Facile synthesis of high-performance nonfullerene acceptor isomers via a one stone two birds strategy

Tengfei Li; Langxuan Yang; Yiqun Xiao; Kuan Liu; Jiayu Wang; Xinhui Lu; Xiaowei Zhan

doi:10.1039/c9ta07917c

Facile synthesis of high-performance nonfullerene acceptor isomers via a one stone two birds strategy

Tengfei Li, Langxuan Yang, Yiqun Xiao, Kuan Liu, Jiayu Wang, Xinhui Lu, Xiaowei Zhan

Research output: Journal article publication › Journal article › Academic research › peer-review

19 Citations (Scopus)

Abstract

Two isomeric fused undecacyclic electron acceptors (FUIC and i-FUIC) are designed and synthesized via a one stone two birds strategy based on core unit 4TT (four thienothiophene units condensed with three cyclopentadienyl rings) and end groups 2FIC (2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)-malononitrile). The only difference is the two attachment positions between 4TT and 2FIC, α, α-positions for FUIC and α, β-positions for i-FUIC. FUIC exhibits stronger and red-shifted absorption with an ultra-narrow bandgap of 1.22 eV (1.28 eV for i-FUIC), a down-shifted lowest unoccupied molecular orbital energy level of -4.06 eV (-3.99 eV for i-FUIC), the same highest occupied molecular orbital energy level of -5.31 eV and a higher electron mobility of 6.8 × 10^-4 cm² V^-1 s^-1 (3.0 × 10^-4 cm² V^-1 s^-1 for i-FUIC). Organic solar cells based on a blend of PTB7-Th:FUIC exhibit a power conversion efficiency as high as 11.2% with a high fill factor of 70.6%, higher than that of PTB7-Th:i-FUIC (10.3%).

Original language	English
Pages (from-to)	20667-20674
Number of pages	8
Journal	Journal of Materials Chemistry A
Volume	7
Issue number	36
DOIs	https://doi.org/10.1039/c9ta07917c
Publication status	Published - Aug 2019

ASJC Scopus subject areas

Chemistry(all)
Renewable Energy, Sustainability and the Environment
Materials Science(all)

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

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10.1039/c9ta07917c

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title = "Facile synthesis of high-performance nonfullerene acceptor isomers via a one stone two birds strategy",

abstract = "Two isomeric fused undecacyclic electron acceptors (FUIC and i-FUIC) are designed and synthesized via a one stone two birds strategy based on core unit 4TT (four thienothiophene units condensed with three cyclopentadienyl rings) and end groups 2FIC (2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)-malononitrile). The only difference is the two attachment positions between 4TT and 2FIC, α, α-positions for FUIC and α, β-positions for i-FUIC. FUIC exhibits stronger and red-shifted absorption with an ultra-narrow bandgap of 1.22 eV (1.28 eV for i-FUIC), a down-shifted lowest unoccupied molecular orbital energy level of -4.06 eV (-3.99 eV for i-FUIC), the same highest occupied molecular orbital energy level of -5.31 eV and a higher electron mobility of 6.8 × 10-4 cm2 V-1 s-1 (3.0 × 10-4 cm2 V-1 s-1 for i-FUIC). Organic solar cells based on a blend of PTB7-Th:FUIC exhibit a power conversion efficiency as high as 11.2% with a high fill factor of 70.6%, higher than that of PTB7-Th:i-FUIC (10.3%).",

author = "Tengfei Li and Langxuan Yang and Yiqun Xiao and Kuan Liu and Jiayu Wang and Xinhui Lu and Xiaowei Zhan",

note = "Funding Information: X. Z. thanks the NSFC (No. 51761165023 and 21734001). X. L. is thankful for the nancial support from NSFC/RGC Joint Research Scheme No. N_CUHK418/17 and CUHK Direct Grant. The Supercomputing Center of the Chinese Academy of Sciences is acknowledged for molecular modelling. Publisher Copyright: {\textcopyright} 2019 The Royal Society of Chemistry.",

year = "2019",

month = aug,

doi = "10.1039/c9ta07917c",

language = "English",

volume = "7",

pages = "20667--20674",

journal = "Journal of Materials Chemistry A",

issn = "2050-7488",

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TY - JOUR

T1 - Facile synthesis of high-performance nonfullerene acceptor isomers via a one stone two birds strategy

