Synthesis and photophysical properties of 7-(diethylamino)-3-(4-(arylethynyl)phenyl)-2H-chromen-2-ones as strong fluorescent materials
3-(4-(Arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-ones 1a‒1d were synthesized by Pd/Cu-catalyzed Sonogashira cross-coupling reactions. After the structural properties were examined by the X-ray crystal analysis, their photophysical properties including fluorescence properties in solid states w...
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Veröffentlicht in: | Tetrahedron 2021-09, Vol.96, p.132369, Article 132369 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 3-(4-(Arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-ones 1a‒1d were synthesized by Pd/Cu-catalyzed Sonogashira cross-coupling reactions. After the structural properties were examined by the X-ray crystal analysis, their photophysical properties including fluorescence properties in solid states were systematically studied. It was revealed that the pyrenyl derivative 1d showed high fluorescence quantum yield (ΦF = 0.87) in a THF solution, and that the phenyl derivative 1a exhibited an intense fluorescence (Φsolid = 0.15) even in a solid state. According to the TDDFT calculations, the HOMOs of compounds 1a and 1b are mainly located on the 3-(4-(arylethynyl)phenyl)-7-(diethylamino)-2H-chromen-2-one moieties, whereas on the aryl moieties for 1c and 1d. The electrochemical studies revealed that the compounds 1a and 1b underwent reversible 1e− oxidations.
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2021.132369 |