Synthesis, structure and function of oligo(1,8-pyrenylenes)

Walsh, Joshua C. (2021) Synthesis, structure and function of oligo(1,8-pyrenylenes). Doctoral (PhD) thesis, Memorial University of Newfoundland.

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Abstract

This thesis is divided into four chapters. Chapter 1 will show progress towards a review of applications utilizing the pyrene core to show the utility of one of the most studied molecules in chemistry is far from fully realized. Chapter 2 shows a monomer‐through-pentamer series of oligo(1,8‐pyrenylene)s was synthesized using a two‐step iterative synthetic strategy. The trimer, tetramer and pentamer are mixtures of atropisomers that interconvert slowly at room temperature (VTNMR analysis). They are classified as functional molecular liquids (FMLs) well below room temperature, as indicated by POM, DSC and SWAXS analysis. The oligomers are highly fluorescent both in the liquid state and in dilute solution and an investigation of their photophysical properties demonstrated that delocalization plays a larger role in their excited states than it does in related pyrene‐based oligomers. Chapters 3 and 4 outline progress in using the oligomers as starting points for different molecular systems will also be covered, attempting to put more ‘F’ in the FMLs.

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