PHOTOPHYSICAL and PHOTOCHEMICAL PROPERTIES OF COUMARIN DYES IN AMPHIPHILIC MEDIA

Jones, Guilford; Jackson, W. R.; Kanoktanaporn, S.; Bergmark, William R.

doi:10.1111/j.1751-1097.1985.tb01597.x

Cited by 35 publications

(19 citation statements)

References 33 publications

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“…The RFI value of 1f, with the strongest electron-withdrawing nitro group, was comparable with that of 1b, with an electron-donating methyl group. This prominent decrease in 1f may be attributed to the nonemissive twisted ICT (TICT) excited state, [39][40][41][42][43] where push-pull p-electron systems between a methoxyl group at the 6-position and a nitro group at the 3-position in a molecule must be fully separated in polar solvent such as acetonitrile. Rettig and Klock reported that the very weak fluorescence of 6-aminocoumarin with a stronger electron-donating amino group than the methoxyl group was attributed to this TICT between the amino group and coumarin ring.…”

Section: Resultsmentioning

confidence: 99%

Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents

Murata

Masuda

Kamochi

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Fluorometric analysis is one of the most sensitive methods for detecting organic and/or inorganic compounds and therefore it has been widely used in many scientific fields with improving analytical instruments such as high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), fluorescence confocal microscopy, etc. For these purposes, a great deal of effort has gone into the development of fluorescent reagents using various fluorophores, which can be utilized for derivatizing biologically active small molecules, labeling macromolecules such as proteins and DNAs, and probing ions such as biologically relevant metal cations and inorganic or organic anions. [1][2][3][4] In the development of such fluorescent reagents, it should first be ensured that the fluorophore used has a high fluorescence quantum yield because of the reliably high sensitivity in the detection. Fluorescein is one of the most widely used fluorophore for biological experiments, since it has a high fluorescence quantum yield of 0.90 or grater in aqueous solution and its excitation and emission wavelengths are in the visible region. Recently, Nagano and coworkers have succeeded in developing fluorescent reagents for the specific detection of nitric oxide (NO), [5][6][7][8] singlet oxygen ( 1 O 2 ), 9,10) and others 11,12) using fluorescein as the fluorophore. 4,4-Difluoro-4-bora-3a,4a-diazas-indacenes (BODIPYs) are also well-known fluorophores that have very sharp and narrow fluorescence bandwidths in addition to their high fluorescence quantum yield in aqueous solution. 4,13,14) Therefore they have been used as mother fluorophores for many analytical purposes. [15][16][17][18] However, the difference between the excitation and emission wavelengths of these derivatives are very small, less than approximately 30 nm for fluoresceins and 15 nm for BODIPYs, and it is necessary to correct their spectra from interferences such as Rayleigh or Raman scattering light.On the other hand, coumarin (2H-benzopyran-2-one), is also another interesting fluorophore, since its fluorescence changes drastically with substituents and their introduced positions. [19][20][21] In previous papers, we reported the fluorescence characteristics of methoxycoumarins and discussed the structural features of strongly fluorescing methoxycoumarins from the viewpoint of intramolecular charge transfer (ICT) between push-and pull-substituents in the ground and the excited states.22,23) Based on the above findings, we succeeded in developing novel fluorescent reagents with both high sensitivity and functions such as self-catalytic reactivity. [24][25][26] In the course of those studies, we suspected that most coumarin derivatives showed large Stokes shifts in their fluorescence spectra as compared with other fluorophores. These large Stokes shifts appear to be advantageous for escaping autofluorescence from biological molecules and reducing the self-absorption of chromophores. Further, if the emission bands of coumarins could be shifted to longer wavelengths with larg...

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Section: Resultsmentioning

confidence: 99%

Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents

Murata

Masuda

Kamochi

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[1][2][3][4][5][6][7] Aminocoumarin dyes have also been used to study solvation dynamics in zeolites, micelles, and reversed micelles. 8,9 The reason for such a wide application range of the aminocoumarin dyes is due to the fact that on optical excitation they undergo an intramolecular charge transfer (ICT) from the electron-donating amino group to the electron-withdrawing carbonyl group of the coumarin ring.…”

Section: Introductionmentioning

confidence: 99%

Excited-State Behavior of 7-Diethylaminocoumarin Dyes in AOT Reversed Micelles: Size Effects

Raju¹,

Costa²

1999

J. Phys. Chem. B

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Photophysical properties of two 7-diethylaminocoumarin dyes belonging to the family of coumarinylbenzopyrano pyridines (BC I and BC II), and a third dye, 7-diethylamino-4-trifluoromethyl coumarin (C 35), are reported in Aerosol OT (AOT) and water-in-oil (n-heptane/AOT/water) microemulsions. In the case of BC I, emission arising from two different environments for the dye is observed. Results of the steady-state fluorescence anisotropy experiments also support the presence of two different environments. At low W 0 ()[water]/[AOT]) values (0 < W 0 < 10), the excited-state properties of the molecule in the interfacial region are found to be sensitive to the polarity of the surrounding microenvironment. The decrease in the fluorescence quantum yield at higher W 0 (g10) values can be attributed to the intermolecular hydrogen bonding between the cyano (-CN) group of the dye and water molecules present in the micellar interface. These observations are explained on the basis of the comparable size of the probe dye molecule and the molecular dimensions of the interfacial region in the microemulsions. The large molecular size of BC II is also found to be the reason for the sensitivity of the dye to the microenvironment of n-heptane/AOT/water microemulsions. However, the effects are much smaller than those observed in BC I. A similar photophysical study involving C 35 is found to show no such effects. The smaller molecular size, charge neutrality, hydrophobic nature, and a preferential solvation in heptane are essentially the reasons for the results observed in C 35.

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“…In this connection, the following finding is noteworthy. In pursuit of increasing the solubility of coumarins in water, the authors have found that the addition of the pertinent detergents not merely increases the solubility of some of these dyes by orders of magnitude but also causes spectral shifts in the coumarins fluorescence (up to 30 nm), enhance their fluorescence quantum yield and reluctance towards photodegradation. In the context of the present work, noteworthy is also more apposite way to modify the spectral characteristics of organic dyes in both liquid and solid environments, which pertains to using the structured media …”

Section: Introductionmentioning

confidence: 99%

Exploring the utility of coumarins‐based luminescent spectra converters

Lapina

Павич

Першукевич

et al. 2017

J of Physical Organic Chem

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The physicochemical aspects of functioning the luminescent converters for a rational modification of the emission spectra of light-emitting diodes are considered. These converters use laser dyes' coumarins 314, 334, and 343 to transfigure the primary light-emitting diode spectrum. The fine control of the emission spectra of the mentioned coumarins in polymeric matrices was achieved by introducing nonionic detergents. The relevant characteristics of the photochemical persistence of coumarins in the polymer layers are acquired.

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PHOTOPHYSICAL and PHOTOCHEMICAL PROPERTIES OF COUMARIN DYES IN AMPHIPHILIC MEDIA

Cited by 35 publications

References 33 publications

Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents

Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents

Excited-State Behavior of 7-Diethylaminocoumarin Dyes in AOT Reversed Micelles: Size Effects

Exploring the utility of coumarins‐based luminescent spectra converters

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