The π-conjugation length determines the fluorescence quenching mechanism of aromatic aldehydes in water
Water-soluble distyrylbenzene-based aldehydes are excellent fluorescence turn-on indicators for amine detection, since they are themselves non-fluorescent in water. Here, the fluorescence quenching mechanisms of aldehydes with systematically increasing π-systems are investigated in an aqueous enviro...
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| Main Authors: | , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
20 July 2018
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| In: |
Chemical physics
Year: 2018, Volume: 515, Pages: 710-718 |
| DOI: | 10.1016/j.chemphys.2018.07.008 |
| Online Access: | Verlag, Volltext: https://doi.org/10.1016/j.chemphys.2018.07.008
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| Author Notes: | Katharyn Fletcher, Maximilian Krämer, Uwe H.F. Bunz, Andreas Dreuw |
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| 520 | |a Water-soluble distyrylbenzene-based aldehydes are excellent fluorescence turn-on indicators for amine detection, since they are themselves non-fluorescent in water. Here, the fluorescence quenching mechanisms of aldehydes with systematically increasing π-systems are investigated in an aqueous environment using quantum chemical methods. Although the aldehydes are structurally related, with each extension of the π-system the fluorescence quenching mechanism changes from excited-state hydrogen transfer to trans→cis isomerization and nπ∗ state-mediated intersystem crossing, until the aldehydes become fluorescent in water. For distyrylbenzene aldehyde, nπ∗ mediated ISC has been identified as major fluorescence quenching channel, which becomes closed upon reaction with an amine explaining its fluorescence turn-on sensitivity. | ||
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