CHED 685 |
| Anthracene bisimide derivatives are an under-investigated class of fluorescent dyes mainly due to synthetic difficulties and solubility limitations. A new route to the synthesis of anthracene bisimides was recently developed that utilizes the photoenolization of o-methylbenzophenones. This new class of chromophore was characterized as having visible absorption, green fluorescence, and photostability in the presence of oxygen. A systematic series of these fluorescent derivatives has already been synthesized and characterized. This study demonstrated a correlation between the charge-transfer state and the cumulative inductive effects of the substituents. Five additional anthracene bisimide derivatives have been synthesized with the following R substituents: tert-butyl benzene (1), benzo 15-crown-5 (2), methyl 18-crown-6 (3), triphenyl amine (4), and phenyl boronic acid (5), and their chemosensory behavior has been investigated. These new fluorescent dyes were characterized via absorption and emission spectroscopy, including excited-stated kinetic, extinction coefficient, and quantum yield measurements. Anthracene bisimides 1, 3, and 5 did not show any sensing behavior. However, two bisimide derivatives, 2 and 4, showed the potential to be “on-off” sensors. Compound 2 detected metal cations, such as sodium, and compound 4 revealed the presence of nitroaromatic compounds, including 2,4-dinitrotoluene,. Interestingly, these two anthracene bisimide derivatives showed an eximer effect in non-polar solvents. Current research is underway to quantify the sensing behavior of anthracene bisimide dyes 2 and 4. |
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Undergraduate Research Poster Session: Polymer Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster
Division of Chemical Education |