DFT-TDDFT framework of diphenylamine based mixed valence compounds for optoelectronic applications – Structural modification of π-acceptors

Bella, Antony Paulraj; Panneerselvam, Murugesan; Vedha, Swaminathan Angeline; Jaccob, Madhavan; Solomon, Rajadurai Vijay; Merlin, J. Princy

doi:10.1016/j.commatsci.2019.02.014

Cited by 14 publications

(12 citation statements)

References 64 publications

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“…A rr-HT-P3HT crystalline structure consists of chains of adjacent thiophene rings slightly rotated with respect to each other around the polythiophene backbone axis. Bella et al [8] used TD-DFT with functional B3LYP, basis set 6-31G(d) to evaluate the optoelectronic properties of diphenylamine in conjugation with biphenyl-based π acceptors, such as bifuran, bithiophene, and bipyrrole. Their results indicated that relative to other heteroaromatic π-acceptors, bithiophene-substituted molecules had the highest lowest unoccupied molecular orbital (LUMO) contribution and thus exhibited a higher absorption, higher emission λmax, and lower highest occupied molecular orbital (HOMO)-LUMO gap.…”

Section: Introductionmentioning

confidence: 99%

Electronic and Optical Properties of Polythiophene Molecules and Derivatives

et al. 2021

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The electronic and optical properties of polythiophene (PT) for polymer light-emitting diodes (PLEDs) were calculated using density functional theory (DFT) and time-dependent DFT. We calculated the electronic and optical properties of thiophene and PT polymers with degrees of polymerization (DP) from 2 to 30 monomers (T1–T30) and their derivatives. The associated highest occupied molecular orbital (HOMO) energy, lowest unoccupied molecular orbital (LUMO) energy, band gaps, electron orbitals, and molecular structures were determined. As the DP increased, the LUMO energy gradually decreased, and the HOMO energy gradually increased. The band gap of PT approached 2 eV as the DP of the PT polymer increased from 1 to 30. The calculations and exchange–correlation functional were verified against values in the literature and experimental data from cyclic voltammetry (redox potential) and ultraviolet-visible, photoluminescence, and ultraviolet photoelectron spectra. The color of PT PLEDs can be adjusted by controlling the DP of the polymer and the substituents.

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Section: Introductionmentioning

confidence: 99%

Electronic and Optical Properties of Polythiophene Molecules and Derivatives

et al. 2021

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“…The desired product was detected in the crude reaction mixture by GC/MS but all attempted isolations failed. EI-MS (70 eV): m/z (%): 344 (M + ,100), 311 (97), 287 (69), 255 (20), 172 (20), 102 (18).…”

Section: Chromophore 1 Amentioning

confidence: 99%

“…On the other hand, recent theoretical and experimental studies showed that proper involvement of thiophene, pyrrole, and furan rings in the chromophore backbone may bring organic materials with advanced properties. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] Despite their popularity as auxiliary donors, [32] a combination of five-membered heterocyclic and mesomeric donors has been practically realized only on thiophene. [33][34][35] Pyrrole or furan π-linkers with appended alkoxy or amino mesomeric donors are scarce.…”

Section: Introductionmentioning

confidence: 99%

“…Other basic five‐membered heteroaromatics such as pyrrole and furan are generally less employed in D‐π‐A molecules, mostly due to their lower polarizability and chemical instability. On the other hand, recent theoretical and experimental studies showed that proper involvement of thiophene, pyrrole, and furan rings in the chromophore backbone may bring organic materials with advanced properties [14–21,22–31] . Despite their popularity as auxiliary donors, [32] a combination of five‐membered heterocyclic and mesomeric donors has been practically realized only on thiophene [33–35] .…”

