ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img
RETURN TO ISSUEPREVOrganic Electronic D...Organic Electronic DevicesNEXT

Effect of Alkyl Chain Length on Charge Transport Property of Anthracene-Based Organic Semiconductors

  • Dongwei Zhang*
    Dongwei Zhang
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    *Email: [email protected]
  • So Yokomori
    So Yokomori
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    More by So Yokomori
  • Ryohei Kameyama
    Ryohei Kameyama
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
  • Changbin Zhao
    Changbin Zhao
    School of Advanced Materials, Peking University Shenzhen Graduate School, Peking University, Shenzhen 518055, China
  • Akira Ueda
    Akira Ueda
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    Department of Chemistry, Faculty of Advanced Science and Technology, Kumamoto University, 2-39-1 Kurokami, Chuo-ku, Kumamoto 860-8555, Japan
    More by Akira Ueda
  • Lei Zhang
    Lei Zhang
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    More by Lei Zhang
  • Reiji Kumai
    Reiji Kumai
    Condensed Matter Research Center (CMRC) and Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), Tsukuba, Ibaraki 3050801, Japan
    More by Reiji Kumai
  • Youichi Murakami
    Youichi Murakami
    Condensed Matter Research Center (CMRC) and Photon Factory, Institute of Materials Structure Science, High Energy Accelerator Research Organization (KEK), Tsukuba, Ibaraki 3050801, Japan
  • Hong Meng
    Hong Meng
    School of Advanced Materials, Peking University Shenzhen Graduate School, Peking University, Shenzhen 518055, China
    More by Hong Meng
  • , and 
  • Hatsumi Mori*
    Hatsumi Mori
    The Institute for Solid State Physics, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8581, Japan
    *Email: [email protected]
    More by Hatsumi Mori
Cite this: ACS Appl. Mater. Interfaces 2021, 13, 1, 989–998
Publication Date (Web):December 17, 2020
https://doi.org/10.1021/acsami.0c16144
Copyright © 2020 American Chemical Society

    Article Views

    1811

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (3)»

    Abstract

    Abstract Image

    Anthracene, a simple planar building block for organic semiconductors, shows strong intermolecular interactions and exhibits strong blue fluorescence. Thus, its derivatives have a great potential to integrate considerable charge carrier mobility and strong emission within a molecule. Here, we systematically studied the influence of alkyl chain length on the crystal structures, thermal properties, photophysical characteristics, electrochemical behaviors, and mobilities for a series of 2,6-di(4-alkyl-phenyl)anthracenes (Cn-Ph-Ants, where n represents the alkyl chain length). Among them, Cn-Ph-Ants (n = 0, 1, 2, and 3) display similar layered herringbone (LHB) packing motifs, which facilitate two-dimensional charge transport and thereby enables high-performance organic field-effect transistors (OFETs). All Cn-Ph-Ants exhibit similar work functions and show strong blue fluorescence with photoluminescence quantum yields (PLQY) of approximately 40% in toluene. In addition, the absolute powder PLQYs of C0-, C2-, C3-, C4-, and C6-Ph-Ants are 24.6, 8.2, 5.7, 10.9, and 8.6%, respectively. Note that the alkyl chain length shows a significant effect on the charge mobilities of Cn-Ph-Ants. Our newly synthesized C1-, C3-, and C4-Ph-Ants show hole mobilities of up to 2.40, 1.34, and 1.00 cm2 V–1 s–1, respectively, with mobilities of 3.40, 1.57, and 0.82 cm2 V–1 s–1 for C0-, C2-, and C6-Ph-Ants, indicating an increasing tendency of mobility with shorter alkyl chain length. This feature is related to the microstructures of the thin films, which reveal the enhanced film order, crystallinity, and grain size with a decrease in the alkyl chain length. Moreover, we theoretically analyze the intermolecular transfer integrals of HOMOs, which increase at T-shaped contacts as the alkyl chain length decreases, which improves the intermolecular charge transport properties, leading to the increases in mobility. Interestingly, the anisotropy of the transfer integral tends to decrease upon substitution with longer alkyl chains, suggesting that alkyl chain adjustments may facilitate isotropic charge transport property in 2,6-alkylated anthracenes.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsami.0c16144.

