Document Type

Thesis

Degree Name

Master of Science (MSc)

Department

Chemistry

Faculty/School

Faculty of Science

First Advisor

Dr. Kenneth E. Maly

Advisor Role

Supervisor

Abstract

In this thesis, the synthesis of a series of brominated alkoxy-substituted trinaphthylenes was developed using a nickel-mediated Yamamoto coupling as the main step. Characterization of these compounds led to the discovery of a new set of broad range liquid crystals. They were found to undergo higher order transitions (i.e. glass phases/soft crystals/liquid crystal) via DSC, and also to decompose before reaching an isotropic liquid, as verified via thermogravimetric analysis. Polarized optical microscopy showed a texture characteristic of a columnar hexagonal mesophase. In addition, the aggregation in solution was studied using concentration dependent NMR studies, and the brominated-derivatives were determined to have an association constant 29 times greater than the trinaphthylene precursors. The precursors were newly synthesized via the Yamamoto coupling reaction in moderate yields with a facile purification, however did not show any mesomorphic properties.

In addition, the synthesis of a large starphene bearing long alkoxy chains and ethynyl-TMS groups was attempted. The synthesis of this compound was ultimately unsuccessful, and the challenges are summarized herein. Furthermore, a new method was found in the preparation of tetranaphthylene by simply varying the concentration of the Yamamoto reaction solution.

Convocation Year

2017

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