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Development of functional imidazole derivatives: the influence of alkaline metal cations on the rates of CL reactions of 2‐(phenyl and 4‐dimethylaminophenyl)‐4‐hydroperoxy‐4‐3′,4′‐(15‐crown‐5)phenyl‐5‐3″‐4″‐(15‐crown‐5)phenyl‐4 H ‐isoimidazoles
Author(s) -
Kimura Masaru,
Shi Kun,
Hashimoto Koji,
Hu Zhi Zhi
Publication year - 2007
Publication title -
luminescence
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.428
H-Index - 45
eISSN - 1522-7243
pISSN - 1522-7235
DOI - 10.1002/bio.954
Subject(s) - moiety , chemistry , crown ether , denticity , metal , medicinal chemistry , chelation , imidazole , polymer chemistry , photochemistry , stereochemistry , inorganic chemistry , organic chemistry , ion
Abstract Although several investigations have focused on luminescence modulation by chelation with metal cations using bidentate ligands or crown ether systems, a bis(crown ether) system has not yet been used for modulation of chemiluminescence (CL) reactions. In the CL reaction of 2‐(phenyl and 4‐dimethylaminophenyl)‐4‐hydroperoxy‐4‐3′,4′‐(15‐crown‐5)phenyl‐5‐3″,4″(15‐crown‐5)phenyl‐4 H ‐isoimidazoles 2a and b possessing a bis(15‐crown‐5 ether) moiety, the rate acceleration was observed in the presence of K + , Rb + and Cs + due to the holding effect of the bis‐crown moiety, but no rate acceleration was observed by Li + and Na + due to the template effect of the crown moiety. The acceleration of the CL reaction rates is ascribable to the conformational change induced by the scissor‐like motion of the bis‐crown moiety assisted by the holding effect. Copyright © 2007 John Wiley & Sons, Ltd.