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Calix[4] crowns with Methoxynaphthoylmethyl Pendant Groups
Author(s) -
Jin ChuanMin,
Lu GuoYuan,
Zhang ChaoZhi,
Shi ZhengWei,
You XiaoZeng
Publication year - 2003
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20030211103
Subject(s) - chemistry , picrate , calixarene , selectivity , titration , fluorescence , crown ether , ether , alkylation , proton nmr , polymer chemistry , medicinal chemistry , extraction (chemistry) , stereochemistry , inorganic chemistry , organic chemistry , ion , molecule , physics , quantum mechanics , catalysis
Abstract The novel calix [4] crowns with two pendant groups were prepared by the alkylation of calix [4] crowns with 6‐methoxy‐2‐bromoacetylnaphthalene. 1 H NMR titration and picrate extraction experiments indicated that they exhibit higher complexing efficiency than their parent compounds and possess obvious selectivity for Na + or K + , respectively, and that the cation is encapsulated inside the preorganized ionophoric cavity defined by carbonyl oxygens, the crown ether and the phenoxy oxygens. From UV and fluorescent spectra it is revealed that calix [4]‐crown‐4 3a with 6‐methoxy‐2‐naphthoylmethyl pedant groups exhibits remarkable cation‐induced photophysical effects and it could be utilized as a selective fluorescent sensor for Ca 2+ .