The π-conjugation length determines the fluorescence quenching mechanism of aromatic aldehydes in water

• Verfasst von: Fletcher, Katharyn M. [VerfasserIn]
• Verfasst von: Krämer, Maximilian [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Verfasst von: Dreuw, Andreas [VerfasserIn]
• Titel: The π-conjugation length determines the fluorescence quenching mechanism of aromatic aldehydes in water
• Verf.angabe: Katharyn Fletcher, Maximilian Krämer, Uwe H.F. Bunz, Andreas Dreuw
• E-Jahr: 2018
• Jahr: 20 July 2018
• Umfang: 9 S.
• Fussnoten: Gesehen am 22.04.2020
• Titel Quelle: Enthalten in: Chemical physics
• Ort Quelle: Amsterdam [u.a.] : Elsevier Science, 1973
• Jahr Quelle: 2018
• Band/Heft Quelle: 515(2018), Seite 710-718
• DOI: doi:10.1016/j.chemphys.2018.07.008
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 169564039X

Abstract

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.