Photophysical Properties of (Dimethylamino)anthraquinones: Radiationless Transitions in Solvent and Polyelectrolyte Media

Jones, Guilford; Feng, Zhiming; Bergmark, William R.

doi:10.1021/j100068a007

Cited by 41 publications

(51 citation statements)

References 3 publications

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“…Water molecules can form type A, B, and C HBs, and it may be necessary to include the four water molecules closest to C120. Our calculations indicate that four water molecules can coexist in a stable C120-(H 2 O) 4 complex having one type A, one type B, and two type C HBs, and the calculated absorption wavelength of 340.02 nm for this complex is quite close to the experimental value (342 nm). [29] The above results suggest that the interplay of three types of HBs with four water molecules controls the absorption maximum, and the C120-(H 2 O) 4 complex may be a probable scenario in aqueous solution.…”

Section: Absorption Spectra Of C120 Hb Complexes In Various Solventssupporting

confidence: 75%

“…[1][2] The fluorescence quantum yield of 7-aminocoumarins is usually very high, and the absorption and emission maxima are very sensitive to solvent polarity. [3][4][5][6][7][8][9][10][11][12] They also show Stokes shifts that are strongly dependent on polarity [12] and large changes in dipole moment on excitation. [13] Due to these interesting properties, the 7-aminocoumarins have been widely used as probes in studying solvatochromic properties and diverse characteristics of the solute-solvent interaction.…”

Section: Introductionmentioning

confidence: 99%

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Influence of Solvent Polarity and Hydrogen Bonding on the Electronic Transition of Coumarin 120: A TDDFT Study

et al. 2008

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The characteristics of the electronic transition energy of Coumarin 120 (C120) and its H-bonded complexes in various solvents have been examined by time-dependent density functional theory (TDDFT) in combination with a polarizable continuum solvent model (PCM). Molecular structures of C120 and its H-bonded complexes are optimized with the B3LYP method in PCM solution, and the dihedral angle H14-N13-C7-H15 is dependent on solvent polarity and the type of H-bond. A linear correlation of the absorption maximum of C120 with the solvent polarity function is revealed with the PCM model for all solvents except DMSO. The experimental absorption maximum of C120 in nine solvents is well described by a PCM-TDDFT scheme augmented with explicit inclusion of a few H-bonded solvent molecules, and quantitative agreement between our calculated results and experimental measurements is obtained with an average error of less than 2 nm. H-bonding at three different sites shifts the absorption wavelength of C120 either to the blue or to the red, that is, a significant role is played by solvent molecules in the first solvation shell in determining the electronic transition energy of C120. The dependence on the H-bonding site and solvent polarity is examined by using the Kamlet-Taft equation for solvatochromism.

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Section: Absorption Spectra Of C120 Hb Complexes In Various Solventssupporting

confidence: 75%

Section: Introductionmentioning

confidence: 99%

Influence of Solvent Polarity and Hydrogen Bonding on the Electronic Transition of Coumarin 120: A TDDFT Study

et al. 2008

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“…Among these dyes, those having different amino groups at position 7 (commonly known as 7-aminocoumarins) are of special significance [1][2][3][4][5][6][7][8][9][10][11][12][13]. The fluorescence quantum yield (f f ) of these dyes is usually very high, often close to unity [1][2][3][4][5][6][7][8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…The fluorescence quantum yield (f f ) of these dyes is usually very high, often close to unity [1][2][3][4][5][6][7][8][9][10][11][12][13]. These dyes undergo substantial changes in their dipole moment on excitation, causing large Stokes shifts between their absorption and fluorescence spectra [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. These Stocks' shifts are again very sensitive to solvent polarities [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

“…These dyes undergo substantial changes in their dipole moment on excitation, causing large Stokes shifts between their absorption and fluorescence spectra [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. These Stocks' shifts are again very sensitive to solvent polarities [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. Because of these properties, the 7-aminocoumarin dyes have widely been used as probes in a variety of investigation, i.e., in the study of solvatochromic properties [9][10][11][12][13], determination of polarities in microenvironments [14,15], and measurements of solvent relaxation times [16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

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Photophysical parameters and fluorescence quenching of 7-diethylaminocoumarin (DEAC) laser dye

El-Mossalamy

Obaid

El‐Daly

2011

Optics & Laser Technology

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An Isothiazolanthrone‐Based Self‐Assembling Anticancer Color‐Changing Dye for Concurrent Imaging and Monitoring of Cell Viability

Gour

Kshtriya

Khatun

et al. 2023

Chemistry An Asian Journal

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We report the photophysical properties, self‐assembly and biological evaluation of an isothiazolanthrone‐based dye, 7‐amino‐6H‐anthra[9,1‐cd]isothiazol‐6‐one (AAT), which reveals anticancer properties and can be potentially used as dye for monitoring cell viability. The solvent‐dependent photophysical studies suggest that the emission of AAT is sensitive to environment polarity due to which interesting changes in the colored emission may be observed owing to the charge transfer (CT) processes. AAT also self‐assembles to tree‐like branched morphologies and produce, a greenish emission inside the cells when imaged after short interval (15 mins) of incubation while a red fluorescence could be noted after 24 h. Interestingly, AAT also produce differential emission inside mouse normal cells as compared to its cancer cell lines since it possess anticancer activity. The experimental observations were also validated theoretically via computational modeling.

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Photophysical Properties of (Dimethylamino)anthraquinones: Radiationless Transitions in Solvent and Polyelectrolyte Media

Cited by 41 publications

References 3 publications

Influence of Solvent Polarity and Hydrogen Bonding on the Electronic Transition of Coumarin 120: A TDDFT Study

Influence of Solvent Polarity and Hydrogen Bonding on the Electronic Transition of Coumarin 120: A TDDFT Study

Photophysical parameters and fluorescence quenching of 7-diethylaminocoumarin (DEAC) laser dye

An Isothiazolanthrone‐Based Self‐Assembling Anticancer Color‐Changing Dye for Concurrent Imaging and Monitoring of Cell Viability

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