Citation: XIAO Lixin, HU Shuangyuan, KONG Sheng, CHEN Zhijian, QU Bo, NG Qihuang. Synthesis of Poly(9,9-diallylfluorene) and the Mechanism of Its Single Green Emission[J]. Acta Physico-Chimica Sinica, ;2011, 27(04): 977-982. doi: 10.3866/PKU.WHXB20110325 shu

Synthesis of Poly(9,9-diallylfluorene) and the Mechanism of Its Single Green Emission

1.
State Key Laboratory for Mesoscopic Physics, School of Physics, Peking University, Beijing 100871, P. R. China

Received Date: 19 November 2010
Available Online: 15 February 2011
Fund Project: 国家自然科学基金(10934001, 60907015, 10821062) (10934001, 60907015, 10821062)国家重点基础研究发展规划项目(973) (2007CB307000, 2009CB930504)资助 (973) (2007CB307000, 2009CB930504)

Poly(9,9-diallylfluorene) (PAF) with single green emission was synthesized through polymerization of allyl substituted 2,7-dibromofluorene in the presence of NiCl₂ as the catalyst. PAF shows deep blue fluorescence at 403 nm in solution and 456 nm in solid film state. The organic electroluminescence device (OLED) gives a green emission with the peak at 532 nm by using PAF as the emitter with a structure of ITO/PEDOT:PSS/PAF/LiF/Al (ITO: indium tin oxides; PEDOT: poly(3,4- ethylenedioxythiophene); PSS: poly(styrenesulfonate)). The photoluminescence (PL) of the PAF film red- shifted after thermal anealing, the original peak of blue emission decreased and a new peak of green emissioin increased. However, there is no change in the chemical structure based on the Fourier transform infrared (FT-IR) spectra of PAF after thermal annealing under vacuum. Moreover, there is no change on the PL spectra of PAF before and after the evaporation of metal cathode. It can be deduced that the single green emisson of PAF based OLED is original from the inter-chain aggregation which can be confirmed from their atomic force microscopy (AFM) images.
- Polymer,
- Diallylfluorene,
- Green emission,
- Inter-chain aggregation,
- Organic light-emitting device
1. [1]
  
