A novel donor-acceptor molecule containing a cyclic triphenylamine dimer: synthesis, characterization, and application in memory device

被引：17
作者：
Zhao, Yun [1 ,2 ]
Ye, Changqing [1 ,2 ]
Qiao, Yali [1 ,2 ]
Xu, Wei [1 ]
Song, Yanlin [1 ]
Zhu, Daoben [1 ]
机构：
[1] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
[2] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Organ Solids Lab, Beijing 100190, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 05期
关键词：
PHOTOINDUCED ELECTRON-TRANSFER; THIN-FILM; POLYMER; TRANSISTORS; DYAD;
D O I：
10.1016/j.tet.2011.12.007
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel highly soluble push pull molecule containing electron-rich cyclic triphenylamine dimer (TPAD) and electron-poor N-phenyl-N'-octyl-naphthalene-1,4,5,8-tetracarboxylic acid bisimide [NI-(8,PBr)] was synthesized under Suzuki-coupling conditions. The resulting compound exhibited excellent thermal stability (T-d=354.3 degrees C) and good solubility in common organic solvents. Cyclic voltammogram and optical absorption spectroscopy showed that both the electroactive units preserve their nature, respectively, in the ground state, whereas photophysical investigations showed a strong fluorescence quenching. Interestingly, excellent switching behavior with extremely high ON/OFF current ratio (1.6E8 at +1 V) was observed through memory devices based on thin films of this material. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1547 / 1551
页数：5
相关论文
共 26 条
  • [21] Synthesis, characterization and comparative study of thiophene-benzothiadiazole based donor-acceptor-donor (D-A-D) materials
    Sonar, Prashant
    Singh, Samarendra P.
    Leclere, Philippe
    Surin, Mathieu
    Lazzaroni, Roberto
    Lin, Ting Ting
    Dodabalapur, Ananth
    Sellinger, Alan
    [J]. JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (20) : 3228 - 3237
  • [22] A cyclic triphenylamine dimer for organic field-effect transistors with high performance
    Song, Yabin
    Di, Chong'an
    Yang, Xiaodi
    Li, Shouping
    Xu, Wei
    Liu, Yunqi
    Yang, Lianming
    Shuai, Zhigang
    Zhang, Deqing
    Zhu, Daoben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) : 15940 - 15941
  • [23] ORGANIC ELECTROLUMINESCENT DIODES
    TANG, CW
    VANSLYKE, SA
    [J]. APPLIED PHYSICS LETTERS, 1987, 51 (12) : 913 - 915
  • [24] Ultrafast photoinduced electron transfer in a chlorophyll-based triad: Vibrationally hot ion pair intermediates and dynamic solvent effects
    Wiederrecht, GP
    Niemczyk, MP
    Svec, WA
    Wasielewski, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) : 81 - 88
  • [25] Electrical switching and bistability in organic/polymeric thin films and memory devices
    Yang, Yang
    Ouyang, Jianyong
    Ma, Liping
    Tseng, Ricky Jia-Hung
    Chu, Chih-Wei
    [J]. ADVANCED FUNCTIONAL MATERIALS, 2006, 16 (08) : 1001 - 1014
  • [26] Polyfluorene-Based Push-Pull Type Functional Materials for Write-Once-Read-Many-Times Memory Devices
    Zhuang, Xiao-Dong
    Chen, Yu
    Li, Bi-Xin
    Ma, Dong-Ge
    Zhang, Bin
    Li, Yongxi
    [J]. CHEMISTRY OF MATERIALS, 2010, 22 (15) : 4455 - 4461
123