Jozef Hodyl PhD Thesis - Theses - Flinders University

The model receptor ligand 51 was prepared by heating a stirred acetonitrilesolution of 46 with a 100% excess of (S)-(-)-propylene oxide, 75, and lithiumbromide, in a sealed pressure vessel at 80 o C for 72 hours, Scheme 2.9.Scheme 2.9 Synthesis of the silica attached molecular receptor model precursor, 51.Following the reaction, the desired product, 51, was extracted with chloroform,after the addition of water to the reaction mixture to remove the lithium bromide.The resulting extract was concentrated in vacuo to give 51 in 97% yield and highpurity. Analysis of the 13 C and 13 C APT spectra of compound 51 revealed theappearance of three distinct peaks for the methyl, methylene and methine carbons ofthe appended hydroxypropyl pendant arm. The chemical shifts of the resonances dueto the three phenoxy and the hydroxypropyl pendant arms were at positions normally94, 174found for these moieties.2.7 Metal ion complexation with the silica attached receptormodel2.7.1 Molecular receptors activated by metal ion coordination: BackgroundPrevious studies of cyclen based receptor complexes have demonstrated that upon49