Synthesis and preliminary study of a cryptand designed to allow potassium ion displacement of a fluorescence quencher

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Yao, Min
Sousa, Lynn R.
Issue Date
Thesis (M.S.)
Department of Chemistry
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A new cryptand, 1,18-bis[(phenylmethoxy)methyl]-3,16,20,23,26,29,32,35-octaoxatetracyclo-[16.9.9,05,10 09,14]hexatriaconta-5,7,9,11,13-pentaene was synthesized from cis-9,19-bis(benzyloxymethyl)-1,4,7,11,14,17-hexaoxacycloeicosane-9,l9-diyldimethanol and l,5-bis(bromomethyl)naphthlene in the presence of t-butoxide base. The overall syntheses involved five steps. The new cryptand compound has a melting point at 164-1650 C, and the yield was 18.5%. The NMR spectra and the crystal structure determination proved the synthesized cryptand the same as that desinged.Fluorescent measurements were performed with this cryptand. The fluorescence was found to be quenched by cesium ion, and the quenching increased with the increasing of cesium ion concentration. The average quenching of the fully complexed (with Cs +) cryptand was estimated as 20 + 2% by a computerized data fitting program. The complexation constant was determined to be 16 ± 5 M-1. A possible explanation for these observations is presented.