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Redox Switchable Ionophores for Heavy and Transition Metal Cations
Author(s) -
Hennrich Gunther,
Sonnenschein Helmut,
ReschGenger Ute
Publication year - 2000
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/(sici)1099-0690(200002)2000:3<539::aid-ejoc539>3.0.co;2-b
Subject(s) - chemistry , redox , substituent , ether , transition metal , polymer chemistry , metal , combinatorial chemistry , polyethylene glycol , crown ether , inorganic chemistry , medicinal chemistry , organic chemistry , catalysis , ion
First examples of new, modular, redox switchable ionophores for heavy and transition metal cations are presented. These systems are based on a crown ether or polyethylene glycol unit substituted by the 1,2,4‐thiadiazole/iminoylthiourea redox system ( 2a‐4a , 2b‐4b ). The syntheses via a Boulton‐Katritzki rearrangement are described and their cation selectivities, studied by extraction experiments, proved to be determined by the systems' redox state. Additionally, simple 5‐anilino‐3‐phenyl‐1,2,4‐thiadiazole ( 5a ) and the corre‐sponding iminoylthiourea ( 5b ), which do not contain a potential cation binding polyether substituent were also tested to investigate the complexation property of the redox active building block itself.