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Efficient Syntheses and Complexation Studies of Diacetylene‐Containing Macrocyclic Polyethers
Author(s) -
Feng Yahui,
Li Jingning,
Jiang Lasheng,
Gao Zhihong,
Huang Weicong,
Jiang Fei,
Luo Nianhua,
Han Shujuan,
Zeng Ronghua,
Yang Dingqiao
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001140
Subject(s) - chemistry , diacetylene , triethylene glycol , polymer chemistry , pyridinium , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , polymerization , polymer
Abstract A series of novel macrocyclic polyethers, phenylene–diacetylene‐containing macrocycles was synthesized in high yields by employing copper(II)‐mediated Eglinton coupling as the key macrocyclization (80–92 %). As an analogue of the bisphenylene crown ether hosts, the binding behavior of these new macrocycles was investigated by 1 H NMR spectroscopy, mass spectrometry (ESI), and X‐ray crystallography. The results obtained indicate that macrocycles with tetraethylene glycol chains ( 3c – e ) bind a paraquat guest to form [2]pseudorotaxane‐like complexes in solution and in the solid state, whereas macrocycles with triethylene glycol chains (i.e., 3f – h ) bind a paraquat guest to form [3]pseudorotaxane‐like complexes, which implies that macrocycles 3f – h may be able to complex to (mono)pyridinium cations in a [2]pseudorotaxane‐like fashion in solution.