    • Crystallographic data of C1-Ph-Ant (CIF)

    • Crystallographic data of C3-Ph-Ant (CIF)

    • General experimental method; synthesis routes; chemicophysical characterizations, including 1H and 13C NMR spectroscopy and elemental analysis; powder X-ray pattern; molecular packing structures and parameters; Hirshfeld surfaces and fingerprint plots; hysteresis of transfer curves; output transfer characteristics; effects of self-assembled monolayers and annealing on mobility, transfer integral and calculated angular resolution mobility; and DSC, TGA, and PLQY measurements (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 17 publications.

    1. Zhongwei Liu, Ting Jiang, Yanru Li, Yunpeng Lou, Chan Zhang, Jie Li, Yajing Sun, Xing Chen, Liqiang Li, Hongkun Tian, Deyang Ji, Zhuping Fei. Modulating the Alkylation Position on Terminal Thiophene Ring of Naphtho[2,3-b:6,7-b′] Bithieno[2,3-d] Thiophene (NBTT) for High-Performance Organic Optoelectronic Devices. ACS Applied Materials & Interfaces 2023, 15 (13) , 16930-16941. https://doi.org/10.1021/acsami.3c02547
    2. Soraya Rahpeima, Essam M. Dief, Simone Ciampi, Colin L. Raston, Nadim Darwish. Impermeable Graphene Oxide Protects Silicon from Oxidation. ACS Applied Materials & Interfaces 2021, 13 (32) , 38799-38807. https://doi.org/10.1021/acsami.1c06495
    3. Dongwei Zhang, Xiwei Zheng, Chao He, Yaowu He, Hong Meng. Enhanced performance in doped micro-nano porous organic thin-film transistors. Applied Physics Letters 2024, 124 (12) https://doi.org/10.1063/5.0193504
    4. Ranjan Kumar, Nidhi Sinha, Binay Kumar. Results and analysis of changes in structural, Raman and luminescence properties in anthracene crystals by divalent metal ions doping. Journal of Materials Science: Materials in Electronics 2024, 35 (9) https://doi.org/10.1007/s10854-024-12374-1
    5. Maowei Qi, Dongwei Zhang, Yanan Zhu, Changbin Zhao, Aiyuan Li, Fobao Huang, Yaowu He, Hong Meng. Anthracene-[1]benzothieno[3,2- b ][1]benzothiophene (BTBT) dyad and triads as p-type semiconductors for organic field-effect transistors and phototransistors. Journal of Materials Chemistry C 2024, 25 https://doi.org/10.1039/D4TC00251B
    6. Chengjian Li, Qing Zhang, Jingwei Sun, Kai Wang, Mi Ouyang, Yujian Zhang. A rigid-flexible steric blocking strategy for highly bright and ultrawide piezochromism in the deep-red/near-infrared region. Journal of Materials Chemistry C 2023, 11 (45) , 16017-16025. https://doi.org/10.1039/D3TC03109H
    7. Junhwan Choi, Min Ju Kim, Joo‐Young Kim, Eun Kyung Lee, Changhyeon Lee, Youngkeun Park, Juyeon Kang, Jeong‐Il Park, Byung Jin Cho, Sung Gap Im. The Effect of Alkyl Chain Length in Organic Semiconductor and Surface Polarity of Polymer Dielectrics in Organic Thin‐Film Transistors (OTFTs). Small Methods 2023, 7 (11) https://doi.org/10.1002/smtd.202300628
    8. Dongwei Zhang, Changbin Zhao, Xiwei Zheng, Lijie Wu, Jinhao Xu, Liguo Zhou, Ping Kwan Johnny Wong, Wen Zhang, Yaowu He. A study on the luminescence properties of high-performance benzothieno[3,2-b][1]benzothiophene based organic semiconductors. Dyes and Pigments 2023, 216 , 111359. https://doi.org/10.1016/j.dyepig.2023.111359
