ORGN 670 |
| David E. Lewis1, Kristy A. McNitt2, Nicholas R. Deprez1, and Robert G. Brown3. (1) Department of Chemistry, University of Wisconsin-Eau Claire, Eau Claire, WI 54702, (2) Department of Chemistry, University of Wisconsin - Eau Claire, Eau Claire, WI 54702, (3) School of Applied Sciences, University of Glamorgan, Pontypridd, CF37 1DL, United Kingdom |
| Tröger's bases (methanodibenzodiazocines) have attracted a great deal of interest since their first synthesis in 1887 We have prepared a series of fluorescent Tröger's bases containing the naphthalimide fluorophore treatment of N-alkyl-4-amino-1,8-naphthalimides with formalin and concentrated hydrochloric acid in ethanol. Depending on the reactant, this reaction gives a seco-Tröger's base when the reaction is carried out at ambient temperatures, and the Tröger's base when the reaction is carried out at elevated temperature. These dimeric naphthalimides exhibit solvent-dependent fluorescent behavior which involves, inter alia, a reduction in fluorescence quantum yields by up to two orders of magnitude in polar solvents compared to cyclohexane. The synthesis and photophysics of these dimeric naphthalimide dyes will be discussed. |
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |