LE3 .A278 2020

2020

Lukeman, Matthew

Acadia University

Bachelor of Science

Honours

Chemistry

Chemistry

Phenols experience an increase in acidity when excited to their singlet excited state. When this occurs, they may undergo an excited state intramolecular proton transfer (ESIPT) reaction, where the acidic proton on the hydroxyl group will transfer to a basic site on the same molecule. This research aims to increase the quantum yield of these reactions by adding R groups of increasing size to the 6-position on 2-phenylphenol (13). 6-Ethyl-2-phenylphenol (29) and 6-iso-propyl-2-phenylphenol (30) were prepared via bromination and Suzuki coupling, giving yields of 29% and 9%, respectively. These were then studied using IR spectroscopy and product studies. 1H and 13C{1H} NMR spectroscopy were used to determine deuterium incorporation and thus determining quantum yields. Both 29 and 30 underwent ESIPT and reverse proton transfer (RPT), giving a lower limit of F=0.40. IR data indicated that with increasing size of the added R groups, the molecule will preferentially adopt a conformation where the phenol OH is oriented toward the phenyl ring. These results are consistent with the hypothesis that increasing size of R groups added at the 6-position will increase quantum yields of ESIPT.

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https://scholar.acadiau.ca/islandora/object/theses:3459