Electronic Finetuning of 8‐Methoxy Psoralens by Palladium‐Catalyzed Coupling: Acidochromicity and Solvatochromicity
| Autor: | Christian Ganter, Torsten Hölzel, Sarah R. Geenen, Lysander Presser, Thomas Müller |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
solvatochromism
Sonogashira coupling chemistry.chemical_element Electronic structure Heterocycles 010402 general chemistry Photochemistry 01 natural sciences Catalysis Coupling reaction Ultraviolet visible spectroscopy cross-coupling reactions Heck reaction UV/Vis spectroscopy Full Paper 010405 organic chemistry Chemistry Organic Chemistry Solvatochromism General Chemistry Full Papers Fluorescence 0104 chemical sciences acidochromism density functional calculations donor–acceptor dyes Palladium |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| Popis: | Differently 5‐substituted 8‐methoxypsoralens can be synthesized by an efficient synthetic route with various cross‐coupling methodologies, such as Suzuki, Sonogashira and Heck reaction. Compared to previously synthesized psoralens, thereby promising daylight absorbing compounds as potentially active agents against certain skin diseases can be readily accessed. Extensive investigations of all synthesized psoralen derivatives reveal fluorescence in the solid state as well as several distinctly emissive derivatives in solution. Donor‐substituted psoralens exhibit remarkable photophysical properties, such as high fluorescence quantum yields and pronounced emission solvatochromicity and acidochromicity, which were scrutinized by Lippert–Mataga and Stern–Volmer plots. The results indicate that the compounds exceed the limit of visible light, a significant factor for potential applications as an active agent. In addition, (TD)DFT calculations were performed to elucidate the underlying electronic structure and to assign experimentally obtained data. A diverse and colorful library of novel psoralens can be obtained by cross‐coupling reactions of 5‐bromo‐8‐methoxypsoralen, which was prepared by a novel multistep synthesis. Photophysical properties, such as emission solvatochromicity and acidochromicity make this class of functional chromophores particularly attractive. |
| Databáze: | OpenAIRE |
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