An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors
Abstract
A new electron-deficient unit with fused 5-heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with cyclohepta- 4,6-diene-1,3-diimde unit. The imide bridging endows BBI with fixed planar configuration and both low the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbit (LUMO) energy levels. Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm2 V-1 s-1, which indicates that the BBI is a promising ntype semiconductor for optoelectronics.
- Authors:
-
[1];
- Soochow Univ., Suzhou (China). Inst. of Functional Nano & Soft Materials (FUNSOM)
- Peking Univ., Beijing (China). Beijing National Lab. for Molecular Sciences, Key Lab. of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Key Lab. of Polymer Chemistry and Physics of Ministry of Education, Center for Soft Matter Science and Engineering, College of Chemistry and Molecular Engineering
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS)
- Argonne National Lab. (ANL), Lemont, IL (United States). Science Div.
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States); Argonne National Laboratory (ANL), Argonne, IL (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division; National Natural Science Foundation of China (NSFC)
- OSTI Identifier:
- 1427654
- Alternate Identifier(s):
- OSTI ID: 1398725; OSTI ID: 1411169
- Grant/Contract Number:
- AC05-00OR22725; AC02-06CH11357; 21504062; 21572152
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Volume: 23; Journal Issue: 59; Journal ID: ISSN 0947-6539
- Publisher:
- ChemPubSoc Europe
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 77 NANOSCIENCE AND NANOTECHNOLOGY; 36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; electron-deficiency; fused rings; imides; organic semiconductors; thiophenes; electron-deficient; imide; ladder-type
Citation Formats
Wu, Fu-Peng, Un, Hio-Ieng, Li, Yongxi, Hu, Hailiang, Yuan, Yi, Yang, Bin, Xiao, Kai, Chen, Wei, Wang, Jie-Yu, Jiang, Zuo-Quan, Pei, Jian, and Liao, Liang-Sheng. An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors. United States: N. p., 2017.
Web. doi:10.1002/chem.201703415.
Wu, Fu-Peng, Un, Hio-Ieng, Li, Yongxi, Hu, Hailiang, Yuan, Yi, Yang, Bin, Xiao, Kai, Chen, Wei, Wang, Jie-Yu, Jiang, Zuo-Quan, Pei, Jian, & Liao, Liang-Sheng. An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors. United States. https://doi.org/10.1002/chem.201703415
Wu, Fu-Peng, Un, Hio-Ieng, Li, Yongxi, Hu, Hailiang, Yuan, Yi, Yang, Bin, Xiao, Kai, Chen, Wei, Wang, Jie-Yu, Jiang, Zuo-Quan, Pei, Jian, and Liao, Liang-Sheng. Mon .
"An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors". United States. https://doi.org/10.1002/chem.201703415. https://www.osti.gov/servlets/purl/1427654.
@article{osti_1427654,
title = {An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors},
author = {Wu, Fu-Peng and Un, Hio-Ieng and Li, Yongxi and Hu, Hailiang and Yuan, Yi and Yang, Bin and Xiao, Kai and Chen, Wei and Wang, Jie-Yu and Jiang, Zuo-Quan and Pei, Jian and Liao, Liang-Sheng},
abstractNote = {A new electron-deficient unit with fused 5-heterocyclic ring was developed by replacing a cyclopenta-1,3-diene from electron-rich donor indacenodithiophene (IDT) with cyclohepta- 4,6-diene-1,3-diimde unit. The imide bridging endows BBI with fixed planar configuration and both low the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbit (LUMO) energy levels. Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm2 V-1 s-1, which indicates that the BBI is a promising ntype semiconductor for optoelectronics.},
doi = {10.1002/chem.201703415},
journal = {Chemistry - A European Journal},
number = 59,
volume = 23,
place = {United States},
year = {Mon Oct 09 00:00:00 EDT 2017},
month = {Mon Oct 09 00:00:00 EDT 2017}
}
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Cited by: 12 works
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Figures / Tables:
Figure 1: (a) Imide-functionalized electron-deficient building blocks for constructing organic semiconductors. (b) Molecular design of the BBI. BBI is derivate from IDT by replacing cyclopenta-1,3-diene (blue) with cyclohepta- 4,6-diene-1,3-diimde (red). (c) The energy level diagrams of BBI and IDT by DFT calculation.
