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

Abstract

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 K 2 CO 3 , 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) Å, b＝13.435(4) Å, c＝14.083(3) Å, α＝64.11(2)°, β＝80.40(3)°, γ＝88.19(3)°, V＝1368.9(7) Å 3 , Z＝2, D c ＝1.331 g/cm 3 , λ＝0.071070 nm, μ(Mo Kα)＝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 Å×12.0 Å. The host 4 was proved to be a efficient host for the complexation with paraquat derivatives in solution by 1 H NMR.