Title

Prolinesulfonamide-Porphyrin Derivatives: 19F-Nmr and Uv Detection of Chiral Recognition for Anions and Amines

Author

Minghsun Yang

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Fall 2012

Abstract

There is a current research interest in the recognition of molecules, particularly of molecules with chiral centers that have specific interactions in bio-systems or in human physiology. The identification of a particular species and the concentration of chiral molecules in a matrix is difficult to determine in a timely and accurate manner. The objective of this project is to design and synthesize hosts to recognize chiral molecules specifically rather than to create a novel and convenient analytical method. The target chiral molecules are amino acids, alkaloids, such as nicotine and ephedrine, and some medications with a carboxylate motif, such as ibuprofen and naproxen. These molecules feature one or more chiral centers and contain a substituent that is a hydrogen bond donor or acceptor. Taking into consideration the features of a chiral molecule, we report here the design and recognition studies of host molecules that complement the shape and binding motifs of target molecules. The goals of this project will be accomplished by investigating the following hypothesis: Selective receptors for chiral guests can be developed by rational host design. To achieve selective chiral recognition, the host should be designed in such way that the guest recognition elements are pre-positioned in a manner that precisely complements the asymmetric shape, the functionality, the size, and the charge of the guest.

Advisor

Stephen Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

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