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Works referenced in this record:
Bithiophenesulfonamide Building Block for π-Conjugated Donor–Acceptor Semiconductors
journal, May 2016
- Melkonyan, Ferdinand S.; Zhao, Wei; Drees, Martin
- Journal of the American Chemical Society, Vol. 138, Issue 22
Pursuing High-Mobility n-Type Organic Semiconductors by Combination of “Molecule-Framework” and “Side-Chain” Engineering
journal, July 2016
- Zhang, Cheng; Zang, Yaping; Zhang, Fengjiao
- Advanced Materials, Vol. 28, Issue 38
Carbon-Bridged Oligo(phenylenevinylene)s: Stable π-Systems with High Responsiveness to Doping and Excitation
journal, November 2012
- Zhu, Xiaozhang; Tsuji, Hayato; López Navarrete, Juan T.
- Journal of the American Chemical Society, Vol. 134, Issue 46
Strategien für die Synthese funktioneller Naphthalindiimide
journal, June 2014
- Suraru, Sabin-Lucian; Würthner, Frank
- Angewandte Chemie, Vol. 126, Issue 29
A high-mobility electron-transporting polymer for printed transistors
journal, January 2009
- Yan, He; Chen, Zhihua; Zheng, Yan
- Nature, Vol. 457, Issue 7230, p. 679-686
Electron-Deficient Poly( p -phenylene vinylene) Provides Electron Mobility over 1 cm 2 V –1 s –1 under Ambient Conditions
journal, May 2013
- Lei, Ting; Dou, Jin-Hu; Cao, Xiao-Yu
- Journal of the American Chemical Society, Vol. 135, Issue 33
Synthesis of Ladder-Type Thienoacenes and Their Electronic and Optical Properties
journal, January 2016
- Zheng, Tianyue; Cai, Zhengxu; Ho-Wu, Rosina
- Journal of the American Chemical Society, Vol. 138, Issue 3
Naphthalene Diimide-Based Polymer Semiconductors: Synthesis, Structure–Property Correlations, and n-Channel and Ambipolar Field-Effect Transistors
journal, April 2012
- Guo, Xugang; Kim, Felix Sunjoo; Seger, Mark J.
- Chemistry of Materials, Vol. 24, Issue 8
Non-fullerene polymer solar cells based on a selenophene-containing fused-ring acceptor with photovoltaic performance of 8.6%
journal, January 2016
- Li, Yongxi; Zhong, Lian; Wu, Fu-Peng
- Energy & Environmental Science, Vol. 9, Issue 11
Influence of Alkyl Chain Branching Positions on the Hole Mobilities of Polymer Thin-Film Transistors
journal, September 2012
- Lei, Ting; Dou, Jin-Hu; Pei, Jian
- Advanced Materials, Vol. 24, Issue 48
Side-Chain Effect on Cyclopentadithiophene/Fluorobenzothiadiazole-Based Low Band Gap Polymers and Their Applications for Polymer Solar Cells
journal, June 2013
- Li, Yongxi; Zou, Jingyu; Yip, Hin-Lap
- Macromolecules, Vol. 46, Issue 14
Donor–acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells
journal, January 2015
- Wu, Jhong-Sian; Cheng, Sheng-Wen; Cheng, Yen-Ju
- Chemical Society Reviews, Vol. 44, Issue 5
Pyrene-Based Materials for Organic Electronics
journal, November 2011
- Figueira-Duarte, Teresa M.; Müllen, Klaus
- Chemical Reviews, Vol. 111, Issue 11
Molecular origin of high field-effect mobility in an indacenodithiophene–benzothiadiazole copolymer
journal, July 2013
- Zhang, Xinran; Bronstein, Hugo; Kronemeijer, Auke J.
- Nature Communications, Vol. 4, Issue 1
An Electron-Deficient Building Block Based on the B←N Unit: An Electron Acceptor for All-Polymer Solar Cells
journal, December 2015
- Dou, Chuandong; Long, Xiaojing; Ding, Zicheng
- Angewandte Chemie International Edition, Vol. 55, Issue 4
Ladder‐type Heteroarenes: Up to 15 Rings with Five Imide Groups
journal, June 2017
- Wang, Yingfeng; Guo, Han; Ling, Shaohua
- Angewandte Chemie, Vol. 129, Issue 33
A Thienoisoindigo-Naphthalene Polymer with Ultrahigh Mobility of 14.4 cm 2 /V·s That Substantially Exceeds Benchmark Values for Amorphous Silicon Semiconductors
journal, June 2014
- Kim, Gyoungsik; Kang, Seok-Ju; Dutta, Gitish K.
