Thesis Format

Integrated Article

Extending the Conjugation of Boron Difluoride Formazanate Dyes Using Alkyne Linkages

Author

Erin L. Cotterill, The University of Western OntarioFollow

Degree

Master of Science

Program

Chemistry

Supervisor

Gilroy, Joe. B

Abstract

This thesis describes the synthesis and characterization of alkyne-linked BF₂ formazanate dyes and the effects of extending 𝜋-conjugation through alkyne linkages. Chapter 2 examines the design of platinum-centered oligoynes capped by BF₂ formazanates. These compounds exhibit high stability and solubility, panchromatic absorption, and redox activity. Thin-film studies demonstrate that incorporating a [Pt(PBu₃)₂]²⁺ unit into the oligoyne backbone influences conductivity on the microscale and nanoscale when compared to metal-free oligoynes. Chapter 3 explores the random copolymerization of BF₂ formazanate dyes with fluorene or bis(alkoxy)benzene units through Glaser-Hay coupling. The copolymers exhibit redox activity and broad absorption of UV-visible light. The alkyne linkages of the copolymers are reacted with dicobaltoctacarbonyl, demonstrating the ability to tune optical properties through structural variation. Together, this work demonstrates the ability to tune the properties of BF₂ formazanates by extending 𝜋-conjugation through alkyne linkages, leading to potential applications in the field of organic electronics.

Summary for Lay Audience

This thesis describes the synthesis of highly-coloured molecules and polymers (chains of molecules) that absorb ultraviolet and visible light. Within the scientific community, it is desirable to design a broad scope of materials that absorb and emit a large range of colours for use in organic electronics, such as solar panels and light-emitting diodes. Conjugated molecules, which are comprised of alternating single and double/triple bonds, are often used in these types of applications. By adjusting the number of alternating single and double/triple bonds, different colours of light can be absorbed or emitted. The molecules and polymers synthesized within this thesis exhibit broad absorption of UV-visible light, meaning they would have the ability to absorb sunlight efficiently, which may lead to the fabrication of solar cell devices with superior performance compared to current technology. Some of the conjugated molecules within this thesis were shown to act as semiconductors, meaning they were able to transport electricity. The materials synthesized within this thesis are particularly good candidates for use in field-effect transistors, which control the flow of current in digital circuits.

Recommended Citation

Cotterill, Erin L., "Extending the Conjugation of Boron Difluoride Formazanate Dyes Using Alkyne Linkages" (2024). Electronic Thesis and Dissertation Repository. 10470.
https://ir.lib.uwo.ca/etd/10470

Creative Commons License

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