Document Type thesis Author Name Dennen, Katherine Faye URN etd-0906102-155832 Title Synthesis of Ammonium, Sodium, and Potassium Fluoroionohpores Degree MS Department Chemistry & Biochemistry Advisors Dr. W. Grant McGimpsey, Advisor Keywords Ionophores Fluoroionohpores Optical Sensors Date of Presentation/Defense 2002-08-19 Availability unrestricted
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 calixarenearenecrown-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.
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