- Journal of the American Chemical Society, Vol. 136, Issue 26
Conjugated Polymer-Based Organic Solar Cells
journal, April 2007
- Günes, Serap; Neugebauer, Helmut; Sariciftci, Niyazi Serdar
- Chemical Reviews, Vol. 107, Issue 4, p. 1324-1338
New Organic Semiconductors with Imide/Amide-Containing Molecular Systems
journal, March 2014
- Liu, Zitong; Zhang, Guanxin; Cai, Zhengxu
- Advanced Materials, Vol. 26, Issue 40
Marked Consequences of Systematic Oligothiophene Catenation in Thieno[3,4- c ]pyrrole-4,6-dione and Bithiopheneimide Photovoltaic Copolymers
journal, September 2015
- Zhou, Nanjia; Guo, Xugang; Ortiz, Rocio Ponce
- Journal of the American Chemical Society, Vol. 137, Issue 39
Strong Electron-Deficient Polymers Lead to High Electron Mobility in Air and Their Morphology-Dependent Transport Behaviors
journal, June 2016
- Zheng, Yu-Qing; Lei, Ting; Dou, Jin-Hu
- Advanced Materials, Vol. 28, Issue 33
Imide- and Amide-Functionalized Polymer Semiconductors
journal, September 2014
- Guo, Xugang; Facchetti, Antonio; Marks, Tobin J.
- Chemical Reviews, Vol. 114, Issue 18
A fused-ring based electron acceptor for efficient non-fullerene polymer solar cells with small HOMO offset
journal, September 2016
- Li, Yongxi; Qian, Deping; Zhong, Lian
- Nano Energy, Vol. 27
Side-Chain-Induced Rigid Backbone Organization of Polymer Semiconductors through Semifluoroalkyl Side Chains
journal, January 2016
- Kang, Boseok; Kim, Ran; Lee, Seon Baek
- Journal of the American Chemical Society, Vol. 138, Issue 11
Dithienylbenzodiimide: a new electron-deficient unit for n-type polymer semiconductors
journal, January 2017
- Chen, Jianhua; Zhang, Xianhe; Wang, Gang
- Journal of Materials Chemistry C, Vol. 5, Issue 37
Ladder-type Heteroarenes: Up to 15 Rings with Five Imide Groups
journal, June 2017
- Wang, Yingfeng; Guo, Han; Ling, Shaohua
- Angewandte Chemie International Edition, Vol. 56, Issue 33
A pentacyclic aromatic lactam building block for efficient polymer solar cells
journal, January 2013
- Cao, Jiamin; Liao, Qiaogan; Du, Xiaoyan
- Energy & Environmental Science, Vol. 6, Issue 11
Thiophene- S , S -dioxidized Indophenine: A Quinoid-Type Building Block with High Electron Affinity for Constructing n-Type Polymer Semiconductors with Narrow Band Gaps
journal, February 2016
- Deng, Yunfeng; Sun, Bin; He, Yinghui
- Angewandte Chemie, Vol. 128, Issue 10
Developing Conjugated Polymers with High Electron Affinity by Replacing a CC Unit with a B ← N Unit
journal, February 2015
- Dou, Chuandong; Ding, Zicheng; Zhang, Zijian
- Angewandte Chemie, Vol. 127, Issue 12
Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding
journal, December 2015
- Yao, Jingjing; Yu, Chenmin; Liu, Zitong
- Journal of the American Chemical Society, Vol. 138, Issue 1
Defect-free Naphthalene Diimide Bithiophene Copolymers with Controlled Molar Mass and High Performance via Direct Arylation Polycondensation
journal, May 2015
- Matsidik, Rukiya; Komber, Hartmut; Luzio, Alessandro
- Journal of the American Chemical Society, Vol. 137, Issue 20
A stable solution-processed polymer semiconductor with record high-mobility for printed transistors
journal, October 2012
