Novel Naphthalene-Based Crown Ether: Synthsis, Crystal Structure and Its Complexation with Paraquat Derivatives

A Novel naphthalene-based crown ether has been synthesized by the etherification of 2,7-dihydroxynaphthalene with 8-tosyloxy-3,6-dioxaoctanol in the presence of K2CO3, followed by reaction with p-toluenesufonyl chloride to give 7. Compound 7 was further reacted with 2,7-dihydroxynaphthalene in the presence of cesium carbonate to give 1 in 38% total yield. Its crystal structure was determined by X-ray diffraction method. The crystal is of triclinic, space group P-1 with a= 8.165(3) angstrom, b=13.435(4) angstrom, c= 14.083(3) angstrom, alpha=64.11(2)degrees, beta=80.40(3)degrees, gamma=88.19(3)degrees, V=1368.9(7) angstrom(3), Z=2, D-c=1.331 g/cm(3), lambda=0.071070 nm, mu(Mo K alpha)=1.331 mm(-1), M-r =353.22, F(000)=584. The crystal structure of 1 shows that two napthalene units are linked two tri(ethylene glycol) bridges to form dinapthalzo[30]crown-8 cavity and one Z-like central cavity with size of ca. 8.2 angstrom x 12.0 angstrom. The host 4 was proved to be a efficient host for the complexation with paraquat derivatives in solution by H-1 NMR.