One-Pot Synthesis of Core-Expanded Naphthalene Diimides: Enabling N-Substituent Modulation for Diverse n-Type Organic Materials

被引:61
作者
Hu, Yunbin [1 ]
Qin, Yunke [1 ]
Gao, Xike [1 ]
Zhang, Fengjiao [2 ]
Di, Chong-an [2 ]
Zhao, Zheng [1 ]
Li, Hongxiang [1 ]
Zhu, Daoben [1 ,2 ]
机构
[1] Chinese Acad Sci CAS, Shanghai Inst Organ Chem, Mat Sci Lab, Shanghai 200032, Peoples R China
[2] CAS, Key Lab Organ Solids, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
关键词
THIN-FILM TRANSISTORS; HIGH-ELECTRON-MOBILITY; HIGH-PERFORMANCE; OPTICAL-PROPERTIES; PERYLENE DIIMIDES; MATERIALS DESIGN; SEMICONDUCTORS; DERIVATIVES; CIRCUITS; DYES;
D O I
10.1021/ol203059r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and versatile one-pot synthesis of core-expanded naphthalene dilmides has been developed, which undergoes a nucleophilic aromatic substitution reaction and then an imidization reaction, allowing an easy and low-cost access to diverse n-type organic materials. Some newly synthesized compounds by this one-pot operation exhibited high electron mobility of up to 0.70 cm(2) V-1 s(-1) in ambient conditions.
引用
收藏
页码:292 / 295
页数:4
相关论文
共 10 条
  • [1] New Core-Expanded Naphthalene Diimides for n-Channel Organic Thin Film Transistors
    Hu, Yunbin
    Wang, Zhongli
    Zhang, Xu
    Yang, Xiaodi
    Li, Hongxiang
    Gao, Xike
    CHINESE JOURNAL OF CHEMISTRY, 2013, 31 (11) : 1428 - 1438
  • [2] Selenium-containing core-expanded naphthalene diimides for high performance n-type organic semiconductors
    Han, Wenjie
    Wang, Zhongli
    Hu, Yunbin
    Yang, Xiaodi
    Ge, Congwu
    Gao, Xike
    SCIENCE CHINA-CHEMISTRY, 2020, 63 (09) : 1182 - 1190
  • [3] New core-expanded naphthalene diimides with different functional groups for air-stable solution-processed organic n-type semiconductors
    Chen, Xin
    Wang, Jianguo
    Zhang, Guanxin
    Liu, Zitong
    Xu, Wei
    Zhang, Deqing
    NEW JOURNAL OF CHEMISTRY, 2013, 37 (06) : 1720 - 1727
  • [4] New air-stable solution-processed organic n-type semiconductors based on sulfur-rich core-expanded naphthalene diimides
    Tan, Luxi
    Guo, Yunlong
    Zhang, Guanxin
    Yang, Yang
    Zhang, Deqing
    Yu, Gui
    Xu, Wei
    Liu, Yunqi
    JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (44) : 18042 - 18048
  • [5] One-Pot Domino Carbonylation Protocol for Aromatic Diimides toward n-Type Organic Semiconductors
    Fu, Xiaolong
    Zhen, Yonggang
    Ni, Zhenjie
    Li, Yang
    Dong, Huanli
    Siegel, Jay S.
    Hu, Wenping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (33) : 14024 - 14028
  • [6] Core-Fluorinated Naphthalene Diimides: Synthesis, Characterization, and Application in n-Type Organic Field-Effect Transistors
    yuan, Zhongyi
    Ma, Yingjie
    Gessner, Thomas
    Li, Mengmeng
    Chen, Long
    Eustachi, Michael
    Weitz, R. Thomas
    Li, Chen
    Muellen, Klaus
    ORGANIC LETTERS, 2016, 18 (03) : 456 - 459
  • [7] Solution-processed core-extended naphthalene diimides toward organic n-type and ambipolar semiconductors
    Luo, Hewei
    Cai, Zhengxu
    Tan, Luxi
    Guo, Yunlong
    Yang, Ge
    Liu, Zitong
    Zhang, Guanxin
    Zhang, Deqing
    Xu, Wei
    Liu, Yunqi
    JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (15) : 2688 - 2695
  • [8] High-Performance Air-Stable n-Type Organic Transistors Based on Core-Chlorinated Naphthalene Tetracarboxylic Diimides
    Oh, Joon Hak
    Suraru, Sabin-Lucian
    Lee, Wen-Ya
    Koenemann, Martin
    Hoeffken, Hans Wolfgang
    Roeger, Cornelia
    Schmidt, Ruediger
    Chung, Yoonyoung
    Chen, Wen-Chang
    Wuerthner, Frank
    Bao, Zhenan
    ADVANCED FUNCTIONAL MATERIALS, 2010, 20 (13) : 2148 - 2156
  • [9] Core-Expanded Naphthalene Diimides Fused with Sulfur Heterocycles and End-Capped with Electron-Withdrawing Groups for Air-Stable Solution-Processed n-Channel Organic Thin Film Transistors
    Hu, Yunbin
    Gao, Xike
    Di, Chong-an
    Yang, Xiaodi
    Zhang, Feng
    Liu, Yunqi
    Li, Hongxiang
    Zhu, Daoben
    CHEMISTRY OF MATERIALS, 2011, 23 (05) : 1204 - 1215
  • [10] Core-Expanded Naphthalene Diimides Fused with 2-(1,3-Dithiol-2-Ylidene)Malonitrile Groups for High-Performance, Ambient-Stable, Solution-Processed n-Channel Organic Thin Film Transistors
    Gao, Xike
    Di, Chong-an
    Hu, Yunbin
    Yang, Xiaodi
    Fan, Hongyu
    Zhang, Feng
    Liu, Yunqi
    Li, Hongxiang
    Zhu, Daoben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3697 - +