Hydrogen-bonding effect on the photophysical properties of 7-aminocoumarin derivatives

Arbeloa, Teresa; Arbeloa, F. López; Tapia, María J.; Arbeloa, Í. López

doi:10.1021/j100120a024

Cited by 174 publications

(209 citation statements)

References 3 publications

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“…The standard deviations of the spectra are good indices for the bandwidth of the spectra. The peak of the fluorescence spectrum of Model I and the constructed absorption spectra agrees well with the experimental spectra observed by Arbeloa et al [47]. This shows the accuracy of our calculation scheme.…”

Section: The Steady-state Fluorescence Spectra and Solvent Effectsupporting

confidence: 89%

Solvent Effect on the Fluorescence Spectra of Coumarin 120 in Water: A Combined Quantum Mechanical and Molecular Mechanical Study

et al. 2012

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The solvent effect on the steady-state and time-resolved fluorescence spectra of coumarin 120 in water was studied utilizing a molecular dynamics simulation with combined quantum mechanical/molecular mechanical method. The constructed steady-state fluorescence spectra reproduced the Stokes shift of the experimental data. The solvent effects on the spectra were examined by constructing three different spectra: spectra using the entire system, spectra including water molecules only in the first solvent shell, and spectra excluding all water molecules. We found that the variation in C-C bond length makes the largest contribution to the solvent shift in the fluorescence spectrum, which indicates the importance of the electronic structure variation.

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Section: The Steady-state Fluorescence Spectra and Solvent Effectsupporting

confidence: 89%

Solvent Effect on the Fluorescence Spectra of Coumarin 120 in Water: A Combined Quantum Mechanical and Molecular Mechanical Study

et al. 2012

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“…[14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29] These dyes can form HBs with solvents in the ground and the excited states. [14][15][16][17][18][19][20][21][22][23][24][25][26]29] Coumarin 120 (C120, 7-amino-4-methylbenzopyrone; see Figure 1) forms three types of HBs (Figure 2), with participation of the amino nitrogen atom (type A), carbonyl oxygen atom (type B), and an amino hydrogen atom (type C). [14][15][16][17] The number and types of HBs formed are solvent-dependent; some solvents can form three types of HB with C120, while others only form one or two.…”

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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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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“…Several experimental studies using time-resolved emission methods, such as fluorescence spectroscopy [6][7][8][9][10][11][12][13] or UV photoelectron spectroscopy 14 , have permitted to measure and resolve in time the emission redshift for solvents of different polarity. In particular, Gustavsson and coworkers have given a description of the fluorescence spectra on the femtosecond time scale 8 .…”

Section: Introductionmentioning

confidence: 99%

A hybrid TDDFT/MM investigation of the optical properties of aminocoumarins in water and acetonitrile solution

Sulpizi

Carloni

Hutter

et al. 2003

Phys. Chem. Chem. Phys.

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A hybrid TDDFT/MM investigation of the optical properties of aminocoumarins in water and acetonitrile solution Sulpizi, M; Carloni, P; Hutter, J; Röthlisberger, U AbstractWe present a hybrid Time-Dependent Density Functional /Molecular Mechanics (TDDFT/MM) simulation study on the optical properties of aminocoumarins in gas phase and solution. As solvation is described through a molecular approach, the effects due to the inhomogeneities of the electric field of the solvent molecules are fully included. We focus on the ground state and first excited singlet state properties of C151, C35 and C153, three aminocoumarins for which a homogeneous set of experimental data is available.Our approach is able to give quantitative information on the redshifts in water and acetonitrile, two solvents which show different H-bonding properties. In addition, it is able to quantify the effects of chemical substituents, such as the spectral redshift due to the increased alkylation at the amino position.

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Hydrogen-bonding effect on the photophysical properties of 7-aminocoumarin derivatives

Cited by 174 publications

References 3 publications

Solvent Effect on the Fluorescence Spectra of Coumarin 120 in Water: A Combined Quantum Mechanical and Molecular Mechanical Study

Solvent Effect on the Fluorescence Spectra of Coumarin 120 in Water: A Combined Quantum Mechanical and Molecular Mechanical Study

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

A hybrid TDDFT/MM investigation of the optical properties of aminocoumarins in water and acetonitrile solution

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