Faculty Advisor or Committee Member
Dr. W. Grant McGimpsey, Advisor
"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."
Worcester Polytechnic Institute
Chemistry & Biochemistry
All authors have granted to WPI a nonexclusive royalty-free license to distribute copies of the work. Copyright is held by the author or authors, with all rights reserved, unless otherwise noted. If you have any questions, please contact firstname.lastname@example.org.
Dennen, Katherine Faye, "Synthesis of Ammonium, Sodium, and Potassium Fluoroionohpores" (2002). Masters Theses (All Theses, All Years). 1023.
Ionophores, Fluoroionohpores, Optical Sensors, Ionophores, Blood, Analysis, Ammonium compounds