Computational investigation of charge injection and transport properties of a series of thiophene–pyrrole based oligo-azomethines

Sahu, Harikrishna; Panda, Aditya N.

doi:10.1039/c3cp55243h

Cited by 64 publications

(103 citation statements)

References 98 publications

(106 reference statements)

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“…98 In the case of hole transport, t 12 + values calculated for polymers I -V, especially for II and IV, are comparable to the values reported for oligomers such as oligothiophene with n = 6 (0.135 eV, calculated at the B3LYP/6-31G** level), short oligomers formed by thiophene rings and fluoroarenes-thiophenes (0.031 − 0.057 eV, calculated at the B3LYP/6-31G** level), 98 and compounds such as thiophene-pyrrole based oligoazomethines. 99 It is worth mentioning the strong differences calculated for the electron couplings of the polymers III and IV which present related structures. In this case, the higher number of fused rings can be associated to the increase of the coupling between neighboriong rings.…”

Section: Acs Paragon Plus Environmentmentioning

confidence: 99%

Optoelectronic and Semiconducting Properties of Conjugated Polymers Composed of Thiazolo[5,4-d]thiazole and Arene Imides Linked by Ethynylene Bridges

et al. 2016

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A set of engineered crystalline polymers containing thiazolo [5,4-d]thiazole and arene imides linked by ethynylene bridges have been modelled by means of Density Functional Theory (periodic boundary) calculations. A large set of relevant electronic properties related to the opto-electronic and semiconductor character of these systems, such as optical band gap, frontier molecular orbital energy levels, electron affinity, ionization potential, reorganization energy, and electronic coupling between neighboring polymer chains were obtained. We further discuss the effect of the ethynylene linkages, the presence of heteroatoms in thiazolo [5,4-d]thiazole rings, and

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Section: Acs Paragon Plus Environmentmentioning

confidence: 99%

Optoelectronic and Semiconducting Properties of Conjugated Polymers Composed of Thiazolo[5,4-d]thiazole and Arene Imides Linked by Ethynylene Bridges

et al. 2016

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“…Generally, at room temperature or for less ordered systems, charge transport takes place predominately by the hopping mechanism, and the charge transfer rate ( K CT ) between two adjacent organic molecules is defined by Marcus theory:

K_{CT} = ((), \frac{t^{2}}{normalℏ}) {(\frac{π}{λ k_{B} T})}^{1 / 2} \exp ((), \frac{- λ}{4 k_{B} T})

where λ is the reorganization energy, k B is the Boltzmann Constant, T is temperature ( T = 298.15 K), ℏ is reduced Planck's constant, and t is the charge transfer integral (electronic coupling) between two adjacent molecules. In this work, we have considered only the internal or inner‐sphere reorganization energy ( λ = λ int ) neglecting the effect of the polarization of the surrounding medium that is calculated as the energy difference between the neutral and charge state of the compounds …”

Section: Resultsmentioning

confidence: 99%

“…In this work, we have considered only the internal or inner-sphere reorganization energy (λ = λ int ) neglecting the effect of the polarization of the surrounding medium that is calculated as the energy difference between the neutral and charge state of the compounds. [74] Because the donor compounds are predominately characterized by the hole carriers, therefore, we have discussed their hole transport properties.…”

Section: Charge Transport Propertiesmentioning

confidence: 99%

Effect of electron‐withdrawing groups on photovoltaic performance of thiophene‐vinyl‐thiophene derivative and benzochalcogenadiazole based copolymers: A computational study

