Date of Award

2001

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Robert M. Strongin

Abstract

Resorcinarenes are a unique class of cyclic aromatic tetramers that have been known for over a century. In our laboratories, we have reported the first synthesis, isolation, and characterization of resorcinarenes with arylboronic acid functionality their framework. The physical property studies of our new resorcinarene series resulted in covalent and non-covalent binding studies, which revealed the first evidence chair (c2h) resorcinarenes can compete effectively with their crown (c4v ) counterparts the binding of polar guests (i.e. carbohydrates). In addition, the chiral tetraarylboronate octols have demonstrated potential utility as substrates for stereoselective extractions carbohydrates. A facile method for detecting and monitoring saccharides is of immense importance to medical diagnostics and industry. Molecular recognition studies in laboratories have led to the discovery of the most versatile colorimetric sensing test saccharides to date, which allows for the visual discrimination of 11 different saccharides of biological importance. Our colorimetric test is amenable carbohydrates, glucose phosphates, amino sugars, carboxylic acid sugars, oligosaccharides. Importantly, our pioneering efforts utilizing resorcinol-based synthetic receptors affords a simple, rapid, inexpensive, and fully reproducible colorimetric test.

ISBN

9780493271729

Pages

95

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