Title

Second Generation Chiral Porphyrins: Hosts with Chiral Centers Above the Porphyin Plane for Chiral Recognition Studies

Author

Maha Alqurafi

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Fall 2014

Abstract

Cation and anion host-guest chemistry (ion recognition) are well-developed fields in supramolecular chemistry. A significant amount of work has been accomplished in molecular recognition as well. Within the field of molecular recognition, chiral recognition is an emerging area of research with diverse applications. This project centers on the synthesis and chiral recognition studies of chiral porphyrins characterized by the spatial positioning of asymmetric centers above the porphyrin surface which effectively serve to cap the porphyrin. Thus, these hosts have asymmetric centers positioned directly above the metal center. These hosts are fairly rigid and should magnify complementary guest binding interactions (such as hydrogen bonding, pi-pi interactions, metal coordination) for one enantiomer of a guest while minimizing steric interactions. For the creation of the hosts, a porphyrin isocyanate was reacted with a variety of commercially available chiral pyrrolidines. Guests studied were primarily chiral carboxylate-containing guests. Several of these hosts display a conformationally-induced organization upon binding to guests. The host synthesis, the NMR and Mass characterization of host compounds and their chiral molecular recognition properties is reported.

Advisor

Stephen D. Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

Share

COinS