Bhattacharya

Sahoo

Sharma

et al. 2019

Int J of Quantum Chemistry

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We report a density functional theory study of the effect of electron-withdrawing groups such as -F, -CN, -NO 2 on the geometrical, optoelectronic, intramolecular charge transfer (ICT), and photovoltaic properties of (E)-1,2-bis(5-alkyl-[2,3 0bithiophene]-2 0 -yl)ethene (TVT-T) based donor-acceptor (D-A) copolymers with different acceptor units, that is, benzo[c] [1,2,5]thiadiazole, benzo[c][1,2,5]oxadiazole, and benzo[c][1,2,5]selenadiazole. The computed optical absorption spectra of the designed compounds lie in the visible and near-infrared regions. Of all the studied copolymers, -CN substituted and Se-based compound displays the lowest HOMO-LUMO (E H -L ) gap and optical band gap (E opt ). The exciton binding energy (E b ) is found to be smaller for O-incorporated compounds and -CN substituted copolymer as well, inferring more ICT.The electron-hole coherence concentrated over the D-A units is nearly the same for -CN and -NO 2 substituted compounds, but larger in -F derivatives, indicating weak electronhole coupling in the formers. Comparatively larger dipole moment (6.421 Debye-9.829 Debye) and charge transfer length (D CT ) (1.976 Å-3.122 Å) for -CN derivatives lead to enhanced ICT properties. The designed donors yield good hole mobilities (0.127-6.61 cm 2 V −1 s −1 ) and the predicted power conversion efficiencies are calculated to be as high as~6%-7% for -CN and -NO 2 substituted compounds. K E Y W O R D SDFT, donor-acceptor copolymer, electron-withdrawing groups, Intramolecular charge transfer, power conversion efficiency | INTRODUCTIONOrganic solar cells (OSC) or organic photovoltaics (OPVs) incorporating conjugated polymers (CPs) have been a thrust area of research due to their diverse potential applications. In addition, these materials are envisaged to be highly cost-effective, lightweight, mechanically flexible, environmentally benign and hence are considered as efficacious alternatives to the conventional inorganic solar cell. [1][2][3][4][5] The highest achieved power conversion efficiency (PCE) of bulk heterojunction OPV devices containing CPs as donor materials and fullerene derivatives as acceptor units were reported so far to be over 11%. [6][7][8] Conventional organic materials naturally have band gap greater than 2 eV encompassing the only visible range of the solar spectra (300-650 nm). However, to achieve high PCE, materials need to have a lower band gap as well as deeper highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels. A deep HOMO level increases the open circuit voltage

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“…[53,65,66] The geometries of all the fused thiophene semiconductors in the neutral and charged states are optimized using the B3LYP hybrid functional [67,68] and 6-31G** basis set. [51,[69][70][71][72] The frontier molecular orbitals are also obtained based on the B3LYP/6-31G** level. The vibrational frequencies are calculated at the same level on the basis of the resulting optimized geometries to confirm the accuracy of the results.…”

Section: Theoretical Methodologymentioning

confidence: 99%

“…The geometries of all the fused thiophene semiconductors in the neutral and charged states are optimized using the B3LYP hybrid functional and 6‐31G** basis set . The frontier molecular orbitals are also obtained based on the B3LYP/6‐31G** level.…”

Section: Theoretical Methodologymentioning

confidence: 99%

The impact of diperfluorophenyl and thienyl substituents on the electronic structures and charge transport properties of the fused thiophene semiconductors

Wang

Dai

Song

2018

Int J of Quantum Chemistry

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The charge transport properties of 3 fused thiophene semiconductors, end‐capped with diperfluorophenylthien‐2‐yl (DFPT) groups (DFPT‐thieno[2′, 3′:4, 5]thieno[3, 2‐b]thieno[2, 3‐d]thiophene (TTA), DFPT‐dithieno[2, 3‐b:3′, 2′‐d]thiophenes (DTT), and DFPT‐thieno[3, 2‐b]thiophene (TT)), are explored via density functional theory (DFT). To gain a better understanding of the impact of diperfluorophenyl and thienyl substituents on the electronic structures and charge transport properties of these molecules, the geometric structures, reorganization energy, frontier molecular orbitals, molecular ionization potentials and electron affinities, absorption spectra of the corresponding molecules including diperfluorophenyl (DFP)‐TTA, DFP‐DTT, DFP‐TT, dithienyl (DT)‐TTA, DT‐DTT, DT‐TT as well as their parent molecules (TTA, DTT and TT) are investigated for comparison. The calculated results show that introducing perfluorophenyl groups to the fused thiophenes could be a good strategy to promote electron transport, while the insertion of additional thiophene rings to DFP‐end‐capped derivatives could further extend the π‐conjugation and enhance the charge transport properties of DFPT‐end‐capped analogs.

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Computational investigation of charge injection and transport properties of a series of thiophene–pyrrole based oligo-azomethines

Cited by 64 publications

References 98 publications

Optoelectronic and Semiconducting Properties of Conjugated Polymers Composed of Thiazolo[5,4-d]thiazole and Arene Imides Linked by Ethynylene Bridges

Optoelectronic and Semiconducting Properties of Conjugated Polymers Composed of Thiazolo[5,4-d]thiazole and Arene Imides Linked by Ethynylene Bridges

Effect of electron‐withdrawing groups on photovoltaic performance of thiophene‐vinyl‐thiophene derivative and benzochalcogenadiazole based copolymers: A computational study

The impact of diperfluorophenyl and thienyl substituents on the electronic structures and charge transport properties of the fused thiophene semiconductors

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