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Synthesis of a Bis(1,2,3‐phenylene) Cryptand and Its Dual‐Response Binding to Paraquat and Diquat
Author(s) -
Zhang Mingming,
Zheng Bo,
Xia Binyuan,
Zhu Kelong,
Wu Chuande,
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.201001034
Subject(s) - diquat , paraquat , cryptand , chemistry , medicinal chemistry , phenylene , stereochemistry , polymer chemistry , organic chemistry , ion , polymer
A bis(1,2,3‐phenylene) cryptand has been synthesized and used to prepare 1:1 complexes with paraquat and diquat, with association constants of 2.2 × 10 3 M –1 and 3.7 × 10 3 M –1 , respectively, in CHCl 3 /CH 3 CN (1:1). In the solid state this cryptand forms a taco complex with paraquat, which has never been found before in cryptand/paraquat complexes. Furthermore, its binding to paraquat and diquat in solution can be switched off (and back on) by addition of acid or K + (and then base or 18‐crown‐6).