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UBC Theses and Dissertations

Phosphorus-containing macromolecules for fluorescence-based sensing applications Mackenzie, Harvey Kyle


This thesis outlines the synthesis and properties of phosphorus containing polymers and their model compounds. The incorporation of phosphorus in these systems leads to interesting photophysical properties that are dependent on the chemical environment of the phosphorous atoms. The photophysical properties of these materials can be useful for fluorescent based sensing. Small-molecule model compounds were used for testing the viability of various alkynes for polymerization. Notably the synthesized model compounds were shown to display an affinity for metal salts, specifically for gold(I) and gold(III). Fluorenyl and thiophene containing derivatives were also synthesized along with the first example of a thiophene containing poly(p-phenylenediethynylene phosphine) (PPYP). These systems undergo fluorescence upon oxidation of the phosphorus centers and could be useful for the detection of reactive oxygen species. To increase the emissive properties of PPYPs, fluorenyl-containing derivatives were synthesized. These polymers were shown to be highly emissive upon oxidation (Φsoln = 0.30) and were tested as fluorescent-based sensors for a variety of metal analytes. Interestingly, the polymers and their corresponding model compounds displayed a large fluorescence increase upon coordination to gold(I) and gold(III) while the presence of other metals such as Rh(I) resulted in no significant fluorescence response. This research represents the first use of a polymer as a fluorescence-based sensor for the detection of gold ions.

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