- Li, Jun; Zhao, Yan; Tan, Huei Shuan
- Scientific Reports, Vol. 2, Issue 1
Multifluorination toward High-Mobility Ambipolar and Unipolar n-Type Donor-Acceptor Conjugated Polymers Based on Isoindigo
journal, February 2017
- Gao, Yao; Deng, Yunfeng; Tian, Hongkun
- Advanced Materials, Vol. 29, Issue 13
Advances in Charge Carrier Mobilities of Semiconducting Polymers Used in Organic Transistors
journal, September 2013
- Holliday, Sarah; Donaghey, Jenny E.; McCulloch, Iain
- Chemistry of Materials, Vol. 26, Issue 1
High-Performance, Air-Stable Field-Effect Transistors Based on Heteroatom-Substituted Naphthalenediimide-Benzothiadiazole Copolymers Exhibiting Ultrahigh Electron Mobility up to 8.5 cm V −1 s −1
journal, December 2016
- Zhao, Zhiyuan; Yin, Zhihong; Chen, Huajie
- Advanced Materials, Vol. 29, Issue 4
A Model Oligomer Approach to Light-Emitting Semiconducting Polymers
journal, March 1999
- Van Hutten, Paul F.; Krasnikov, Victor V.; Hadziioannou, Georges
- Accounts of Chemical Research, Vol. 32, Issue 3
Tetraazabenzodifluoranthene Diimides: Building Blocks for Solution-Processable n-Type Organic Semiconductors
journal, April 2013
- Li, Haiyan; Kim, Felix Sunjoo; Ren, Guoqiang
- Angewandte Chemie International Edition, Vol. 52, Issue 21, p. 5513-5517
Eleven-Membered Fused-Ring Low Band-Gap Polymer with Enhanced Charge Carrier Mobility and Photovoltaic Performance
journal, March 2014
- Li, Yongxi; Yao, Kai; Yip, Hin-Lap
- Advanced Functional Materials, Vol. 24, Issue 23
n-Channel Polymers by Design: Optimizing the Interplay of Solubilizing Substituents, Crystal Packing, and Field-Effect Transistor Characteristics in Polymeric Bithiophene-Imide Semiconductors
journal, July 2008
- Letizia, Joseph A.; Salata, Michael R.; Tribout, Caitlin M.
- Journal of the American Chemical Society, Vol. 130, Issue 30, p. 9679-9694
Design, Synthesis, and Structure–Property Relationships of Isoindigo-Based Conjugated Polymers
journal, February 2014
- Lei, Ting; Wang, Jie-Yu; Pei, Jian
- Accounts of Chemical Research, Vol. 47, Issue 4
Thiophene- S , S -dioxidized Indophenine: A Quinoid-Type Building Block with High Electron Affinity for Constructing n-Type Polymer Semiconductors with Narrow Band Gaps
journal, February 2016
- Deng, Yunfeng; Sun, Bin; He, Yinghui
- Angewandte Chemie International Edition, Vol. 55, Issue 10
High-mobility Ambipolar Transistors and High-gain Inverters from a Donor-Acceptor Copolymer Semiconductor
journal, January 2010
- Kim, Felix Sunjoo; Guo, Xugang; Watson, Mark D.
- Advanced Materials, Vol. 22, Issue 4, p. 478-482
Indacenodithiophene: a promising building block for high performance polymer solar cells
journal, January 2017
- Li, Yongxi; Gu, Minchao; Pan, Zhe
- Journal of Materials Chemistry A, Vol. 5, Issue 22
Developing Conjugated Polymers with High Electron Affinity by Replacing a CC Unit with a B ← N Unit
journal, February 2015
- Dou, Chuandong; Ding, Zicheng; Zhang, Zijian
- Angewandte Chemie International Edition, Vol. 54, Issue 12
n-Channel Semiconductor Materials Design for Organic Complementary Circuits
journal, July 2011
- Usta, Hakan; Facchetti, Antonio; Marks, Tobin J.
