Abstract: | A novel chiral calix4](azoxa)crown-7 (9) has been synthesized and its metal ion recognition properties investigated. The starting reagents, chiral diamine 5 and calix4]arene diacid chloride derivative 8, were prepared according to literature methods. 1H and 13C NMR data show that 9 exists in a cone conformation. In liquid–liquid extraction experiments, 9 exhibits selectivity for Li+ among the other alkali metals and a good extraction ability for transition metal cations, suggesting its potential use in different fields, such as a sensor for ions as well as for chiral molecules. |