    9. Jiayao Duan, Jiamin Ding, Dongyang Wang, Xiuyuan Zhu, Junxin Chen, Genming Zhu, Chaoyue Chen, Yaping Yu, Hailiang Liao, Zhengke Li, Chong‐an Di, Wan Yue. Enhancing the Performance of N‐Type Thermoelectric Devices via Tuning the Crystallinity of Small Molecule Semiconductors. Advanced Science 2023, 10 (3) https://doi.org/10.1002/advs.202204872
    10. Guiya Qin, Panpan Lin, Xiaoqi Sun, Jingfu Guo, Jianxun Fan, Lifei Ji, Hui Li, Aimin Ren. Theoretically seeking charge transport materials with inherent mobility higher than 2,6-diphenyl anthracene: three isomers of 2,6-dipyridyl anthracene. Physical Chemistry Chemical Physics 2022, 25 (1) , 540-554. https://doi.org/10.1039/D2CP03926E
    11. Dongwei Zhang, Liguo Zhou, Ping Kwan Johnny Wong, Wen Zhang. Insight into the effect of alkyl chain length and substituent bulkiness on the mobility anisotropy of benzothieno[3,2- b ][1]benzothiophenes. Journal of Materials Chemistry C 2022, 10 (48) , 18423-18432. https://doi.org/10.1039/D2TC03721A
    12. Youngseok Kim, Chaeyoung Yun, Seungjae Yun, Dongil Ho, Taeshik Earmme, Choongik Kim, SungYong Seo. Modification of alkyl side chain on thiophene-containing benzothieno[3,2-b]benzothiophene-based organic semiconductors for organic field-effect transistors. Synthetic Metals 2022, 291 , 117173. https://doi.org/10.1016/j.synthmet.2022.117173
    13. Dan Zhou, Hehui Zhang, Haolan Zheng, Zhentian Xu, Haitao Xu, Huilong Guo, Peining Li, Yongfen Tong, Bin Hu, Lie Chen. Recent Advances and Prospects of Small Molecular Organic Thermoelectric Materials. Small 2022, 18 (23) https://doi.org/10.1002/smll.202200679
    14. Yan Zhao, Shuo‐Hui Cao, Jia‐Dai Wang, Na Li, Guo‐Chun Lin, Yao‐Qun Li. Polarization‐ and Angle‐Dependent Plasmonic Synchronous Fluorescence Spectroscopy to Probe Molecular Vibrational Couplings on an Aluminum Nano‐Film. Advanced Optical Materials 2022, 10 (8) https://doi.org/10.1002/adom.202101973
    15. Miki Murakami, Kazuya Maeda, Hajime Maeda, Masahito Segi, Taniyuki Furuyama. Synthesis of V-shaped fused phthalonitriles and control of their molecular orientation. Tetrahedron Letters 2022, 95 , 153750. https://doi.org/10.1016/j.tetlet.2022.153750
    16. Yongchul Lee, Soomin Ryu, Eunjin Choi, Dongil Ho, Taeshik Earmme, Choongik Kim, SungYong Seo. Synthesis and characterization of benzo[b]thieno[2,3-d]thiophene (BTT) derivatives as solution-processable organic semiconductors for organic field-effect transistors. Synthetic Metals 2021, 282 , 116944. https://doi.org/10.1016/j.synthmet.2021.116944
    17. Kalyan Jyoti Kalita, Indrajit Giri, Ratheesh K. Vijayaraghavan. Influence of non-covalent interactions in dictating the polarity and mobility of charge carriers in a series of crystalline NDIs: a computational case study. RSC Advances 2021, 11 (53) , 33703-33713. https://doi.org/10.1039/D1RA05274H

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect