Identifier

etd-11142007-183128

Degree

Master of Science (MS)

Department

Chemistry

Document Type

Thesis

Abstract

The spectroscopic properties of a chiral boronic acid based resorcinarene macrocycle employed for chiral analysis were investigated. Specifically, the emission and excitation characteristics of tetraarylboronate resorcinarene macrocycle (TBRM) and its quantum yield were evaluated. The chiral selector TBRM was investigated as a chiral reagent for the enantiomeric discrimination of amino acids using steady-state fluorescence spectroscopy. Chiral recognition of amino acids in the presence of the macrocycle was based on diastereomeric complexes. Results demonstrated that TBRM had better chiral discrimination ability for lysine as compared to the other amino acids. Partial-least-squares regression modeling (PLS-1) of spectral data for macrocycle-lysine host-guest complexes was used to correlate the changes in the fluorescence emission for a set of calibration samples consisting of TBRM in the presence of varying enantiomeric compositions of lysine. In addition, validation studies were performed using an independently prepared set of samples with different enantiomeric compositions of lysine. The results of multivariate regression modeling indicated good prediction ability of lysine which was confirmed by a root-mean-square percent relative error (RMS%RE) of 5.8%.

Date

2007

Document Availability at the Time of Submission

Release the entire work immediately for access worldwide.

Committee Chair

Isiah M. Warner

Included in

Chemistry Commons

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