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Synthesis and characterization of 24‐membered cyclobis(ethylene 2,6‐naphthalate)
Author(s) -
Xie Donghang,
Slebodnick Carla,
Gibson Harry W.
Publication year - 2020
Publication title -
journal of polymer science
Language(s) - English
Resource type - Journals
eISSN - 2642-4169
pISSN - 2642-4150
DOI - 10.1002/pol.20190251
Subject(s) - chemistry , ring (chemistry) , yield (engineering) , ethylene , dimer , pyridine , ring strain , naphthalene , catalysis , polymer chemistry , crystallography , chloride , medicinal chemistry , organic chemistry , materials science , metallurgy
The pure 24‐membered cyclic dimer ( 2 ) of ethylene 2,6‐naphthalate was isolated in 9% yield by reaction of bis(2′‐hydroxyethyl) 2,6‐naphthalate ( 5 ) with 2,6‐naphthalenedicarbonyl chloride ( 4 ) in THF with pyridine as catalyst under high dilution conditions. The macrocycle was characterized by NMR, MS, elemental analysis, and X‐ray crystallography. The crystal structure reveals a significant distortion of the naphthalene rings, forming an ellipsoidal cavity as a result of the ring strain, suggesting facile ring‐opening polymerization.