Worcester Polytechnic Institute Electronic Theses and Dissertations Collection

Title page for ETD etd-0906102-155832


Document Typethesis
Author NameDennen, Katherine Faye
URNetd-0906102-155832
TitleSynthesis of Ammonium, Sodium, and Potassium Fluoroionohpores
DegreeMS
DepartmentChemistry & Biochemistry
Advisors
  • Dr. W. Grant McGimpsey, Advisor
  • Keywords
  • Ionophores
  • Fluoroionohpores
  • Optical Sensors
  • Date of Presentation/Defense2002-08-19
    Availability unrestricted

    Abstract

    N-(1-methylpyrene) monoaza-15-crown-5 (P5), N-(1-methylpyrene) monoaza-18-crown-6 (P6), N-(9-anthryl-methyl) monoaza-15-crown-5 (A5), N-(9-anthryl-methyl) monoaza-18crown-6 (A6), were synthesized and tested as fluoroionophores for potassium and sodium cations. Upon metal ion complexation, fluorescence yields increased dramatically due to an internal photoinduced electron transfer quenching mechanism (an off-on fluorescence switch).

    The results for these model compounds led to the design and synthesis of 1,3 alternate calixarene[4]arenecrown-5 (I) and bicyclic peptide (V). Calixarene I was synthesized and found to selectively complex potassium cations as predicted.

    The design of bicyclic peptide V is directed toward the selective complexation of ammonium cations. The synthesis of V involved the preparation of an open chain hexa-peptide consisting of two trityl-protected homoserine residues. Addition of an amino methyl pyrene across two homoserine residues was attempted by triflating the alcohols. The cyclization of the peptide ring is expeded to produce a basket-like structure that molecular modeling indicates should have improved selectivity over that of nonactin, the current industry standard.

    Files
  • kdennen.pdf

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