Physicochemical studies of molecular hyperpolarizability of imidazole derivatives

Jayabharathi, Jayaraman; Thanikachalam, Venugopal; Srinivasan, N.; Perumal, Marimuthu Venkatesh; Jayamoorthy, K.

doi:10.1016/j.saa.2011.02.024

Cited by 39 publications

(9 citation statements)

References 33 publications

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“…The geometry of all involved structures was fully optimized with the DFT method, using B3LYP/6‐31G (d,p) basis set. The density functional theory was used to calculate the dipole moment ( μ ), mean polarizability ( α ), and the total first static hyperpolarizability ( β ) of these phenanthrimidazole derivatives in terms of x , y , and z components using the following equations:

μ = {()(, μ^{2}_{x} + μ^{2}_{y} + μ^{2}_{z})}^{\frac{1}{2}}; α = 1 / 3 (α_{italicxx}_{+} α_{yy +} αzz); β_{normaltot} = {()(, β_{x}^{2} + β_{y}^{2} + β_{z}^{2})}^{1 / 2}

β_{normaltot} = {(][, {(β_{italicxxx} + β_{italicxyy} + β_{italicxzz})}^{2} + {(β_{italicyyy} + β_{italicyzz} + β_{italicyxx})}^{2} + {(β_{italiczzz} + β_{italiczxx} + β_{italiczyy})}^{2})}^{1 / 2}

…”

Section: Methodsmentioning

confidence: 99%

“…= 8.3693 × 10 −33 e.s.u.). The second order Fock matrix was carried out to evaluate the donor–acceptor interactions in the natural bond orbital (NBO) analysis . For each donor (i) and acceptor (j), the stabilization energy E (2) associated with the delocalization i → j is estimated as, E (2) = q i

\frac{{F (normali, normalj)}^{2}}{italicεj - italicεi}

, where q i is the donor orbital occupancy, ε i and ε j are diagonal elements, and F(i, j) is the off diagonal NBO Fock matrix element.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Electronic properties of phenanthrimidazoles as hole transport materials in organic light emitting devices and in photoelectron transfer to ZnO nanoparticles

Karunakaran

Jayabharathi

Perumal

et al. 2013

J. Phys. Org. Chem.

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Phenanthrimidazoles as hole transport materials have been synthesized, characterized, and applied as nondoping emitters in organic light emitting devices. The synthesized molecules possess high fluorescent quantum yield and thermal properties and display film forming abilities. The highest occupied molecular orbital (HOMO) energies of these materials are shallower than the reported tris(8-hydroxyquinoline)aluminum (Alq 3 ), which enables the hole transport ability of these phenanthrimidazoles. Taking advantage of the thermal stability and hole transporting ability, these compounds can be used as a functional layer between NPB [4,4-bis(N-(1-naphthyl)-N-phenylamino)biphenyl] and Alq 3 layers and show that these phenanthrimidazoles can be alternatively used as novel hole transport materials and to improve the device performances. Geometrical, optical, electrical, and electroluminescent properties of these molecules have been probed. Further, natural bond orbital, nonlinear optical materials (NLO), molecular electrostatic potential, and HOMO-lowest unoccupied molecular orbital (LMO) energy analysis have been made by density functional theory (DFT) method to support the experimental results. Hyperpolarizability analysis reveals that the synthesized phenanthrimidazoles possess NLO behavior. The chemical potential, hardness, and electrophilicity index of phenanthrimidazoles have also been computed by DFT method. Photoinduced electron transfer explains the enhancement of fluorescence by nanoparticulate ZnO, and the apparent binding constant has been obtained. Adsorption of the fluorophore on ZnO nanoparticle lowers the HOMO and LUMO energy levels of the fluorophore. The strong adsorption of the phenanthrimidazoles on the surface of ZnO nanocrystals is likely due to the chemical affinity of the nitrogen atom of the organic molecule to Zn(II) on the surface of nanocrystal.To zinc acetate (0.1 g) solution under continuous stirring, aqueous ammonia (1:1) was added dropwise to reach a pH of 7, and the stirring was continued for another 30 min. The formed glassy-like white gel was allowed to age overnight. It was filtered, washed with water and ethanol, dried at 100 C for 12 h, calcinated at 500 C for 2 h [69] at a heating rate 10 C min À1 .

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μ = {()(, μ^{2}_{x} + μ^{2}_{y} + μ^{2}_{z})}^{\frac{1}{2}}; α = 1 / 3 (α_{italicxx}_{+} α_{yy +} αzz); β_{normaltot} = {()(, β_{x}^{2} + β_{y}^{2} + β_{z}^{2})}^{1 / 2}

β_{normaltot} = {(][, {(β_{italicxxx} + β_{italicxyy} + β_{italicxzz})}^{2} + {(β_{italicyyy} + β_{italicyzz} + β_{italicyxx})}^{2} + {(β_{italiczzz} + β_{italiczxx} + β_{italiczyy})}^{2})}^{1 / 2}

…”

Section: Methodsmentioning

confidence: 99%

\frac{{F (normali, normalj)}^{2}}{italicεj - italicεi}

, where q i is the donor orbital occupancy, ε i and ε j are diagonal elements, and F(i, j) is the off diagonal NBO Fock matrix element.…”

Section: Methodsmentioning

confidence: 99%

Electronic properties of phenanthrimidazoles as hole transport materials in organic light emitting devices and in photoelectron transfer to ZnO nanoparticles

