- Synthesis and photophysical properties of 7-(diethylamino)-3-(4-(arylethynyl)phenyl)-2H-chromen-2-ones as strong fluorescent materials
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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.
- Asano, Naoto,Ishikawa, Tenta,Iwanaga, Tetsuo,Kitanou, Takayuki,Kobayashi, Kurumi,Oki, Tomohiro,Shibata, Mitsuhiro,Shimasaki, Toshiaki,Teramoto, Naozumi
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- MANUFACTURING METHOD OF COUMARIN DERIVATIVE, MANUFACTURING METHOD OF FLUORESCENT AGENT FOR COLORING AND MANUFACTURING METHOD OF DYE FOR FLUORESCENCE
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PROBLEM TO BE SOLVED: To provide an easier, low cost and high yield manufacturing method of 3-aryl-7-N,N-dialkyl aminocoumarin derivative. SOLUTION: There is provided a manufacturing method of 3-aryl-7-dialkyl aminocoumarin derivative represented by the formula (3) by reacting acrylic acids having a 4-amino-2-carboxy-phenyl group and further a phenyl group, dialkyl sulfate compound, Lewis acid at same time or in sequence in a same bath. (3), where Ar is a phenyl group, a thienyl group, a pyridyl group or a naphthyl group which may have a substituent, R3 is a C1 to 4 linear/branched alkyl group, R4 is H, C1 to 8 linear/branched alkyl group, benzyl group or the like. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0047; 0048
(2017/10/11)
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- Highly regioselective α-arylation of coumarins via palladium-catalyzed C-H activation/desulfitative coupling
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A novel regioselective α-arylation of coumarins with readily available arenesulfonyl chlorides and sodium arenesulfinates via palladium-catalyzed direct C-H functionalizations under mild reaction conditions is described. This protocol presents an unexpected and highly regio-controlled arylation of coumarins at C-3 to construct interesting 3-arylcoumarins with fascinating biological and fluorescent properties. The regioselectivity observed is in sharp contrast with that expected for the Heck reactions. Copyright
- Jafarpour, Farnaz,Olia, Mina Barzegar Amiri,Hazrati, Hamideh
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supporting information
p. 3407 - 3412
(2013/12/04)
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- Palladium-catalyzed decarboxylative cross-coupling reactions: A route for regioselective functionalization of coumarins
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A straightforward, regioselective, and step-economical ligand-free palladium-catalyzed decarboxylative functionalization of coumarin-3-carboxylic acids is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows for construction of various biologically important π-electron extended coumarins.
- Jafarpour, Farnaz,Zarei, Samaneh,Olia, Mina Barzegar Amiri,Jalalimanesh, Nafiseh,Rahiminejadan, Soraya
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p. 2957 - 2964
(2013/06/05)
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- PHOTOCHEMICAL REACTIONS OF 7-AMINOCOUMARINS. 6. REACTION OF 7-DIALKYLAMINOCOUMARINS WITH HALO DERIVATIVES
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3-Substituted 7-dialkylaminocoumarins were synthesized as a result of the photoreaction of 7-diethylaminocoumarin, 4-trifluoromethyl-7-diethylaminocoumarin, 4-chloro-7-diethylaminocoumarin, 4-(N-morpholino)-7-diethylaminocoumarin, and coumarin-102 (2,3,6,
- Kirpichenok, M. A.,Mel'nikova, L. M.,Denisov, L. K.,Grandberg, I. I.
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p. 858 - 862
(2007/10/02)
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