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Synthesis of Nitrogen-Carbon-Nitrogen-Boron (NCNB) and Nitrogen-Boron-Nitrogen (NBN) zwitterions via a multicomponent reaction

Lee, Dong 2020. Synthesis of Nitrogen-Carbon-Nitrogen-Boron (NCNB) and Nitrogen-Boron-Nitrogen (NBN) zwitterions via a multicomponent reaction. MPhil Thesis, Cardiff University.
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Graphene is considered one of the most promising materials in modern industry. However, the absence of a band gap in graphene critically hinders its application in the field of semiconductors. In order to overcome this drawback, extensive research has been undertaken to fabricate graphene-like materials that possess a band gap. In this context, the development of Boron-Nitrogen doped polycyclic aromatic hydrocarbons (PAHs) with the aim of producing graphene-like semiconducting materials is one of the most widely studied areas in organic chemistry. This high interest towards these BN doped molecules derives from the fact that both computational and experimental studies proved BN doping to be an efficient method to finely tune the HOMO-LUMO gap of organic molecules. As a result, various synthetic routes for BN doped PAHs have been researched. Nevertheless, efficient methods for the synthesis of BN doped systems are needed as currently they are obtained in low yields by multi-stage synthetic strategies. Therefore, this project proposes a simpler potential synthetic route for this kind of materials via a multicomponent reaction. The work described in this thesis focuses on the development of a potential new synthetic pathway for BN doped molecules with the final aim of its exploitation for graphene doping. The first chapter delivers a brief introduction XVI XVII to graphene doping especially focused on the concept of 'BN doping', followed by a short description of some examples of multicomponent reactions such as the Biginelli and Ugi reactions. Finally, the Sugasawa reaction is described as it constitutes a sort of starting point for this work. In chapter 2, through the introduction of a previously studied reaction from the Bonifazi group, we report our investigation of a proposed multicomponent reaction that can help in finding a possible solution for the synthetic challenge of graphene doped systems. Chapter 3 addresses the initial investigation of the feasibility of reagents bearing functional groups such as carbonyl and nitrile for the proposed one-pot process. This chapter then describes how nitrile reagents could take part in the reaction leading to the formation of two different combinations of heteroatoms (NCNB and NBN) in the newly formed heterocycles in the products with a Zwitterion. Chapter 4 presents our attempts to optimise the one-pot synthesis process. In chapter 5, the investigation of the new multicomponent reaction with different starting reagents is summarised. In this summary, three different conditions of reactions are highlighted. Lastly, in chapter 6, all the information of the experimental details is reported to support all the scientific work that was done in this project.

Item Type: Thesis (MPhil)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 16 September 2020
Last Modified: 16 Sep 2021 01:30

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