Karunakaran

Jayabharathi

Perumal

et al. 2013

J. Phys. Org. Chem.

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“…The electric dipole moment ( μ ), polarisability ( α ) and the first order hyperpolarizability ( β ) values shows the investigated molecule (FKDTA) become NLO active by using Gaussian 09 package with B3LYP/6‐31+G(d,p) model. The FKDTA possess a more appropriate ratio of off diagonal versus diagonal β tensorial component (r) with a magnitude of 0.01which reflects the in‐plane nonlinearity anisotropy . First order hyperpolarizability is a third rank tensor of β reduced to 10 components due to the Kleinman symmetry .…”

Section: Resultsmentioning

confidence: 99%

In Silico Quantum Chemical and Crystallographic Treatment of α‐Formylketene Dithioacetal towards the Elucidation of Its Structural and Optical Nature

et al. 2016

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a-Formylketene dithioacetal is a vital precursor for the synthesis of a number of heterocyclic compounds including isoxazoles, pyrimidines, naphthyridines, pyridones, nicotinonitriles and its functionalized materials. Apart from the synthetic applications, the crystalline and non linear optical nature is also considerable, hence the present study deals with the structural and hyperpolarizability aspects of a representative compound from the family of a-formylketene dithioacetal, 2-(4-methoxybenzoyl)-3,3-bis(methylsulfanyl)prop-2-enal (FKDTA), was synthesized with a reported protocol and characterized. The complete three dimensional solid state structural studies were carried out utilizing single crystal X-ray crystallographic technique along with Hirshfeld surfaces followed by various quantum chemical parameters were performed including non-linear optical effects and it is discussed to reveals the complete structural peculiarities towards the optical behaviours of the designated compound.

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“…For instance, phenolphthalein changes from colorless to a pale pink colored substance when altering pH of the medium. The main halochromic compounds classes are: phthalides, [6] coumarin, [7] azo dyes, [8] and Imidazole derivatives [9,10] etc., In particular, the imidazole derivatives have been shown as impressive fluorophores due to their larger π-conjugated structure and acidity nature of the NH-group. These optical properties have been exploited in different applications like photographic materials, luminescent materials, two-photon absorption applications, two-photon fluorescence microscopy, high density storage and 3D microfabrication, Non Linear Optics (NLO), Dye Sensitized Solar Cells (DSSC), Organic Light Emitting Diodes (OLEDs) and molecular switches, etc., [11][12][13] The well-known 4-(4,5-diphenyl-1H-imidazol-2-yl)benzaldehyde (DPI-BA) ( Figure 1) has been condensed with various functional groups to make a different push-pull chromophore motifs such as D-π-A, D-π-D or A'-π-A, Y-shaped so on.…”

Section: Introductionmentioning

confidence: 99%

¹H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis

et al. 2020

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In the present study the molecular structure of compound 4‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde [DPI‐BA] and its optoelectronic properties are reported. The SCXRD analysis revealed that DPI‐BA crystallizes in the Orthorhombic crystal system and Pca21 space group with Z=4. The intermolecular N‐H⋅⋅N interaction generates a one‐dimensional chain. An interesting halochromic behavior was observed for the DPI‐BA in THF:H2O (9:1) by varying the pH analysis. The fluorescence properties of neutral and acid‐base solutions were monitored by UV‐vis and 1D, 2D‐NMR studies. The HCl vapor was bubbled to the DPI‐BA in the DMSO‐d6 solution and the corresponding fluorescence wavelength changed from green (λem 501 nm) to blue (λem 459 nm). In the case of a basic pH solution was made by adding NaOH flakes to the DPI‐BA DMSO‐d6 solution and then the fluorescence wavelength changed from green to orange (λem 595 nm). The λmax of PL emission could be correlated to intermolecular charge transfer (ICT). The optical absorption and cyclic voltammetry measurement were performed to determine the bandgap. Besides, the quantitative analysis of intermolecular interactions through PIXEL, QTAIM, NBO, GIAO‐DFT methods and DFT studies was correlated to the experiments.

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Physicochemical studies of molecular hyperpolarizability of imidazole derivatives

Cited by 39 publications

References 33 publications

Electronic properties of phenanthrimidazoles as hole transport materials in organic light emitting devices and in photoelectron transfer to ZnO nanoparticles

Electronic properties of phenanthrimidazoles as hole transport materials in organic light emitting devices and in photoelectron transfer to ZnO nanoparticles

In Silico Quantum Chemical and Crystallographic Treatment of α‐Formylketene Dithioacetal towards the Elucidation of Its Structural and Optical Nature

¹H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis

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Physicochemical studies of molecular hyperpolarizability of imidazole derivatives

Cited by 39 publications

References 33 publications

Electronic properties of phenanthrimidazoles as hole transport materials in organic light emitting devices and in photoelectron transfer to ZnO nanoparticles

Electronic properties of phenanthrimidazoles as hole transport materials in organic light emitting devices and in photoelectron transfer to ZnO nanoparticles

In Silico Quantum Chemical and Crystallographic Treatment of α‐Formylketene Dithioacetal towards the Elucidation of Its Structural and Optical Nature

1H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis

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¹H‐NMR, Photophysical, and pH Studies of 4‐(4,5‐Diphenyl‐1H‐imidazol‐2‐yl)benzaldehyde through Experimental and DFT Theoretical Analysis