Faculty Advisor

W.Grant McGimpsey

Abstract

The drawbacks of nonactin, the current commercial standard receptor for ammonium ion necessitate the development of new ammonium ionophores. We have designed and attempted to synthesize fluoroionophores, I- III. Molecular modeling of I suggests superior selectivity over that of nonactin. III was synthesized as a selective ionophore for optical detection of ammonium ion. The synthetic strategies for III are two-fold: solid phase and solution phase. Solution phase synthesis was performed with two different protecting groups (t-butyl ester and benzyl ester). A methyl-amino substituted anthracene molecule will be covalently coupled to the secondary amine group to provide an optical signaling moiety that operates on the basis of an“off-on" fluorescence emission mechanism. Compound IV was also synthesized in order to provide a sample reaction for the covalent coupling of the chromophore and to provide a fast route to an ammonium fluoroionophore.

Publisher

Worcester Polytechnic Institute

Degree Name

MS

Department

Chemistry & Biochemistry

Project Type

Thesis

Date Accepted

2003-05-06

Accessibility

Unrestricted

Subjects

sensor, synthesis, bicyclic, fluoroionophore, nonactin, ion-selective, ammonium, Ionophores, Ammonium ions

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