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Title: An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors

Abstract

For this study 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) (-6.24 eV) and the lowest unoccupied molecular orbit (LUMO) (-2.57 eV) energy levels. Organic field-effect transistors (OFETs) based on BBI polymers exhibit electron mobility up to 0.34 cm 2 V -1 s -1, which indicates that the BBI is a promising n-type building block for optoelectronics.

Authors:
 [1];  [2]; ORCiD logo [1];  [1];  [1];  [3];  [3];  [4];  [2];  [1];  [2];  [1]
  1. Soochow Univ., Suzhou (China). Inst. of Functional Nano & Soft Materials (FUNSOM)
  2. 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
  3. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS)
  4. Argonne National Lab. (ANL), Lemont, IL (United States). Science Div.
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Argonne National Lab. (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 (NNSFC)
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. 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, and Liao, Liang-Sheng. Mon . "An Imide-Based Pentacyclic Building Block for n-Type Organic Semiconductors". United States. doi: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 = {For this study 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) (-6.24 eV) and the lowest unoccupied molecular orbit (LUMO) (-2.57 eV) 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 n-type building block for optoelectronics.},
doi = {10.1002/chem.201703415},
journal = {Chemistry - A European Journal},
number = 59,
volume = 23,
place = {United States},
year = {2017},
month = {10}
}

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Cited by: 2 works
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Figures / Tables:

Figure 1 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 referencing / citing this record:

    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
    • DOI: 10.1002/adfm.201303953

    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
    • DOI: 10.1002/adma.200901819

    Influence of Alkyl Chain Branching Positions on the Hole Mobilities of Polymer Thin-Film Transistors
    journal, September 2012


    25th Anniversary Article: Recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors
    journal, August 2013


    25th Anniversary Article: Key Points for High-Mobility Organic Field-Effect Transistors
    journal, September 2013


    New Organic Semiconductors with Imide/Amide-Containing Molecular Systems
    journal, March 2014


    Strong Electron-Deficient Polymers Lead to High Electron Mobility in Air and Their Morphology-Dependent Transport Behaviors
    journal, June 2016


    Dithienylthienothiophenebisimide, a Versatile Electron-Deficient Unit for Semiconducting Polymers
    journal, May 2016

    • Saito, Masahiko; Osaka, Itaru; Suda, Yosuke
    • Advanced Materials, Vol. 28, Issue 32
    • DOI: 10.1002/adma.201601373

    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
    • DOI: 10.1002/adma.201602598

    Multifluorination toward High-Mobility Ambipolar and Unipolar n-Type Donor-Acceptor Conjugated Polymers Based on Isoindigo
    journal, February 2017


    Organische Halbleiter für aus Lösung prozessierbare Feldeffekttransistoren
    journal, May 2008

    • Allard, Sybille; Forster, Michael; Souharce, Benjamin
    • Angewandte Chemie, Vol. 120, Issue 22
    • DOI: 10.1002/ange.200701920

    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
    • DOI: 10.1002/ange.201210085

    Strategien für die Synthese funktioneller Naphthalindiimide
    journal, June 2014


    Developing Conjugated Polymers with High Electron Affinity by Replacing a CC Unit with a B N Unit
    journal, February 2015

    • Dou, Chuandong; Ding, Zicheng; Zhang, Zijian
    • Angewandte Chemie, Vol. 127, Issue 12
    • DOI: 10.1002/ange.201411973

    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
    • DOI: 10.1002/ange.201508482

    Ladder‐type Heteroarenes: Up to 15 Rings with Five Imide Groups
    journal, June 2017


    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
    • DOI: 10.1002/anie.200701920

    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
    • DOI: 10.1002/anie.201210085

    Strategies for the Synthesis of Functional Naphthalene Diimides
    journal, June 2014

    • Suraru, Sabin-Lucian; Würthner, Frank
    • Angewandte Chemie International Edition, Vol. 53, Issue 29
    • DOI: 10.1002/anie.201309746

    Developing Conjugated Polymers with High Electron Affinity by Replacing a CC Unit with a B N Unit
    journal, February 2015

    • Dou, Chuandong; Ding, Zicheng; Zhang, Zijian
    • Angewandte Chemie International Edition, Vol. 54, Issue 12
    • DOI: 10.1002/anie.201411973

    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
    • DOI: 10.1002/anie.201508482

    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
    • DOI: 10.1002/anie.201508781

    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
    • DOI: 10.1002/anie.201702225

    A fused-ring based electron acceptor for efficient non-fullerene polymer solar cells with small HOMO offset
    journal, September 2016


    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
    • DOI: 10.1021/ar200006r

    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
    • DOI: 10.1021/ar400254j

    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
    • DOI: 10.1021/ar980032f

    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
    • DOI: 10.1021/cm2034273

    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
    • DOI: 10.1021/cm402421p

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      Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.