Citation: Ai-hui Liang, Han Wang, Tian Cao, Ming Luo, De-wang Liu, Yi Chen, Zhi-ping Wang. Synthesis and Properties of Phosphorescent Polymers with Aggregation-induced Emission[J]. Acta Polymerica Sinica, ;2019, 50(1): 27-35. doi: 10.11777/j.issn1000-3304.2018.18160 shu

Synthesis and Properties of Phosphorescent Polymers with Aggregation-induced Emission

Key Laboratory of Functional Small Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Ai-hui Liang, lah14god@163.com
Received Date: 10 July 2018
Revised Date: 25 July 2018
Available Online: 21 September 2018

A series of phosphorescent polymers with aggregation-induced emission (AIE) feature were synthesized by palladium-catalyzed Suzuki polycondensation of tetraphenylethene (TPE), iridium complex and 9,9-dioctylfluorene. All the obtained polymers are soluble in common organic solvents, such as chloroform, dichloromethane and tetrahydrofuran (THF), at room temperature, but insoluble in water. Their thermal and photophysical properties, as well as AIE performance of the resulting phosphorescent polymers are investigated with different feed ratios of iridium complex varing from 0.5% to 4%. These polymers display good thermal properties with a high thermal degradation temperature (> 300 °C) and glass transition temperature (≈ 100 °C). Polymer PFTPE displays the maximum photoluminescent (PL) emission at 440 nm. Relative to PFTPE, all the phosphorescent polymers prepared with iridium complex feed ratios in the range of 0.5% − 4% emit green light with an emission peak at about 505 nm. AIE performances of these phosphorescent polymers are examined by studying the PL emission behaviour of their diluted mixture in THF/water under different water fractions (f_w). The aggregates are prepared by adding different fractions (f_w = 0% to 90%) of ultra-pure water into THF solution. Both PL intensity and quantum yield (Ф_PL) of PFTPE-Fir0.5 and PFTPE-Fir1 exhibit an upward trend with the increasing f_w from 0% to 80%. However, when f_w further increases from 80% to 90%, PL intensity and Ф_PL show downward trend. The maximum values of Ф_PL are 37.3% for PFTPE-FIr0.5 and 38.6% for PFTPE-FIr1, respectively. Similarly, PL intensity and Ф_PL of PFTPE-FIr2 and PFTPE-FIr4 display the same behaviour as PFTPE-FIr0.5 and PFTPE-FIr1. And PFTPE-FIr2 and PFTPE-FIr4 reach the maximum Ф_PL value of 37.2% and 39.9%, respectively, at f_w of 30%. This indicates that these phosphorescent polymers have AIE feature, suggesting that they are potential materials for fabrication of organic light-emitting diodes and fluorescent sensors.
- Aggregation-induced emission,
- Iridium complex,
- Phosphorescent polymer,
- Tetraphenylethene
1. [1]
  Tang C W, VanSlyke S A. Appl Phys Lett, 1987, 51(12): 913 − 915 doi: 10.1063/1.98799
2. [2]
  Wong W Y, Ho C L. Coord Chem Rev, 2009, 253(13-14): 1709 − 1758 doi: 10.1016/j.ccr.2009.01.013
3. [3]
  Wang K, Zhao F, Wang C, Chen S, Chen D, Zhang H, Liu Y, Ma D, Wang Y. Adv Funct Mater, 2013, 23(21): 2672 − 2680 doi: 10.1002/adfm.v23.21
4. [4]
  Zhong C, Duan C, Huang F, Wu H, Cao Y. Chem Mater, 2010, 23(3): 326 − 340
5. [5]
  Zheng H, Zheng Y, Liu N, Ai N, Wang Q, Wu S, Zhou J, Hu D, Yu S, Han S, Xu W, Luo C, Meng Y, Jiang Z, Chen Y, Li D, Huang F, Wang J, Peng J, Cao Y. Nat Commun, 2013, 4: 1971 doi: 10.1038/ncomms2971
6. [6]
7. [7]
  Ma Y G, Zhang H Y, Shen J C, Che C M. Synth Met, 1998, 94(3): 245 − 248 doi: 10.1016/S0379-6779(97)04166-0
8. [8]
  Baldo M A, O'Brien D F, You Y, Shoustikov A, Sibley S, Thompson M E, Forrest S R. Nature, 1998, 395(6698): 151 − 154 doi: 10.1038/25954
9. [9]
  Yang X, Zhou G, Wong W Y. Chem Soc Rev, 2015, 44(23): 8484 − 8575 doi: 10.1039/C5CS00424A
10. [10]
  Ulbricht C, Beyer B, Friebe C, Winter A, Schubert U S. Adv Mater, 2009, 21(44): 4418 − 4441 doi: 10.1002/adma.v21:44
11. [11]
  Wong W Y, Ho C L. J Mater Chem, 2009, 19(26): 4457 − 4482 doi: 10.1039/b819943d
