Synthesis and study of dibenzodihydroxy-26-crown-8

The objective of this research was to synthesis dibenzo-dihydroxy-26-crown-8 (1) as an ionophore for variety of chemosensors. Complexation of the ionophore (1) to a cation would cause a change of conformation. The conformational changes could affect fluorescence, UV spectra and/or Carbon-13 NMR of the chemosensor, depending on the fluorophores attached to the hydroxyl groups of crown 1 and/ or the identity of the ion. Several synthetic routes for crown 1 formation are given in the proposed synthetic procedure. Bis-1,2[2-hydroxyethoxy]benzene (17), bis-1,2[2-(3-chloro-2-hydroxypropoxy)ethoxy]benzene (18), bis-1,2[2-(2,3-epoxypropoxy)ethoxy]benzene (19) and bis-1,2[2(3-chloro-2-oxopropoxy)ethoxy]benzene (22) were synthesized. The reaction of 17 and 19 was attempted in the presence of SnC14, basic and acidic conditions, and in several solvents. The reaction of 17 and 22, and the reaction of 17 and 1,3-dichloroacetone were attempted in various reaction conditions. Crown 1 may have formed in the reaction of 17 and 19 in methylene chloride/ toluene in the presence of SnCl4 as the Lewis acid.Department of ChemistryThesis (M.S.