Identifier

etd-0906102-155832

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."

Publisher

Worcester Polytechnic Institute

Degree Name

MS

Department

Chemistry & Biochemistry

Project Type

Thesis

Date Accepted

2002-09-06

Accessibility

Unrestricted

Subjects

Ionophores, Fluoroionohpores, Optical Sensors, Ionophores, Blood, Analysis, Ammonium compounds

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