DFT/TDDFT study on the electronic structure and spectral properties in annulated analogue of phenyl heteroazulene derivative

̧siorski, P. Ga; Danel, Krzysztof; Matusiewicz, Małgorzata; Uchacz, Tomasz; Kuźnik, W.; ̧tek, Ł. Pia; Kityk, A. V.

doi:10.1016/j.matchemphys.2011.11.025

Cited by 30 publications

(8 citation statements)

References 36 publications

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“…However, to obtain the best agreement between the theoretically predicted and experimentally derived values, use of different functionals and basis sets can be important. Several examples supporting this notion can be found in literature …”

Section: Introductionsupporting

confidence: 63%

Electronic structure and spectroscopic properties of 6‐aminophenanthridine and its derivatives: Insights from density functional theory

Vovusha

Banerjee

Oumata

et al. 2015

Int J of Quantum Chemistry

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a] 6-Aminophenanthridine (6AP) and its derivatives show important biological activities as antiprion compounds and inhibitors of the protein folding activity of the ribosome. Both of these activities depend on the RNA binding property of these compounds, which has been recently characterized by fluorescence spectroscopy. Hence, fundamental insights into the photophysical properties of 6AP compounds are highly important to understand their biological activities. In this work, we have calculated electronic structures and optical properties of 6AP and its three derivatives 6AP8CF 3 , 6AP8Cl, and 6APi by density functional theory (DFT) and time-dependent density functional theory (TDDFT). Our calculated spectra show a good agreement with the experimental absorption and fluorescence spectra, and thus, provide deep insights into the optical properties of the compounds. Furthermore, comparing the results obtained with four different hybrid functionals, we demonstrate that the accuracy of the functionals varies in the order B3LYP > PBE0 > M062X > M06HF.

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Section: Introductionsupporting

confidence: 63%

Electronic structure and spectroscopic properties of 6‐aminophenanthridine and its derivatives: Insights from density functional theory

Vovusha

Banerjee

Oumata

et al. 2015

Int J of Quantum Chemistry

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“…The transferability of the μ value for prediction of the absorption spectra in the nonpolar and polar solvents is also tested because their absorption spectra are independent of solvent types. [1][2][3]18,19,25 Also, the conformational search of the compounds was also performed to examine the conformational effects on the spectroscopic properties. The spectra, electronic transition, and molecular orbitals (MOs) were analyzed and compared with the experiments.…”

Section: Introductionmentioning

confidence: 99%

“…However, the results from TD-DFT of those compounds using the popular B3LYP functional in the gas phase could differ from the data calculated in the implicit solvent and different DFT functionals. Lately, there are some reports indicating that the TD-B3LYP method can be used to simulate the spectra of basic and small compounds, but TD-B3LYP cannot be applied for medium-sized compounds. ,,− In contrast, some long-range (LC) corrected functions could give better agreement results with the experiments. ,− ,− Moreover, the LC-BLYP functional has been applied to simulate the absorption and emission spectra of some small- and medium-sized organic dyes and fluorophores inheriting the ICT character. ,,,− This seems that LC-BLYP may be suitable for the TD-DFT calculations of the fluorophores, although the adjustable damping parameter (μ) is its drawback. ,, The theory of LC is not described here since the LC method introduced initially by Seminario and Gill was developed and reported and the tuning of the μ value used for the two-electron repulsion operator was described elsewhere. ,,,,− …”

Section: Introductionmentioning

confidence: 99%

“…Adjustment of the μ value of LC-BLYP for the prediction of the absorption and fluorescence emission of each compound in each solvent was tested and compared with the experimental data to find the optimal μ value. The transferability of the μ value for prediction of the absorption spectra in the nonpolar and polar solvents is also tested because their absorption spectra are independent of solvent types. − ,,, Also, the conformational search of the compounds was also performed to examine the conformational effects on the spectroscopic properties. The spectra, electronic transition, and molecular orbitals (MOs) were analyzed and compared with the experiments.…”