- Accounts of Chemical Research, Vol. 44, Issue 7, p. 501-510
25th Anniversary Article: Key Points for High-Mobility Organic Field-Effect Transistors
journal, September 2013
- Dong, Huanli; Fu, Xiaolong; Liu, Jie
- Advanced Materials, Vol. 25, Issue 43
25th Anniversary Article: Recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors
journal, August 2013
- Zhao, Yan; Guo, Yunlong; Liu, Yunqi
- Advanced Materials, Vol. 25, Issue 38
Strategies for the Synthesis of Functional Naphthalene Diimides
journal, June 2014
- Suraru, Sabin-Lucian; Würthner, Frank
- Angewandte Chemie International Edition, Vol. 53, Issue 29
Biazulene diimides: a new building block for organic electronic materials
journal, January 2016
- Xin, Hanshen; Ge, Congwu; Yang, Xiaodi
- Chemical Science, Vol. 7, Issue 11
Non-fullerene acceptor with low energy loss and high external quantum efficiency: towards high performance polymer solar cells
journal, January 2016
- Li, Yongxi; Liu, Xiaodong; Wu, Fu-Peng
- Journal of Materials Chemistry A, Vol. 4, Issue 16
Organische Halbleiter für aus Lösung prozessierbare Feldeffekttransistoren
journal, May 2008
- Allard, Sybille; Forster, Michael; Souharce, Benjamin
- Angewandte Chemie, Vol. 120, Issue 22
Record High Hole Mobility in Polymer Semiconductors via Side-Chain Engineering
journal, September 2013
- Kang, Il; Yun, Hui-Jun; Chung, Dae Sung
- Journal of the American Chemical Society, Vol. 135, Issue 40
Synthesis, Characterization, and Photovoltaic Properties of Novel Semiconducting Polymers with Thiophene−Phenylene−Thiophene (TPT) as Coplanar Units
journal, August 2008
- Chan, Shu-Hua; Chen, Chih-Ping; Chao, Teng-Chih
- Macromolecules, Vol. 41, Issue 15
Dithienylthienothiophenebisimide, a Versatile Electron-Deficient Unit for Semiconducting Polymers
journal, May 2016
- Saito, Masahiko; Osaka, Itaru; Suda, Yosuke
- Advanced Materials, Vol. 28, Issue 32
An Electron-Deficient Building Block Based on the B←N Unit: An Electron Acceptor for All-Polymer Solar Cells
journal, December 2015
- Dou, Chuandong; Long, Xiaojing; Ding, Zicheng
- Angewandte Chemie, Vol. 128, Issue 4
Tetraazabenzodifluoranthene Diimides: Building Blocks for Solution-Processable n-Type Organic Semiconductors
journal, April 2013
- Li, Haiyan; Kim, Felix Sunjoo; Ren, Guoqiang
- Angewandte Chemie, Vol. 125, Issue 21
Thieno[3,4- c ]pyrrole-4,6-dione-Based Donor−Acceptor Conjugated Polymers for Solar Cells
journal, January 2011
- Guo, Xugang; Xin, Hao; Kim, Felix Sunjoo
- Macromolecules, Vol. 44, Issue 2
Fluoro-benzoselenadiazole-based low band gap polymers for high efficiency organic solar cells
journal, January 2014
- Li, Yongxi; Pan, Zhe; Miao, Lei
- Polym. Chem., Vol. 5, Issue 2
Organic Semiconductors for Solution-Processable Field-Effect Transistors (OFETs)
journal, May 2008
- Allard, Sybille; Forster, Michael; Souharce, Benjamin
- Angewandte Chemie International Edition, Vol. 47, Issue 22
Asymmetric Diketopyrrolopyrrole Conjugated Polymers for Field-Effect Transistors and Polymer Solar Cells Processed from a Nonchlorinated Solvent
journal, November 2015
- Ji, Yunjing; Xiao, Chengyi; Wang, Qiang
- Advanced Materials, Vol. 28, Issue 5
Conjugated Polymer-Based Organic Solar Cells
journal, July 2007
- Guenes, Serap; Neugebauer, Helmut; Sariciftci, Niyazi Serdar
- ChemInform, Vol. 38, Issue 31
Works referencing / citing this record:
Imide‐Functionalized Polymer Semiconductors
journal, December 2018
- Sun, Huiliang; Wang, Lei; Wang, Yingfeng
- Chemistry – A European Journal, Vol. 25, Issue 1
Synthesis and characterization of new N-{4,6-bis[2-(het)arylvinyl]pyrimidin-2-yl}-substituted polycyclic aromatic imides
journal, September 2019
- Komissarova, E. A.; Vasyanin, A. N.; Zhulanov, V. E.
- Russian Chemical Bulletin, Vol. 68, Issue 9
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