  (1) Burroughes, J. H.; Bradleyd, D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
2. [2]
  (2) Cao, H. Y.; Chen, Z. J.; Xiao, L. X.; Liu, Z. G.; Zheng, M. J.; Qu, B.; ng, Q. H. Spectroscopy and Spectra Analysis 2008, 28, 752.
3. [3]
  [曹华雨, 陈志坚, 肖立新, 刘振刚, 郑明杰, 曲波, 龚旗煌. 光谱学与光谱分析, 2008, 28, 752.]
4. [4]
  (3) Ohmori, Y.; Uchida, A.; Muro, K.; Yoshino, K. Jpn. J. Appl. Phys. 1991, 30, L1941.
5. [5]
  (4) Fukuda, K.; Sawaka, K.; Yoshino, J. J. Polym. Sci. Part A: Polym. Chem. 1993, 31, 2465.
6. [6]
  (5) Schluter, A. D. J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 1533.
7. [7]
  (6) Tao, S. L.; Peng, Z. K.; Zhang, X. H.; Wang, P. F.; Lee, C. S.; Lee, S. T. Adv. Funct. Mater. 2005, 15, 1716.
8. [8]
  (7) Gao, Z. Q.; Li, Z. H.; Xia, P. F.; Wong, M. S.; Cheah, K. W.; Chen, C. H. Adv. Funct. Mater. 2007, 17, 3194.
9. [9]
  (8) Wong, K. T.; Chien, Y. Y.; Chen, R. T.; Wang, C. F.; Lin, Y. T.; Chiang, H. H.; Hsieh, P. Y.; Wu, C. C.; Chou, C. H.; Su, Y. O.; Lee, G. H.; Peng, S. M. J. Am. Chem. Soc. 2002, 124, 11576.
10. [10]
  (9) Sun, G. N.; Xu, H.; Liu, X. D.; Liu, D. D.; Yang, B.; Tian, L. L.; Ma, Y. G. Acta Phys. -Chim. Sin. 2010, 26, 2529.
11. [11]
  [孙冠楠, 许海, 刘晓冬, 刘丹丹, 杨兵, 田雷蕾, 马於光. 物理化学学报, 2010, 26, 2529.]
12. [12]
  (10) Ma, T.; Jiang, Y. D.; Yu, J. S.; Lou, S. L.; Li, L.; Zhang, Q. Acta Phys. -Chim. Sin. 2008, 24, 977.
13. [13]
  [马涛, 蒋亚东, 于军胜, 娄双玲, 李璐, 张清. 物理化学学报, 2008, 24, 977.]
14. [14]
  (11) Abbel, R.; Schenning, A. P. H. J.; Meijer, E. W. J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 4215.
15. [15]
  (12) Li, F. S.; Chen, Z. J.; Qu, B.; Wei, W.; ng, Q. H. J. Phys. D: Appl. Phys. 2005, 38, 847.
16. [16]
  (13) Li, Y. B.; Teng, F.; Xu, Z.; Hou, Y. B.; Xu, X. Spectroscopy and Spectra Analysis 2005, 25, 1030.
17. [17]
  [李云白, 滕枫, 徐征, 侯延冰, 徐叙. 光谱学与光谱分析, 2005, 25, 1030.]
18. [18]
  (14) Kreenschmidt, M.; Klarner, G.; Fuhrer, T.; Ashenhurst, J.; Karg, S.; Chen, W. D.; Lee, V. Y.; Scott, J. C.; Miller, R. D. Macromolecules 1998, 31, 1099.
19. [19]
  (15) Kl?rner, G.; Lee, J.; Lee, V. Y.; Chan, E.; Chen, J. P.; Nelson, A.; Markiewicz, D.; Siemens, R.; Scott, J. C.; Miller, R. D. Chem. Mater. 1999, 11, 1800.
20. [20]
  (16) List, J. W.; Guentner, R.; Freitas, P. S.; Scherf, U. Adv. Mater. 2002, 14, 374.
21. [21]
  (17) Grisorio, R.; Suranna, G. P.; Mastrorilli, P.; Nobile, C. F. Adv. Funct. Mater. 2007, 17, 538.
22. [22]
  (18) Chi, C.; Im, C.; Enkelmann, V.; Ziegler, A.; Lieser, G.; Wegner, G. Chem. Eur. J. 2005, 11, 6833.
23. [23]
  (19) Craig, M. R.; Meijer, E. W. Appl. Phys. Lett. 2002, 80, 4489.
24. [24]
  (20) Liang, J.; Qian, Y.; Xie, L. H.; Shi, N. E.; Chen, S. F.; Deng, X. Y.; Huang, W. Acta Phys. -Chim. Sin. 2010, 26, 946.
25. [25]
  [梁婧, 钱妍, 解令海, 石乃恩, 陈淑芬, 邓先宇, 黄维. 物理化学学报, 2010, 26, 946.]
26. [26]
  (21) Zhang, L.; Lin, Z. Q.; Gu, J. F.; Yin, C. R.; Hou, X. Y.; Liu, F.; Liu, Y. Y.; Xie, L. H.; Chen, S. F.; Huang, W. Acta Phys. -Chim. Sin. 2010, 26, 1934.
27. [27]
  [张龙, 林宗琼, 顾菊芬, 殷成蓉, 侯晓雅, 刘烽, 刘玉玉, 解令海, 陈淑芬, 黄维. 物理化学学报, 2010, 26, 1934.]
28. [28]
  (22) Setayesh, S.; Grimsdale, A. C.; Weil, T.; Enkelmann, V.; Mullen, K.; Meghdadi, F.; List, E. J. W.; Leising, G. J. Am. Chem. Soc. 2001, 123, 946.
29. [29]
  (23) Jin, J. K.; Kwon, S. K.; Kim, Y. H.; Shin, D. C.; You, H.; Jung, H. T. Macromolecules 2009, 42, 6339.
30. [30]
  (24) Zhou, X. H.; Zhang, Y.; Xie, Y. Q.; Cao, Y.; Pei, J. Macromolecules 2006, 39, 3830.
31. [31]
  (25) Ranger, M.; Rondeau, D.; Leclerc, M. Macromolecules 1997, 30, 7686.
1. [1]
  Yuxia Luo , Xiaoyu Xie , Fangfang Chen . 药物递送魔法师——分子印迹聚合物. University Chemistry, 2025, 40(8): 202-210. doi: 10.12461/PKU.DXHX202409129
2. [2]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
3. [3]
  .
  南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积
  . CCS Chemistry, 2025, 7(0): -.
4. [4]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
5. [5]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
6. [6]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
7. [7]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
8. [8]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
9. [9]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
10. [10]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
11. [11]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
12. [12]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
13. [13]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
14. [14]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
15. [15]
  Xuefei Leng , Yanshai Wang , Hai Wang , Shengyang Tao . The In-Depth integration of “Industry-University-Research” in the Exploration and Practice of “Comprehensive Training in Polymer Engineering”. University Chemistry, 2025, 40(4): 66-71. doi: 10.12461/PKU.DXHX202405105
16. [16]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
17. [17]
  Ke Qiu , Fengmei Wang , Mochou Liao , Kerun Zhu , Jiawei Chen , Wei Zhang , Yongyao Xia , Xiaoli Dong , Fei Wang . A Fumed SiO₂-based Composite Hydrogel Polymer Electrolyte for Near-Neutral Zinc-Air Batteries. Acta Physico-Chimica Sinica, 2024, 40(3): 2304036-0. doi: 10.3866/PKU.WHXB202304036
18. [18]
  Minghui Wu , Markus Mühlinghaus , Xuechao Li , Chaojie Xu , Qiang Chen , Haiming Zhang , Klaus Müllen , Lifeng Chi . On-Surface Synthesis of Chevron-Shaped Conjugated Ladder Polymers Consisting of Benzo[a]azulene Units. Acta Physico-Chimica Sinica, 2024, 40(8): 2307024-0. doi: 10.3866/PKU.WHXB202307024
19. [19]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
20. [20]
  Ruoqian Zhang , Chaoqun Mu , Yali Hou , Mingming Zhang . 四苯乙烯基多组分金属有机笼的构筑及其固态发光性能研究. University Chemistry, 2025, 40(8): 277-283. doi: 10.12461/PKU.DXHX202410027

Get Citation

PDF

XML

Metrics

PDF Downloads(1225)
Abstract views(2901)
HTML views(20)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis of Poly(9,9-diallylfluorene) and the Mechanism of Its Single Green Emission

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

Metrics

通讯作者: 陈斌, bchen63@163.com