Section: Introductionmentioning

confidence: 99%

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LC-BLYP Calculations of the Structures and Photophysical Properties of [1,3]Thiazolo[4,5-b]pyrazine Derivatives in Cyclohexane and Methanol

Dokmaisrijan

Kungwan

2019

J. Phys. Chem. A

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Applications of the B3LYP and LC-BLYP functionals with the 6-311+G(d,p) basis set for predicting absorption and fluorescence spectra of benzothiazole and 11 [1,3]thiazolo[4,5-b]pyrazine (TPy) derivatives in implicit solvents (cyclohexane and methanol) were tested and compared with experimental results. The damping parameter of LC-BLYP was tuned for simulating absorption and fluorescence spectra of each compound. For the 11 TPy derivatives, four and seven compounds are small- and medium-sized TPy derivatives, respectively. From this calculation, TD-B3LYP can be used to simulate the absorption spectra of the small-sized compounds in cyclohexane and methanol, but it gives poor results for the fluorescence spectra in cyclohexane and methanol. Contrarily, the LC-BLYP functional with the optimal damping parameter can reproduce the absorption and fluorescence spectra of all compounds in cyclohexane and methanol. The values of the damping parameter of LC-BLYP depend on the types of substituents and solvents. Moreover, the conformations of the compounds do not affect the spectra, and the molecular size and molecular dipole moment do not affect the damping parameter. In addition, types and the number of substitutions attached to the phenyl rings of TPy as well as solvent polarity play the key roles in the long-wavelength fluorescence emission and fluorescence brightness of the compounds. The intramolecular charge transfer of the compounds containing the −NMe2 and −CN groups is predominant in methanol, resulting in a large Stokes shift and oscillator strength.

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“…9 It is currently well established that time-dependent density functional theory (TDDFT) 10 can provide an accurate description of the physical and chemical properties of excited states. [11][12][13][14][15][16][17] Compared to the sophisticated post-Hartree-Fock approaches, TDDFT is the best compromise between accuracy and computational cost.…”

Section: Introductionmentioning

confidence: 99%

State-Specific (Linear-Response)-Polarizable Continuum Models/ Time-Dependent Density Functional Theory Study on the Absorption and Emission Spectra of an Organic Fluorescent Emitter

刘小君¹,

林涛²,

蔡新晨³

et al. 2012

Acta Physico-Chimica Sinica

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3-(dicyanomethylene)-5,5-dimethyl-1-(3-[9-(2-ethyl-hexyl)-carbazol]-vinyl) cyclohexene (DCDHCC) is one of a series of organic dyes with good emission performance in photoelectric devices. The absorption and emission spectra of DCDHCC were computed using PBE0, BMK, and M06 hybrids in the frame of time-dependent density functional theory (TDDFT) in combination with polarizable continuum models (PCMs). Linear-response (LR) and state-specific (SS) PCM approaches were used as well as 6-31G(d) and 6-31+G(d,p) basis sets. The absorption and emission spectra were calculated in benzene, tetrahydrofuran, and acetone and compared with experimental observations. On the one hand, choice of hybrids was found to have a greater effect on the absorption spectra than the basis sets or the solvent model and BMK was established to be a [Article] www.whxb.pku.edu.cn

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DFT/TDDFT study on the electronic structure and spectral properties in annulated analogue of phenyl heteroazulene derivative

Cited by 30 publications

References 36 publications

Electronic structure and spectroscopic properties of 6‐aminophenanthridine and its derivatives: Insights from density functional theory

Electronic structure and spectroscopic properties of 6‐aminophenanthridine and its derivatives: Insights from density functional theory

LC-BLYP Calculations of the Structures and Photophysical Properties of [1,3]Thiazolo[4,5-b]pyrazine Derivatives in Cyclohexane and Methanol

State-Specific (Linear-Response)-Polarizable Continuum Models/ Time-Dependent Density Functional Theory Study on the Absorption and Emission Spectra of an Organic Fluorescent Emitter

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