Water-soluble coumarin dyes for flashlamp-pumped dye lasers

Drexhage, K. H.; Erikson, G. R.; Hawks, G.H.; Reynolds, G. A.

doi:10.1016/0030-4018(75)90255-2

Cited by 60 publications

(26 citation statements)

References 16 publications

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“…Acid 7 a,COOH was prepared from ester 7 a,COOEt (Scheme 1) according to the known method. [3f] Reduction of the acid chloride (prepared from 7 a,COOH and oxalyl or thionyl chloride) with hydrogen over the Lindlar catalyst failed to produce aldehyde 3, but we were able to detect the formation of aldehyde 3 by using LiAlHA C H T U N G T R E N N U N G (OBut) 3 . However, we failed to isolate compound 3 in a pure state or to condense it in situ with N-methylpyridinium salts.…”

Section: Resultsmentioning

confidence: 98%

“…[2] Various classes of dyes have been used for staining and bioimaging, and coumarins are quite prominent among them. Coumarins have a long history as laser dyes, [3] and nowadays they are widely used as fluorescent chemosensors and labels for proteins, nucleic acids, lipids, carbohydrates, toxins, hormones, and other biomolecules. [4,5] The parent compound at room temperature shows no fluorescence and only a weak absorption at 312 nm with e = 5370 dm 3 mol À1 cm À1 .…”

Section: Introductionmentioning

confidence: 99%

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4‐Trifluoromethyl‐Substituted Coumarins with Large Stokes Shifts: Synthesis, Bioconjugates, and Their Use in Super‐Resolution Fluorescence Microscopy

Schill

Nizamov

Bottanelli

et al. 2013

Chemistry A European J

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Bright and photostable fluorescent dyes with large Stokes shifts are widely used as sensors, molecular probes, and light-emitting markers in chemistry, life sciences, and optical microscopy. In this study, new 7-dialkylamino-4-trifluoromethylcoumarins have been designed for use in bioconjugation reactions and optical microscopy. Their synthesis was based on the Stille reaction of 3-chloro-4-trifluoromethylcoumarins and available (hetero)aryl- or (hetero)arylethenyltin derivatives. Alternatively, the acylation of 2-trifluoroacetyl-5-dialkylaminophenols with available (hetero)aryl- or (hetero)arylethenylacetic acids followed by intramolecular condensation afforded coumarins with 3-(hetero)aryl or 3-[2-(hetero)aryl]ethenyl groups. Hydrophilic properties were provided by the introduction of a sulfonic acid residue or by phosphorylation of a primary hydroxy group attached at C-4 of the 2,2,4-trimethyl-1,2-dihydroquinoline fragment fused to the coumarin fluorophore. For use in immunolabeling procedures, the dyes were decorated with an (activated) carboxy group. The positions of the absorption and emission maxima vary in the ranges 413-480 and 527-668 nm, respectively. The phosphorylated dye, 9,CH=CH-2-py,H, with the 1-(3-carboxypropyl)-4-hydroxymethyl-2,2-dimethyl-1,2-dihydroquinoline fragment fused to the coumarin fluorophore bearing the 3-[2-(2-pyridyl)ethenyl] residue (absorption and emission maxima at 472 and 623 nm, respectively) was used in super-resolution light microscopy with stimulated emission depletion and provided an optical resolution better than 70 nm with a low background signal. As a result of their large Stokes shifts, good fluorescence quantum yields, and adequate photostabilities, phosphorylated coumarins enable two-color imaging (using several excitation sources and a single depletion laser) to be combined with subdiffractional optical resolution.

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Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

4‐Trifluoromethyl‐Substituted Coumarins with Large Stokes Shifts: Synthesis, Bioconjugates, and Their Use in Super‐Resolution Fluorescence Microscopy

Schill

Nizamov

Bottanelli

et al. 2013

Chemistry A European J

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“…The 7-amino coumarin dye molecules (such as Coumarin 1, Coumarin 6, Coumarin 120, and Coumarin 343) have strong absorption and emission in the blue and green regions of the spectra. 4,5 They thus become ideal candidates as dye photosensitizers. [6][7][8][9][10][11] In addition, these dye molecules have other applications in laser dyes, 4, 5 solvation and fluorescence probe molecules.…”

Section: Introductionmentioning

confidence: 99%

“…Meanwhile, experimental measurements show that the absorption and emission spectra of C343 strongly depend on the solvent polarity, the H-bond donation and acceptance abilities. 5,14,15,[24][25][26][27][28][29] Especially, the different pH values of the solution may significantly change spectral properties. 12,21,28,30,31 For instance, C343 in basic solution a) Author to whom correspondence should be addressed.…”

Section: Introductionmentioning

confidence: 99%

Theoretical studies on absorption, emission, and resonance Raman spectra of Coumarin 343 isomers

Cao

Zhao

2012

The Journal of Chemical Physics

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The vibrationally resolved spectral method and quantum chemical calculations are employed to reveal the structural and spectral properties of Coumarin 343 (C343), an ideal candidate for organic dye photosensitizers, in vacuum and solution. The results manifest that the ground-state energies are dominantly determined by different placements of hydrogen atom in carboxylic group of C343 conformations. Compared to those in vacuum, the electronic absorption spectra in methanol solvent show a hyperchromic property together with the redshift and blueshift for the neutral C343 isomers and their deprotonated anions, respectively. From the absorption, emission, and resonance Raman spectra, it is found that the maximal absorption and emission come from low-frequency modes whereas the high-frequency modes have high Raman activities. The detailed spectra are further analyzed for the identification of the conformers and understanding the potential charge transfer mechanism in their photovoltaic applications.

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“…Coumarins [2], azacoumarins [3] and chinolones [4] are well known fluorescent dyes with a molecular shape and size similar to naphthyridines but differing in their capabilities to form hydrogen bonds. The dialkylamino substituted 4-methyl-[1.8] naphthyridines described here are new and stable compounds that can be obtained easily through a synthesis consisting of only a few steps, and show an interesting fluorescence behaviour.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent 2,7-Dialkylamino-[1,8]-Naphthyridines: Preparation and Spectroscopic Properties

Hoock

Reichert²,

Schmidtke³

1999

Molecules

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Water-soluble coumarin dyes for flashlamp-pumped dye lasers

Cited by 60 publications

References 16 publications

4‐Trifluoromethyl‐Substituted Coumarins with Large Stokes Shifts: Synthesis, Bioconjugates, and Their Use in Super‐Resolution Fluorescence Microscopy

4‐Trifluoromethyl‐Substituted Coumarins with Large Stokes Shifts: Synthesis, Bioconjugates, and Their Use in Super‐Resolution Fluorescence Microscopy

Theoretical studies on absorption, emission, and resonance Raman spectra of Coumarin 343 isomers

Fluorescent 2,7-Dialkylamino-[1,8]-Naphthyridines: Preparation and Spectroscopic Properties

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