Dokument: T‐Shaped 8‐Aryl(ethynyl)‐Substituted Psoralens With Tunable Charge‐Transfer Absorption
| Titel: | T‐Shaped 8‐Aryl(ethynyl)‐Substituted Psoralens With Tunable Charge‐Transfer Absorption | |||||||
| URL für Lesezeichen: | https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=73182 | |||||||
| URN (NBN): | urn:nbn:de:hbz:061-20260505-123121-9 | |||||||
| Kollektion: | Publikationen | |||||||
| Sprache: | Englisch | |||||||
| Dokumententyp: | Wissenschaftliche Texte » Artikel, Aufsatz | |||||||
| Medientyp: | Text | |||||||
| Autoren: | Leusch, Lena T. [Autor] Müller, Thomas J. J. [Autor] | |||||||
| Dateien: |
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| Stichwörter: | donor–acceptor dyes , fluorescence , density functional theory calculations , solvatochromism , acidochromism , cross-coupling reactions | |||||||
| Beschreibung: | Two series of novel T-shaped 8-substituted psoralen derivatives bearing (hetero)aryl and arylethynyl substituents were synthesized via Suzuki and Sonogashira coupling starting from 8-methoxypsoralen (8-MOP). Predominantly, electron-donating substitutents such as anisyl and phenothiazine were introduced at the 8-position of the psoralen for increasing the electron density in comparison to 8-MOP. Photophysical properties were studied by absorption and emission spectroscopy in solution and in the solid state. Increasing the donor strength of the substituent causes a bathochromic shift of both absorption and emission maxima. The absorption behavior can be correlated with Hammett substituent parameters of remote substituents at the p-aryl moieties that are directly or by ethynyl spacing positioned at the 8-position of psoralen. In most cases, fluorescence in the solid state is more pronounced than in solution. One derivative also displays significant aggregation-induced emission. For two amino-substituted psoralen derivatives, positive emission solvatochromism was observed and associated with a considerable change of dipole moment upon photonic excitation according to Lippert–Mataga analysis. Furthermore, the pKa value of the T-shaped dimethylaminophenyl psoralen derivative was determined from absorption spectra. In addition, emission quenching is caused by protonation on the nitrogen atom. TD-DFT (time-dependent density functional theory) calculations are in good agreement with experimental data and rationalize the electronic structure. | |||||||
| Rechtliche Vermerke: | Originalveröffentlichung:
Leusch, L., & Müller, T. J. J. (2026). T‐Shaped 8‐Aryl(ethynyl)‐Substituted Psoralens With Tunable Charge‐Transfer Absorption. European Journal of Organic Chemistry, 29(8), Article e202501175. https://doi.org/10.1002/ejoc.202501175 | |||||||
| Lizenz: |  Dieses Werk ist lizenziert unter einer Creative Commons Namensnennung 4.0 International Lizenz | |||||||
| Fachbereich / Einrichtung: | Mathematisch- Naturwissenschaftliche Fakultät | |||||||
| Dokument erstellt am: | 05.05.2026 | |||||||
| Dateien geändert am: | 05.05.2026 |