12. [12]
  Jiang B, Gu Y, Qin J, Ning X, Gong S, Xie G, Yang C. J Mater Chem C, 2016, 4(16): 3492 − 3498 doi: 10.1039/C6TC00148C
13. [13]
  Liang A, Ying L, Huang F. J Inorg Organomet Polym Mater, 2014, 24(6): 905 − 926 doi: 10.1007/s10904-014-0099-8
14. [14]
  Zhang K, Zhong C, Liu S, Liang A H, Dong S, Huang F. J Mater Chem C, 2014, 2(17): 3270 − 3277 doi: 10.1039/C3TC32022G
15. [15]
  Tang C, Liu X D, Liu F, Wang X L, Xu H, Huang W. Macromol Chem Phys, 2013, 214(3): 314 − 342 doi: 10.1002/macp.201200305
16. [16]
  Zhu M, Li Y, Cao X, Jiang B, Wu H, Qin J, Cao Y, Yang C. Macromol Rapid Commun, 2014, 35(24): 2071 − 2076 doi: 10.1002/marc.v35.24
17. [17]
  Yang X, Zhou G, Wong W Y. J Mater Chem C, 2014, 2(10): 1760 − 1778 doi: 10.1039/c3tc31953a
18. [18]
  Shao S, Ding J, Wang L, Jing X, Wang F. J Am Chem Soc, 2012, 134(50): 20290 − 20293 doi: 10.1021/ja310158j
19. [19]
  Hong Y, Lam J W Y, Tang B Z. Chem Soc Rev, 2011, 40(11): 5361 − 5388 doi: 10.1039/c1cs15113d
20. [20]
  Liang A, Wang H, Chen Y, Zheng X, Cao T, Yang X, Cai P, Wang Z, Zhang X, Huang F. Dyes Pigm, 2018, 149: 399 − 406 doi: 10.1016/j.dyepig.2017.10.020
21. [21]
  Tang B Z, Zhan X, Yu G, Sze Lee P P, Liu Y, Zhu D. J Mater Chem, 2001, 11(12): 2974 − 2978 doi: 10.1039/b102221k
22. [22]
23. [23]
24. [24]
  Liu Z, Hu S, Zhang L, Chen J, Peng J, Cao Y. Sci China Chem, 2013, 56(8): 1129 − 1136 doi: 10.1007/s11426-013-4875-z
25. [25]
  Liu J, Lam J W Y, Tang B Z. Chem Rev, 2009, 109(11): 5799 − 5867 doi: 10.1021/cr900149d
26. [26]
27. [27]
  He B, Ye S, Guo Y, Chen B, Xu X, Qiu H, Zhao Z. Sci China Chem, 2013, 56(9): 1221 − 1227 doi: 10.1007/s11426-013-4929-2
28. [28]
  Chen M, Nie H, Song B, Li L, Sun J Z, Qin A, Tang B Z. J Mater Chem C, 2016, 4(14): 2901 − 2908 doi: 10.1039/C5TC03299G
29. [29]
  Luo Y, Aziz H. Adv Funct Mater, 2010, 20(8): 1285 − 1293 doi: 10.1002/adfm.v20:8
1. [1]
  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
2. [2]
  Pan Li , Huguo Shen , Cong Hua , Jinjie Fang , Xiangying Chi , Quan Jiang , Zichen Feng , Ye Kang , Bin Zheng . Synthesis and Characterization of an Aggregation-Induced Emission-Active Organic Cage Molecule: A Proposed Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(11): 337-345. doi: 10.12461/PKU.DXHX202502083
3. [3]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
4. [4]
  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
5. [5]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
6. [6]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
7. [7]
  Hongxia Yan , Weixu Feng , Junyan Yao , Wei Tian , Rui Wang . Illuminating the Teaching of Science and Engineering Graduate Courses with “Curriculum Ideology and Politics”. University Chemistry, 2024, 39(6): 122-127. doi: 10.3866/PKU.DXHX202310059
8. [8]
  Chunyuan Kang , Xiaoyu Li , Fan Yang , Bai Yang . Ionic-bond crosslinked carbonized polymer dots for tunable and enhanced room temperature phosphorescence. Acta Physico-Chimica Sinica, 2026, 42(1): 100156-0. doi: 10.1016/j.actphy.2025.100156
9. [9]
  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
10. [10]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
11. [11]
  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
12. [12]
  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
13. [13]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
14. [14]
  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
15. [15]
  Huihua GONG , Tianhua CUI , Li JI , Jichuan ZHANG , Liyuan ZHANG , Yan CHEN , Zhenye WANG , Jiaqi XU , Ruixiang LI . Hydrogenation of CO₂ to formate catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated iridium(Ⅰ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2609-2620. doi: 10.11862/CJIC.20250170
16. [16]
  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
17. [17]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(239)
HTML views(19)

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