Preparation, Properties, and Future Directions of Novel Zig-zag Edged Nanographenes
Authors
Anderson, Hannah
Issue Date
2023
Type
Dissertation
Language
Keywords
Benzannulation , Nanographenes , PAH , Zig-zag edge
Alternative Title
Abstract
Graphene is a benchmark material in the field of organic electronics due to its many intriguing properties, such as conductivity, flexibility, and single-atom thickness. Nanographenes are a smaller subset of graphene, possessing similar properties but also displaying some additional ones, such as semiconducting abilities, that allow for improved application in organic electronic devices. Over the past few decades, nanographene synthesis has become a booming field, with many synthetic techniques still being developed. Some of the many methods include Scholl cyclization, transition-metal catalyzed coupling, and cycloadditions, and a particular area of interest involves synthesis through alkyne benzannulation. The Chalifoux group has previously used alkyne benzannulation methods to prepare a variety of pyrene-based structures, including some with zig-zag edges. Nanographenes with extended zig-zag edges can possess their own set of unique properties, such as singlet-oxygen sensitizing capabilities or interesting magnetic behavior, which makes them particularly interesting, but also particularly challenging targets for synthesis and characterization. This dissertation will outline some of the first steps that we have made toward synthesizing a series of zig-zag edged nanographenes with gradually increasing sizes, with the ultimate goal of inducing diradical character in the longest analogues.