Synthesis, luminescence properties, and theoretical insights of N-alkyl- or N,N-dialkyl-pyrene-1-carboxamide |
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Authors: | Yosuke NikoSusumu Kawauchi Gen-ichi Konishi |
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Institution: | a Department of Organic and Polymeric Materials, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo 152-8552, Japan b PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama 332-0012, Japan |
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Abstract: | We report the synthesis and photophysical properties of N-alkyl- or N,N-dialkyl-pyrene-1-carboxamide. These derivatives, as well as pyrene, exhibited blue emission. N-Alkyl-type derivatives exhibited strong fluorescence emission (Φfl = 0.61 in EtOH) in both nonpolar and polar solvents. On the other hand, N,N-dialkyl-type derivatives showed weak fluorescence emission (Φfl <0.01) due to vibrational deactivation. However, in highly viscous solvents such as glycerin, the quantum efficiencies of N-alkyl-type (Φfl = 0.91) and N,N-dialkyl-type (Φfl = 0.082) derivatives were increased. We also investigated the fluorescence mechanism of these compounds using time-dependent density-functional theory (TD-DFT). From these results, we find that highly fluorescent pyrene-1-carboxamide derivatives can be designed by introducing an appropriate functional group at the nitrogen atom of the amide. Thus, N,N-dialkyl-type pyrene-1-carboxamide has considerable potential for use in applications such as environmental response sensors and probes. |
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Keywords: | Pyrene Pyrenecarboxamide Fluorescent Fluorescence quantum yield DFT theory |
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