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

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

doi:10.1021/acsenergylett.2c00684

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

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

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

38 Scopus citations

Abstract

High-performance and durable perovskite solar cells (PSCs) have advanced rapidly, enabled in part by the development of superior interfacial hole-transporting layers (HTLs). Here, a new series of 2,3-diphenylthieno[3,4-b]pyrazine (DPTP)-based small molecules containing bis- and tetrakis-triphenyl amino donors (1-3) was synthesized from simple, low-cost, and readily available starting materials. The matched energy levels, ideal surface topographies, high hole mobilities of 8.57 × 10^-4cm²V^-1S^-1, and stable chemical structures of DPTP-4D (3) make it an effective hole-transporting material, delivering a PCE of 20.18% with high environmental, thermal, and light-soaking stability when compared to the reference HTL materials, doped Spiro-OMeTAD and PTAA in PSC n-i-p planar devices. Overall, these DPTP-based molecules are promising HTM candidates for the fabrication of stable PSCs.

Original language	English (US)
Pages (from-to)	2118-2127
Number of pages	10
Journal	ACS Energy Letters
Volume	7
Issue number	6
DOIs	https://doi.org/10.1021/acsenergylett.2c00684
State	Published - Jun 10 2022

Funding

M.-C.C. thanks the Ministry of Science and Technology of Taiwan (MOST 109-2113-M-008-011-MY2) and National Central University-Covestro Research Center (MOST 110-2622-8-008-007) for the financial support provided. T.J.M. thanks the US Office of Naval Research (Contract N00014-20-1-2116), and M.G.K. thanks the US Office of Naval Research (Contract N00014-20-1- 2725) for support of this work. They also thank the Northwestern University MRSEC under NSF Grant DMR-1720139 for use of the EPIC facility, Keck-II facility, and SPID facility of the NUANCE Center at Northwestern University (UPS, SEM, and AFM), which also received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205); the MRSEC program (NSF DMR-1720139); the International Institute for Nanotechnology (IIN); the Keck Foundation; and the State of Illinois. R.D.S. thanks the Center for Nanoscale Materials, a U.S. Department of Energy Office of Science User Facility, and was supported by the U.S. DOE, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357 (PL and TRPL). D.Z. and J.Y. thank the National Key R&D Program of China (Grant No. 2018YFB0407102), the National Natural Science Foundation of China (NSFC) (Grant Nos. 61421002, 61675041, and 51703019), and the Sichuan Science and Technology Program (Grant Nos. 2019YFH0005, 2019YFG0121, and 2019YJ0178) for support (synthesis and characterization).

ASJC Scopus subject areas

Chemistry (miscellaneous)
Renewable Energy, Sustainability and the Environment
Fuel Technology
Energy Engineering and Power Technology
Materials Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acsenergylett.2c00684

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Afraj, S. N., Zheng, D., Velusamy, A., Ke, W., Cuthriell, S., Zhang, X., Chen, Y., Lin, C., Ni, J. S., Wasielewski, M. R., Huang, W., Yu, J., Pan, C. H., Schaller, R. D., Chen, M. C., Kanatzidis, M. G., Facchetti, A., & Marks, T. J. (2022). 2,3-Diphenylthieno[3,4- b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells. ACS Energy Letters, 7(6), 2118-2127. https://doi.org/10.1021/acsenergylett.2c00684

@article{c5e0c72bf5f64739a06e2eda8f69cec8,

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

abstract = "High-performance and durable perovskite solar cells (PSCs) have advanced rapidly, enabled in part by the development of superior interfacial hole-transporting layers (HTLs). Here, a new series of 2,3-diphenylthieno[3,4-b]pyrazine (DPTP)-based small molecules containing bis- and tetrakis-triphenyl amino donors (1-3) was synthesized from simple, low-cost, and readily available starting materials. The matched energy levels, ideal surface topographies, high hole mobilities of 8.57 × 10-4cm2V-1S-1, and stable chemical structures of DPTP-4D (3) make it an effective hole-transporting material, delivering a PCE of 20.18% with high environmental, thermal, and light-soaking stability when compared to the reference HTL materials, doped Spiro-OMeTAD and PTAA in PSC n-i-p planar devices. Overall, these DPTP-based molecules are promising HTM candidates for the fabrication of stable PSCs.",

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

note = "Funding Information: M.-C.C. thanks the Ministry of Science and Technology of Taiwan (MOST 109-2113-M-008-011-MY2) and National Central University-Covestro Research Center (MOST 110-2622-8-008-007) for the financial support provided. T.J.M. thanks the US Office of Naval Research (Contract N00014-20-1-2116), and M.G.K. thanks the US Office of Naval Research (Contract N00014-20-1- 2725) for support of this work. They also thank the Northwestern University MRSEC under NSF Grant DMR-1720139 for use of the EPIC facility, Keck-II facility, and SPID facility of the NUANCE Center at Northwestern University (UPS, SEM, and AFM), which also received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205); the MRSEC program (NSF DMR-1720139); the International Institute for Nanotechnology (IIN); the Keck Foundation; and the State of Illinois. R.D.S. thanks the Center for Nanoscale Materials, a U.S. Department of Energy Office of Science User Facility, and was supported by the U.S. DOE, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357 (PL and TRPL). D.Z. and J.Y. thank the National Key R&D Program of China (Grant No. 2018YFB0407102), the National Natural Science Foundation of China (NSFC) (Grant Nos. 61421002, 61675041, and 51703019), and the Sichuan Science and Technology Program (Grant Nos. 2019YFH0005, 2019YFG0121, and 2019YJ0178) for support (synthesis and characterization). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

