2,3-Diphenylthieno[3,4-<i>b</i>]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells

Afraj, Shakil N.; Zheng, Ding; Velusamy, Arulmozhi; Ke, Weijun; Cuthriell, Shelby A.; Zhang, Xiaohua; Chen, Yao; Lin, Chenjian; Ni, Jen‐Shyang; Wasielewski, Michael R.; Huang, Wei; Yu, Junsheng; Pan, Chun-Huang; Schaller, Richard D.; Chen, Ming-Chou; Kanatzidis, Mercouri G.; Facchetti, Antonio; Marks, Tobin J.

doi:10.1021/acsenergylett.2c00684

Cited by 37 publications

(32 citation statements)

References 64 publications

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“…Recently, we have designed and developed efficient HTMs, DImBT‐4D ( 108) and DPTP‐4D ( 109), which deliver PCEs of 20.11% and 20.18%, respectively, in Pb‐based PSC. [ 68 ] Both new HTLs exhibit higher environmental, thermal, and light‐soaking stability. In addition, these newly established fused thiophene cores could also be used in NFAs development, for example, dicyclopentadithienothiophene (DCDTT)‐core which has been applied in Pb‐based PSC and achieved PCE of 21.39 and 17.18% by spin‐coating and spray‐coating process, respectively, for the compound 110 .…”

Section: New Hole‐transporting Materials (Htm) and Non‐fullerene Acce...mentioning

confidence: 99%

Fused thiophene based materials for organic thin‐film transistors

Velusamy

Afraj

Yau

et al. 2022

J Chinese Chemical Soc

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Section: New Hole‐transporting Materials (Htm) and Non‐fullerene Acce...mentioning

confidence: 99%

Fused thiophene based materials for organic thin‐film transistors

Velusamy

Afraj

Yau

et al. 2022

J Chinese Chemical Soc

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“…In the modern study of organic optoelectronics, integrating an electron donor (D) and an electron acceptor (A) in a molecule enables adjustable HOMO/LUMO energy levels and faster hole/electron transporting mobility. , This view is illustrated by having a thienopyrazine-based terthienyl (TP-based TT) analogue, such as 2,3-diphenyl-5,7-di(thiophen-2-yl)thieno[3,4- b ]pyrazine (DPDTTP, shown in Scheme ), as a building block for a series of organic polymers and photovoltaic materials with low band gaps. , TP-based TT is a strong electron-withdrawing group, which can enhance the intramolecular charge transfer within the D–A–D organic molecules, leading to a higher charge mobility. , Moreover, when two bulky phenyl groups are attached to the acceptor backbone (TP unit), aggregation of the hole transporting molecules is suppressed, yielding an ideal morphology for the subsequently prepared thin and better performing perovskite solar cells. − The charge injection at a typical organic/metal interface can vary with the orientation of the molecule.…”

Section: Introductionmentioning

confidence: 99%

Potential-Controlled Organization of 2,3-Diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine Adsorbed on Au(111) and Au(100) Electrodes

et al. 2022

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The 2,3-diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine (DPDTTP) molecule is an organic molecule that is often used to produce photovoltaics and light-emitting diodes. The orientation of an organic semiconductor molecule at the metallic interface can affect the charge injection efficiency. The current study employed in situ scanning tunneling microscopy (STM) to examine the adsorption orientation of DPDTTP molecules on an ordered Au(111) electrode in 0.1 M HClO4, H2SO4, and HCl. DPDTTP molecules were found to irreversibly adsorbed onto the Au electrode from a 10 μM dosing solution. Molecular-resolution STM images were obtained to reveal their spatial structure as functions of the chemical identity of the supporting electrolyte, the atomic structure of the Au(111) substrate, and the potential control. Only the reconstructed Au(111) electrode afforded ordered DPDTTP adlattices between −0.1 and 0.4 V (vs Ag/AgCl) in HClO4 and H2SO4, and the DPDTTP adlayer became more compact with more positive potential. In 0.1 M HCl, pre-adsorbed DPDTTP molecules on the Au(111) electrode were displaced by chloride anions at E > 0.2 V, as evidenced by a well-ordered hexagonal array with a nearest-neighbor spacing of 3.8 ± 0.1 Å. The DPDTTP admolecule desorbed at E < −0.1 V in all acids. High-quality STM images were acquired to reveal two kinds of molecular conformations, as also found in the bulk single crystal of DPDTTP. The prominent role of the reconstructed structure in guiding the formation of ordered DPDTTP structures was substantiated by examining DPDTTP adsorbed on the Au(100) electrode in HClO4.

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“…[ 124,107 ] Newly‐developed functional materials that integrate not only charge extraction ability but also encapsulating property, as well as defect passivation, are highly desired to simultaneously improve photovoltaic performance and device stability. [ 125,126 ]…”

Section: Discussionmentioning

confidence: 99%

Spiro‐OMeTAD‐Based Hole Transport Layer Engineering toward Stable Perovskite Solar Cells

Shen

Deng

2022

Small Methods

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Perovskite solar cells (PSCs) have undergone unprecedented growth in the past decade as an emerging photovoltaic technology. Up till now, the power conversion efficiency of PSCs has exceeded 25% that rivals silicon solar cells and there is still room for further enhancement. However, the development in long‐term stability lags far behind, which remains a great concern for the commercial application in the future. The device instability mainly arises from the functional components, including perovskite film, charge transport layers, and electrodes along with the involved interfaces. As the most widely studied hole transport layer at the current stage, 2,2′,7,7′‐tetrakis(N,N‐di(4‐methoxyphenyl)amino)‐9,9‐spirobifluorene (Spiro‐OMeTAD) helps contribute to the achievement of record efficiency but it weakens the device stability due to the doping‐induced side effects such as hygroscopicity and ion migration. Great efforts are devoted to boosting the stability of Spiro‐OMeTAD while maintaining excellent photovoltaic performance. In this review, the fundamental properties of Spiro‐OMeTAD have been summarized and the recent advances in engineering Spiro‐OMeTAD‐based hole transport layer for the sake of highly efficient PSCs with enhanced longevity are highlighted. In the end, an outlook for the further optimization of Spiro‐OMeTAD is provided and the issues related to large‐scale production are discussed.

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2,3-Diphenylthieno[3,4-b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells

Cited by 37 publications

References 64 publications

Fused thiophene based materials for organic thin‐film transistors

Fused thiophene based materials for organic thin‐film transistors

Potential-Controlled Organization of 2,3-Diphenyl-5,7-di(thiophen-2-yl)thieno[3,4-b]pyrazine Adsorbed on Au(111) and Au(100) Electrodes

Spiro‐OMeTAD‐Based Hole Transport Layer Engineering toward Stable Perovskite Solar Cells

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