Title page for ETD etd-0906102-155832

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

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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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
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