Anion Recognition Properties of Chiral Porphyrin Atropisomers

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Date of Award

Summer 2021

Abstract

This project centered on the synthesis and study of multiple synthetic porphyrin-based hosts for recognition of anions and amines that could aid in sensor development for chiral compounds, chiral separations or the determination of enantiomeric excess of chiral mixtures. The porphyrin host compounds have an axis of chirality and thus exist as atropisomers. One aspect of the project is the synthesis of a porphyrin host that can function as a chiral molecular switch. The key aspect of the project is centered around the synthesis of a chiral porphyrin host consisting of a monoamino-tetraphenyl porphyrin scaffold with an arm containing an axis of chirality substituted on one of the four meso aryl groups. This design should position the chiral arm directly over the metal core creating a binding pocket for induced fit binding of target guests. The axial chirality of the host compounds stems from modification of an indole-phenyl core with various groups that will increase the rotational barrier around the indole-phenyl bond. Some of the host derivatives could thus contain a mechanism for a switching stimuli to respond to the 3-dimensional structure of a guest molecule. Depending on the absolute stereochemistry of the guest, the host could exist in one of two atropisomeric forms. A computational study has also been conducted to study the effects of the addition of substituents at various locations on the indole-phenyl arm for the determination of the effect on the rotational barrier; the systems studied computationally are model compounds for the host compounds discussed here.

Advisor

Stephen D. Starnes

Subject Categories

Chemistry | Physical Sciences and Mathematics

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