Section: Introductionmentioning

confidence: 99%

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Small Heterocyclic D‐π‐D‐π‐A Push‐Pull Molecules with Complex Electron Donors

et al. 2021

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A large series of small push-pull chromophores based on electron-withdrawing N,N'-dibutylthiobarbituric acid has been designed and successfully synthesized. The electron donating part involves common mesomeric donors such as methoxy, N,N-dimethylamino, N,N-diphenylamino, and piperidin-1-yl groups. Five-membered heteroaromatics, namely thiophene, Nmethylpyrrole, and furan have been employed as electron rich π-linkers and auxiliary donors. Structural analogues bearing aromatic 1,4-phenylene linker were also synthesized for comparison. Fundamental thermal and optoelectronic properties were studied by differential scanning calorimetry, cyclic voltammetry, and absorption spectroscopy. Thorough structureproperty relationships were elucidated, focusing mostly on type of the used π-linker and donor. All experimental conclusions are corroborated by theoretical calculations. The study has shown that a complex donor moiety may be built by properly combining mesomeric and auxiliary donors. Whereas strong mesomeric donor (amino) suppresses the donating effect of auxiliary donors/π-linkers, a combination of weak donor (methoxy) appended at a five-membered heterocycle pronounces the donating ability of the latter.

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“…Recently, Bulumulla et.al., reviewed the synthesis of pyrrole containing semiconducting materials and their applications in organic photovoltaics and organic field-effect transistors [12]. The derivatives of pyrrole have been explored as photoactive material in optical thermometry and thermography [13], fluorophores [14,15], photovoltaics [16], photochromism [17], luminescent and display materials [18], solar cells [19,20], semiconductors [21,22], fluorescent probes [23], molecules with NLO properties [24], optoelectronic applications due to structural modification of π-acceptors [25], absorption, fluorescence, phosphorescence and quantum yields [26], because of their inherent photophysical characteristics. These are also used as electric and optical sensor material for pH detection [27], optical chemosensor for Cu 2+ and sensor for pyrophosphate [28], in electropolymerization [29].…”

Section: Introductionmentioning

confidence: 99%

Photophysical Approach of Biological Active Benzofuran Derivatized Pyrrole with Green Synthesized Silver NPs Using C. Roseus Leaves: Computational and Spectroscopic Study

Patil¹,

Basanagouda²,

Hiremath³

et al. 2021

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The electronic absorption and fluorescence emission spectra of N-(2,5-dimethyl-pyrrol-1-yl)-2-(5-methoxybenzofuran-3-yl)acetamide (DPMA) molecule were recorded in various solvents at room temperature with the aim of estimation of ground state (\({\mu }_{g}\)) and excited states (\({\mu }_{e}\)) dipole moments using Lippert’s, Bakshiev’s and Kawski-Chamma-Viallete’s equations. The results were signified that, the excited state dipole moment is greater than the ground state dipole moment, which indicates the excited state dipole moment is more polar than the ground state dipole moment. Ecofriendly green synthesis of silver nanoparticles (Ag NPs) were synthesized using catharanthus roseus (C.R) leaf extract was done. These synthesized Ag NPs were used as fluorescence quenchers. Fluorescence lifetime measurement is carried out using time correlated single photon counting technique of DPMA molecule with various concentrations of Ag NPs. A linear Stern-Volmer (S-V) plot was obtained in steady state and transient state method. Furthermore we have estimated computational calculations such as ground state optimized geometry, molecular electrostatic potential (MEP), highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), experimental and theoretical energy band gap, solvent polarity and normalized solvent polarity values. Morphology and sizes of green synthesized silver NPs were characterized by transmission electron microscopy (TEM) with energy dispersive X-ray spectroscopy (EDX) and also characterized by UV-Visible absorption.

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DFT-TDDFT framework of diphenylamine based mixed valence compounds for optoelectronic applications – Structural modification of π-acceptors

Cited by 14 publications

References 64 publications

Electronic and Optical Properties of Polythiophene Molecules and Derivatives

Electronic and Optical Properties of Polythiophene Molecules and Derivatives

Small Heterocyclic D‐π‐D‐π‐A Push‐Pull Molecules with Complex Electron Donors

Photophysical Approach of Biological Active Benzofuran Derivatized Pyrrole with Green Synthesized Silver NPs Using C. Roseus Leaves: Computational and Spectroscopic Study

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