Date of Submission

Spring 2018

Academic Programs and Concentrations

Chemistry

Project Advisor 1

Justin Foy

Abstract/Artist's Statement

Artificial molecular machines aim to bridge the gap between molecular systems and macroscopic processes. As more complex systems emerge that can perform molecular-scale work, an increasing area of emphasis is scaling up the nanometer motions of artificial molecular machines to accomplish large-scale mechanical work. Azobenzene is an extensively studied molecular switch that undergoes light-driven cis-trans isomerization. The incorporation of azobenzenes into macrocycles and implementation into polymeric materials is promising for converting molecular-level photoswitching into large-scale mechanical work. This project focuses on the initial synthetic steps towards a new azobenzenophane synthon 2 for incorporation into light-responsive materials by way of a bisdibenzazocine functional group. A methodology for synthesizing intermediate bis(2-bromo-5-nitrophenyl)methane has been developed in this research. Its optimization and use as a starting material for the azobenzenophane synthetic target are detailed. Also discussed is the synthesis of a novel azobenzene switching model to be implemented into a macrocycle. In addition to continued synthetic work towards the azobenzenophane target, further research into the photoisomerization of the azobenzene macrocycle and its assessment for application into materials will be conducted.

Open Access Agreement

On-Campus only

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.

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