Date Presented

Spring 4-2010

Document Type


Degree Name

Bachelor of Science



First Advisor

Dr. Priscilla Gannicott

Second Advisor

Dr. Nancy Cowden

Third Advisor

Dr. David Freier


A receptor with enhanced water solubility was synthesized from an existing receptor to be used as a pyranine fluorescence quencher in endovesiculation detection assays. The existing receptor consisted of a cyclen core with four protruding arms containing an aryl nitro group at each end. Its poor water solubility limited the accuracy and precision of the endovesiculation assay because the low concentration of receptor did not match the concentration of pyranine. To increase the water solubility, ethoxy groups were attached to the ends of each arm by first selectively reducing the nitro group to an amine with NaBHU4, H2, and a Raney nickel slurry, producing a 19% yield. A nucleophilic substitution was then performed to attach a 2-ethoxyethyl group to each amine group. Even though the new receptor’s maximum concentration in water increased, the ability to quench the fluorescence of pyranine decreased dramatically, thus preventing it from being useful in the endovesiculation detection assays.