Synthesis And Properties Research Of Calix[4]azacrown Derivatives Containing Fluorescent Groups

The synthesis of fluorescent sensors, which can selectively recognize and sensing heavy and transition metal ions through color or fluorescence changes, has received increasing interest in supramolecular chemistry. Calix[4]azacrown deriatives are good candidates as receptors of fluorescent probe molecules, due to their binding strength and selectivity toward soft-metal ions through the three-dimensional encapsulating assistance of the appended side arm on the nitrogen atom. In this paper, we report several novel series of calix[4]azacrown detivatives with phthalimide and naphthalimide groups, one of which can selectively recognize Cu2+ and the color change is visible and may be useful fluorescent sensor.By using three multi-oxyethyl p-methylbenzenesulfonate compounds, three novel derivatives of calix[4]azacrown connecting with the nitrogen atom have been synthesized and structurally characterized by 1H NMR,13C NMR,IR and MS. And all the three compounds adopt cone conformation. Due to different length of the chains, A novel ?tren'type calix[4]azacrown ether and a novel ?spiro'type calix[4]azacrown containing morpholine unit and a expected [2]pseudorotaxane was prepared.With introducing four phthalimide compounds into calix[4]arene on the low rim after ipso-nitration, reduction, bromo-acetamidation and substitution, we have successfully obtained four new compounds including three new intermediates. All these compouds are confirmed by 1H NMR,13C NMR,IR and MS and the data means that all of them adopt the cone conformation.By the reaction of phthalimide compounds and calix[4]azacrown, two series, six new calix[4]azacrown derivatives were prepared. Then with introducing naphthalimide compounds into calix[4]azacrown, four novel derivatives of calix[4]azacrown connecting with the nitrogen atom have been synthesized and structurally characterized by 1H NMR,13C NMR,IR and MS. And all the ten compounds adopt cone conformation. After fluorescent properties research of metal ions, the results showed that one of which can selectively recognize Cu2+ ,the color change is visible and may be a useful fluorescent sensor.