Photoinduced formation of the laser dye coumarin 6 from its dihydro derivatives

Traven, V. F.; Cheptsov, Dmitrii A.; Solovjova, Natalya P.; Чибисова, Т. А.; Voronov, Ilya I.; Dolotov, S. M.; Иванов, И. В.

doi:10.1016/j.dyepig.2017.07.001

Cited by 27 publications

(8 citation statements)

References 23 publications

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“…Coumarin derivatives represent an important class of heterocyclic compounds possessing many significant electro-optical properties as well as showing different biological activities. − These molecular scaffolds are generally characterized by high fluorescence, large Stokes shifts, high photoluminescence quantum yield (PLQY), sensitivity, dual emission, internal charge transfer (ICT), and twisted ICT properties. , For all of these reasons, coumarin adducts find application in various research fields such as laser dyes, organic light-emitting diode fabrication, and dye-sensitized solar cells as cell-imaging biomarkers or optical brighteners . The visible absorption properties of such compounds are highly controlled by the insertion of various substituents directly bonded to the heteroaromatic structure, and in particular, coumarin functionalization by the insertion of electron-donating groups (EDGs) in the positions C5 or C7 and electron-withdrawing groups (EWGs) in the positions C3 or C4 has been previously investigated .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives

et al. 2021

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A series of 6-aryl coumarin dyes were synthesized in satisfactory yields by Pd-catalyzed Suzuki cross-coupling reactions with a panel of boronic acids and coumarin bromides. Photophysical studies highlighted a large Stoke shift and interesting fluorescence quantum yield for these compounds. Optical properties were also investigated with the aid of quantum chemical calculations. The treatment of selected coumarin dyes with increasing amounts of trifluoroacetic acid showed that their fluorescence can be strongly influenced by pH (fluorescence quenching at high acid concentrations), while the addition of Fe 3+ and Al 3+ metal ions allowed to highlight dichotomous behavior with the corresponding reduction in fluorescence with the increase of [Fe 3+ ] or [Al 3+ ]. Finally, biological assays and fluorescence microscopy imaging investigations indicated that these compounds can be used as potential biomarkers in living and fixed cells.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives

et al. 2021

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“…Furthermore, the photophysical properties of coumarin-based fluorescent dyes have shown the advantage of using the benzopyran moiety as a fluorogenic scaffold [ 8 ]. Various coumarin-based compounds were applied in fields as laser dyes [ 9 ], cell-imaging biomarkers [ 10 ], and optical brighteners [ 11 ].…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

Lyapchev

Koleva

et al. 2022

Molecules

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Quantum-chemical calculations on the spectral properties of some aryl substituted 3-phosphonocoumarins were performed, and the effect of the substituents in the aryl moiety was evaluated. The structures possessing promising fluorescent properties were successfully synthesized via Suzuki and Sonogashira cross-coupling. The synthetic protocol was also applied for the phosphorous chemoisomer of 3-phosphonocoumarin, 1,2-benzoxaphosphorin, and their carboxylate analogues. The optical properties of the arylated and alkynylated products were experimentally determined. The obtained quantum-chemical and experimental results give the possibility for a fine tuning of the optical properties of phosphorous-containing coumarin systems by altering the substituent at its C-6 position.

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“…In the past decade, benzocoumarins, as the building block embedded in many natural products and biologically active molecules, have attracted considerable attention. − As a “privileged” scaffold, coumarins show rewarding biological properties, especially for their anti-HIV , and antibiotic activities, , such as natural microorganism antibiotic WS-5995A . In addition, π-expanded coumarins have been used in various research areas because of their unique photophysical , and photochemical properties, − such as organic light-emitting materials, laser dyes, liquid crystal materials, and fluorescent probes . The unique prominence of π-expanded coumarin in fluorescent material molecules has accelerated substantial efforts toward their synthesis.…”

Section: Introductionmentioning

confidence: 99%

π-Expanded Coumarins: One-Pot Photo Synthesis of 5H-Benzo[12,1]tetrapheno[7,6,5-cde]chromen-5-ones and Photophysical Properties

Xue

Wang

et al. 2020

J. Org. Chem.

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The synthesis of a unique type of π-expanded coumarin derivatives, bearing six fused phenyl rings, was achieved via one-pot Suzuki reaction and visible light-driven electrocyclization. The large π-expanded 5H-benzo[12,1]tetrapheno[7,6,5cde]chromen-5-ones were obtained in good to high yields from 1-bromo-2H-phenaleno[1,2,3-de]chromen-2-ones, and the intriguing optical properties were explored by altering the attached functional groups. 2-Arylaminosubstituted-5H-benzo[12,1]tetrapheno-[7,6,5-cde]chromen-5-ones showed a large Stokes shift (4005 cm −1 ) or excellent fluorescence quantum yield (Φ f = 0.75) along with significant bathochromic shift in tetrahydrofuran.

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Photoinduced formation of the laser dye coumarin 6 from its dihydro derivatives

Cited by 27 publications

References 23 publications

Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives

Synthesis and Photophysical Properties of Fluorescent 6-Aryl-D-π-A Coumarin Derivatives

Efficient Synthesis of Fluorescent Coumarins and Phosphorous-Containing Coumarin-Type Heterocycles via Palladium Catalyzed Cross-Coupling Reactions

π-Expanded Coumarins: One-Pot Photo Synthesis of 5H-Benzo[12,1]tetrapheno[7,6,5-cde]chromen-5-ones and Photophysical Properties

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