Worcester Polytechnic Institute Electronic Theses and Dissertations Collection

Title page for ETD etd-0506103-100236


Document Typethesis
Author NameYavuz, Mustafa Selman
URNetd-0506103-100236
TitleSynthesis of an Ammonium Ion-selective Fluoroionophore
DegreeMS
DepartmentChemistry & Biochemistry
Advisors
  • W.Grant McGimpsey, Advisor
  • Keywords
  • sensor
  • synthesis
  • bicyclic
  • fluoroionophore
  • nonactin
  • ion-selective
  • ammonium
  • Date of Presentation/Defense2003-05-01
    Availability unrestricted

    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.

    Files
  • msyavuz.pdf

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