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Hydrogen-Bonding Control of Solvatochromism and Non-Radiative Decay in the Fluorescence of 3-Aminofluoren-9-one Derivatives
Alty, Isaac Gregory
Alty, Isaac Gregory
Abstract
The object of this study is to determine whether in-plane or out-of-plane hydrogen bonds to solvent molecules more efficiently quench fluorescence in 3-aminofluoren-9-one systems. 3-Aminofluoren-9-one has a high quantum yield of fluorescence, and it exhibits strong fluorescence quenching in protic solvents. To determine the mode of hydrogen-bonding that leads to the greatest quenching, 3-aminofluoren-9-one and two derivatives, 3-amino-6,8-dimethylfluoren-9-one and 3-amino-1,8-dimethylfluoren-9-one were synthesized. The fluorescence of these molecules in various binary solvent mixtures was studied to determine the strength of quenching and shifts in fluorescence maxima in solvents of different polarity. Determination of the mode of solvent hydrogen-bonding that most efficiently quenches fluorescence in 3-aminofluoren-9-one will provide useful information on the quenching behavior of similar molecules. This will contribute to the development of more sensitive molecular probes for acidity of enzyme binding sites for use in biochemical and biomedical applications.
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2016-04-01
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Chemistry