month = jun,

day = "10",

doi = "10.1021/acsenergylett.2c00684",

language = "English (US)",

volume = "7",

pages = "2118--2127",

journal = "ACS Energy Letters",

issn = "2380-8195",

publisher = "American Chemical Society",

number = "6",

}

Afraj, SN, Zheng, D, Velusamy, A, Ke, W, Cuthriell, S, Zhang, X, Chen, Y, Lin, C, Ni, JS, Wasielewski, MR, Huang, W, Yu, J, Pan, CH, Schaller, RD, Chen, MC, Kanatzidis, MG, Facchetti, A & Marks, TJ 2022, '2,3-Diphenylthieno[3,4- b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells', ACS Energy Letters, vol. 7, no. 6, pp. 2118-2127. https://doi.org/10.1021/acsenergylett.2c00684

TY - JOUR

T1 - 2,3-Diphenylthieno[3,4- b]pyrazines as Hole-Transporting Materials for Stable, High-Performance Perovskite Solar Cells

AU - Afraj, Shakil N.

AU - Zheng, Ding

AU - Velusamy, Arulmozhi

AU - Ke, Weijun

AU - Cuthriell, Shelby

AU - Zhang, Xiaohua

AU - Chen, Yao

AU - Lin, Chenjian

AU - Ni, Jen Shyang

AU - Wasielewski, Michael R.

AU - Huang, Wei

AU - Yu, Junsheng

AU - Pan, Chun Huang

AU - Schaller, Richard D.

AU - Chen, Ming Chou

AU - Kanatzidis, Mercouri G.

AU - Facchetti, Antonio

AU - Marks, Tobin J.

N1 - Funding Information: M.-C.C. thanks the Ministry of Science and Technology of Taiwan (MOST 109-2113-M-008-011-MY2) and National Central University-Covestro Research Center (MOST 110-2622-8-008-007) for the financial support provided. T.J.M. thanks the US Office of Naval Research (Contract N00014-20-1-2116), and M.G.K. thanks the US Office of Naval Research (Contract N00014-20-1- 2725) for support of this work. They also thank the Northwestern University MRSEC under NSF Grant DMR-1720139 for use of the EPIC facility, Keck-II facility, and SPID facility of the NUANCE Center at Northwestern University (UPS, SEM, and AFM), which also received support from the Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF ECCS-1542205); the MRSEC program (NSF DMR-1720139); the International Institute for Nanotechnology (IIN); the Keck Foundation; and the State of Illinois. R.D.S. thanks the Center for Nanoscale Materials, a U.S. Department of Energy Office of Science User Facility, and was supported by the U.S. DOE, Office of Basic Energy Sciences, under Contract No. DE-AC02-06CH11357 (PL and TRPL). D.Z. and J.Y. thank the National Key R&D Program of China (Grant No. 2018YFB0407102), the National Natural Science Foundation of China (NSFC) (Grant Nos. 61421002, 61675041, and 51703019), and the Sichuan Science and Technology Program (Grant Nos. 2019YFH0005, 2019YFG0121, and 2019YJ0178) for support (synthesis and characterization). Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/6/10

Y1 - 2022/6/10

N2 - High-performance and durable perovskite solar cells (PSCs) have advanced rapidly, enabled in part by the development of superior interfacial hole-transporting layers (HTLs). Here, a new series of 2,3-diphenylthieno[3,4-b]pyrazine (DPTP)-based small molecules containing bis- and tetrakis-triphenyl amino donors (1-3) was synthesized from simple, low-cost, and readily available starting materials. The matched energy levels, ideal surface topographies, high hole mobilities of 8.57 × 10-4cm2V-1S-1, and stable chemical structures of DPTP-4D (3) make it an effective hole-transporting material, delivering a PCE of 20.18% with high environmental, thermal, and light-soaking stability when compared to the reference HTL materials, doped Spiro-OMeTAD and PTAA in PSC n-i-p planar devices. Overall, these DPTP-based molecules are promising HTM candidates for the fabrication of stable PSCs.

AB - High-performance and durable perovskite solar cells (PSCs) have advanced rapidly, enabled in part by the development of superior interfacial hole-transporting layers (HTLs). Here, a new series of 2,3-diphenylthieno[3,4-b]pyrazine (DPTP)-based small molecules containing bis- and tetrakis-triphenyl amino donors (1-3) was synthesized from simple, low-cost, and readily available starting materials. The matched energy levels, ideal surface topographies, high hole mobilities of 8.57 × 10-4cm2V-1S-1, and stable chemical structures of DPTP-4D (3) make it an effective hole-transporting material, delivering a PCE of 20.18% with high environmental, thermal, and light-soaking stability when compared to the reference HTL materials, doped Spiro-OMeTAD and PTAA in PSC n-i-p planar devices. Overall, these DPTP-based molecules are promising HTM candidates for the fabrication of stable PSCs.

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UR - http://www.scopus.com/inward/citedby.url?scp=85132025859&partnerID=8YFLogxK

U2 - 10.1021/acsenergylett.2c00684

DO - 10.1021/acsenergylett.2c00684

M3 - Article

AN - SCOPUS:85132025859

SN - 2380-8195

VL - 7

SP - 2118

EP - 2127

JO - ACS Energy Letters

JF - ACS Energy Letters

IS - 6

ER -

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

Abstract

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UN SDGs

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