AU - Li, Tengfei

AU - Yang, Langxuan

AU - Xiao, Yiqun

AU - Liu, Kuan

AU - Wang, Jiayu

AU - Lu, Xinhui

AU - Zhan, Xiaowei

N1 - Funding Information: X. Z. thanks the NSFC (No. 51761165023 and 21734001). X. L. is thankful for the nancial support from NSFC/RGC Joint Research Scheme No. N_CUHK418/17 and CUHK Direct Grant. The Supercomputing Center of the Chinese Academy of Sciences is acknowledged for molecular modelling. Publisher Copyright: © 2019 The Royal Society of Chemistry.

PY - 2019/8

Y1 - 2019/8

N2 - Two isomeric fused undecacyclic electron acceptors (FUIC and i-FUIC) are designed and synthesized via a one stone two birds strategy based on core unit 4TT (four thienothiophene units condensed with three cyclopentadienyl rings) and end groups 2FIC (2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)-malononitrile). The only difference is the two attachment positions between 4TT and 2FIC, α, α-positions for FUIC and α, β-positions for i-FUIC. FUIC exhibits stronger and red-shifted absorption with an ultra-narrow bandgap of 1.22 eV (1.28 eV for i-FUIC), a down-shifted lowest unoccupied molecular orbital energy level of -4.06 eV (-3.99 eV for i-FUIC), the same highest occupied molecular orbital energy level of -5.31 eV and a higher electron mobility of 6.8 × 10-4 cm2 V-1 s-1 (3.0 × 10-4 cm2 V-1 s-1 for i-FUIC). Organic solar cells based on a blend of PTB7-Th:FUIC exhibit a power conversion efficiency as high as 11.2% with a high fill factor of 70.6%, higher than that of PTB7-Th:i-FUIC (10.3%).

AB - Two isomeric fused undecacyclic electron acceptors (FUIC and i-FUIC) are designed and synthesized via a one stone two birds strategy based on core unit 4TT (four thienothiophene units condensed with three cyclopentadienyl rings) and end groups 2FIC (2-(5,6-difluoro-3-oxo-2,3-dihydro-1H-inden-1-ylidene)-malononitrile). The only difference is the two attachment positions between 4TT and 2FIC, α, α-positions for FUIC and α, β-positions for i-FUIC. FUIC exhibits stronger and red-shifted absorption with an ultra-narrow bandgap of 1.22 eV (1.28 eV for i-FUIC), a down-shifted lowest unoccupied molecular orbital energy level of -4.06 eV (-3.99 eV for i-FUIC), the same highest occupied molecular orbital energy level of -5.31 eV and a higher electron mobility of 6.8 × 10-4 cm2 V-1 s-1 (3.0 × 10-4 cm2 V-1 s-1 for i-FUIC). Organic solar cells based on a blend of PTB7-Th:FUIC exhibit a power conversion efficiency as high as 11.2% with a high fill factor of 70.6%, higher than that of PTB7-Th:i-FUIC (10.3%).

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U2 - 10.1039/c9ta07917c

DO - 10.1039/c9ta07917c

M3 - Journal article

AN - SCOPUS:85072339716

SN - 2050-7488

VL - 7

SP - 20667

EP - 20674

JO - Journal of Materials Chemistry A

JF - Journal of Materials Chemistry A

IS - 36

ER -

Facile synthesis of high-performance nonfullerene acceptor isomers via a one stone two birds strategy

Abstract

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