Document Type

Thesis

Degree

Master of Science (MS)

Department

Chemistry

First Advisor's Name

Konstantinos Kavallieratos

First Advisor's Committee Title

Committee Chair

Second Advisor's Name

Watson J. Lees

Third Advisor's Name

Kenneth G. Furton

Date of Defense

11-23-2005

Abstract

The synthesis and anion binding properties of a fluorescent tripodal n-dansylamide (2) and a redox active tripodal quinone-based (3) receptor derived from 1,3,5-tris-(aminomethyl)-2,4,6-triethylbenzene. Herein the investigation of anion binding by these receptors via 1H-NMR, FT-IR, UV-Visible, and (APCI-MS) is reported. Fluorescence and electrochemical studies determined the ability of these receptors to sense anions. The downfield chemical shift changes in the 1H-NMR spectra and the low energy shifts of the νN-H stretching frequency in the FT-IR spectra indicated anion binding via hydrogen bonding. The binding constants for anion-receptor complex formation were determined and indicate a preference of receptor 2 for the binding of nitrate over chloride, bromide and iodide, while receptor 3 was also found to be selective for binding nitrate over chloride. For receptor 2, the 1:1 anion-receptor binding stoichiometry was confirmed by fluorescence Job plots and the 1:1 anion-receptor supramolecular complexes were identified by APCI-MS.

Identifier

FI14061574

Comments

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Chemistry Commons

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