Synthesis and Characterization of a Series of Benzylated Diazapyreniums
Date
2020-04-28
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Abstract
This thesis is focused on the synthesis of a series of benzylated diazapyrenium derivatives and their associated optical, electrochemical and supramolecular characteristics. In comparison to its analogues – bipyridinium, naphthalene diimide, and pyrene – diazapyrene has not received the same level of attention, and thus presents itself as an attractive electron-deficient, rigid, π-conjugated material for study. As such, a series of benzylated diazapyrenium species were designed to probe the effect of podality and relative spatial orientation on physical properties and halide recognition. Chapter One provides the basic conceptual foundation on which the material in this thesis was built and describes the breadth of work that has thus far utilized diazapyrenium species. The motivation for the application of the benzylated diazapyrenium derivatives – sensing of halides with an emphasis on fluoride – is also described. Chapter Two discusses the synthetic pathways and associated challenges in producing the benzylated diazapyrenium derivatives. This chapter includes an introduction that details a previously undertaken project that provided the groundwork for the synthesis of the benzylated diazapyrenium species, which are detailed in the second part of the chapter. The third chapter highlights the physical properties of the benzylated diazapyrenium series and responses to bromide, chloride, and fluoride. In line with previous studies that demonstrated unusual interactions between fluoride and electron-deficient, π-conjugated materials, this chapter highlights the interesting spectral responses of the synthesized diazapyrenium compounds upon exposure to fluoride. The physical characteristics and recognition events of the benzylated diazapyrenium series were probed via optical, NMR, electrochemical, and DFT methods. Finally, this thesis concludes with the primary conclusions and immediate outlook on the synthesized series of benzylated diazapyrenium compounds.
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chemistry
Citation
Jensen, G. E. (2020). Synthesis and Characterization of a Series of Benzylated Diazapyreniums (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.