Theoretical study of the fluorination effect on charge transport properties in fused thiophene derivatives

Yin, Jun; Chaitanya, Kadali; Ju, Xue‐Hai

doi:10.1039/c5ra06418j

Cited by 11 publications

(10 citation statements)

References 62 publications

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“…The Polymorph module in Materials Studio 8.0 software package was used to predict the crystal structures of the studied compounds . Based on the obtained crystal structures, the charge-transfer integral calculation was performed at PW91PW91/6-31G (d, p) level, which gave the results very close to the experimental ones …”

Section: Computational Detailsmentioning

confidence: 65%

“…45 Based on the obtained crystal structures, the charge-transfer integral calculation was performed at PW91PW91/6-31G (d, p) level, which gave the results very close to the experimental ones. 67 In the calculations on the MAPbI 3 /ETM interface, we chose the widely used PbI 2 -terminated 110-MAPbI 3 surface in the tetragonal phase. Our slab models have a 4 × 4 periodicity inplane, and a 20 Å vacuum region was added.…”

Section: Computational Detailsmentioning

confidence: 99%

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Molecular Engineering of Hexaazatriphenylene Derivatives toward More Efficient Electron-Transporting Materials for Inverted Perovskite Solar Cells

Zhu

2020

ACS Appl. Mater. Interfaces

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The electron-transporting material (ETM) in inverted perovskite solar cells (PSCs) plays important role in reducing hysteresis and realizing simple processing procedures, while the improvement of power conversion efficiency is limited by low electron mobility and weak perovskite/ETM interface interaction. In this work, three new ETMs (HAT-1, HAT-2, and HAT-3) were designed by introducing methoxyphenyl, imide, and naphthalene groups into the hexaazatriphenylene (HAT) skeleton, based on the ETM HATNASOC7 synthesized experimentally [Jen; et al. Angew. Chem., Int. Ed. 2016, 55, 8999]. Theoretical calculations showed that the electron mobilities of HAT-1, HAT-2, and HAT-3 are 2.98, 3.79, and 13.21 times that of HATNASOC7, which is attributed to the increased C•••C and O•••H interactions in the newly designed ETMs. More importantly, the evidently decreased perovskite/ETM interface distances and the significantly increased adsorption energies revealed that the interface interactions were markedly enhanced with the newly designed ETMs by forming additional Pb••• O interactions, which promote the electron injection. The deep understanding of perovskite/ ETM interface properties sheds new light on the complex factors determining the PSC function and paves the way for the rational design of highly efficient and stable components for PSCs.

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Section: Computational Detailsmentioning

confidence: 65%

Section: Computational Detailsmentioning

confidence: 99%

Molecular Engineering of Hexaazatriphenylene Derivatives toward More Efficient Electron-Transporting Materials for Inverted Perovskite Solar Cells

Zhu

2020

ACS Appl. Mater. Interfaces

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“…Comparing with DT‐DTT and DFP‐DTT, when only introducing the thiophene unit and perfluorophenyl substituents to the parent molecule DTT, DT‐DTT and DFP‐DTT change into a herringbone stacking motif, respectively. The calculated transfer integrals show that T‐DTT (see Supporting Information Table S6) and DFP‐DTT facilitate to hole transport similar to DFPT‐DTT. However, when increasing the central thiophene core to 4 rings, the crystal packing motif of DFPT‐TTA is changed to herringbone packing motif, and main pathways 1 and 2 exhibit larger transfer integrals for both hole (109.1 meV) and electron (47.2 meV), in which the transfer integrals of hole is much larger than that of electron, indicating that it is beneficial to hole transport.…”

Section: Resultsmentioning

confidence: 99%

“…Theoretical simulations provide an effective way to understand the structure‐property relationships in OSCs and will aid in the design of high‐performance materials experimentally. Based on the first principle calculations, Yin et al explored the fluorination effect on the charge transport properties in fused thiophene derivatives, demonstrating that fluorination of these molecules could be an effective way to improve their charge mobilities. Wei and co‐workers investigated a series of phenyl end‐capped derivatives of benzo[ d , d ’]thieno[3,2‐b;4,5‐ b ′]dithiophene (BTDT) with periphery‐fluorinated substitutions (PFS).…”

Section: Introductionmentioning

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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“…The optimized bond lengths of HTP is in good agreement with the single crystal X-ray diffraction structure (Table I) The electronic structures and energies of frontier molecular orbitals influence the charge transfer greatly. 24 As seen from the contours of Fig. 2, the HOMO is symmetric, while LUMO is asymmetric.…”

Section: Geometrical Structuresmentioning

confidence: 87%

Study on charge mobility of hexathiapentacene and its selenium analogs

Zhou

Xia

Meng

et al. 2021

JSCS

Self Cite

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The relationship between molecular geometries, crystal structures and charge mobilities of hexathiapentacene (HTP) and its three derivatives (2Se-HTP, 4Se-HTP, 6Se-HTP) were studied with density functional theory combined with hopping mechanism in the molecular and crystal level. The effect of Se substitution on the charge mobility was discussed. The calculated results showed that the derivatives exhibit good planarity and the molecular geometries have little variation during the charge transfer process. The electron mobility is 1.20 cm2 V?1 S?1 for HTP and 2.30 cm2 V?1 S?1 for 6Se-HTP, which are much larger than the corresponding hole ones, indicating that HTP and 6Se-HTP are good candidates for n-type organic semiconductor. However, 2Se-HTP and 4Se-HTP have comparable hole and electron mobilities and are suitable for ambipolar semiconductor.

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Theoretical study of the fluorination effect on charge transport properties in fused thiophene derivatives

Abstract: To gain a better understanding of the fluorination effect on the charge transport property,

Cited by 11 publications

References 62 publications

Molecular Engineering of Hexaazatriphenylene Derivatives toward More Efficient Electron-Transporting Materials for Inverted Perovskite Solar Cells

Molecular Engineering of Hexaazatriphenylene Derivatives toward More Efficient Electron-Transporting Materials for Inverted Perovskite Solar Cells

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

Study on charge mobility of hexathiapentacene and its selenium analogs

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