borane,
prepared by hydroboration of 9-((allyloxy)methyl)anthracene
with BH3, was used to initiate the polyhomologation of
dimethylsulfoxonium methylide to afford well-defined anthracene-teminated
linear polyethylene (PE). The azido and alkynyl groups at α
and ω positions of the PE chain were introduced via the anthracene/maleimide
Diels–Alder (D–A) reaction and esterification, respectively.
Subsequent intramolecular “click” cyclization of the
α,ω-heterofunctionalized linear PE gave cyclic PE.
Combining this efficient strategy with ring-opening polymerization
(ROP), more complex PE-based cyclic block copolymer architectures
have been designed and synthesized, such as diblock cyclic and triblock
tadpole copolymers. All intermediates and final products were characterized
by high-temperature gel permeation chromatography, proton nuclear
magnetic resonance spectroscopy, and differential scanning calorimetry.
Initial studies on the thermal behavior of the cyclic homo- and block
copolymers revealed the big influence of the cyclic structure on the
melting temperature and crystallinity as compared to their corresponding
precursors.
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novel strategyPE chainInitial studiestriblock tadpole copolymersring-opening polymerizationGeneral StrategyROPgel permeation chromatographyalkynyl groupsscanning calorimetryresonance spectroscopydiblock cyclicPolyethylene-Based Cyclic PolymersBH 3cyclic structurePE-based cyclic block copolymer architecturescyclic PEblock copolymersω positionscyclic homo
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