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Improved and Controlled Complexation of Paraquat Derivatives by the Formation of a Bis( m ‐phenylene)‐26‐Crown‐8‐Based Lariat Ether
Author(s) -
Zhang Mingming,
Luo Yan,
Zheng Bo,
Xia Binyuan,
Huang Feihe
Publication year - 2010
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.201000926
Subject(s) - paraquat , chemistry , crown ether , ether , phenylene , polymer chemistry , solid state , medicinal chemistry , stereochemistry , organic chemistry , ion , polymer
A novel bis( m ‐phenylene)‐26‐crown‐8‐based lariat ether (i.e., 3b ) was synthesized and characterized. It can bind paraquat derivatives more strongly than bis( m ‐phenylene)‐26‐crown‐8 in solution. It forms pseudorotaxanes with two paraquat derivatives in the solid state. N ‐Methyl substitution was found to play an important role on the binding strength of lariat ether 3b . Furthermore, due to the introduction of two benzyloxy groups, its binding to paraquat derivatives can be switched off (and back on) by adding K + (and then dibenzo‐18‐crown‐6), and the disassociation percentage depends on the concentration of the added K + ions.