Citation: Chen Jiang, Xing Wu, Na Zhang, Fang Chen, Ru-ke Bai. Synthesis and Two-dimentional Self-assembly of Amphiphilic and Conjugated Polymers Based on Poly(phenylenebutadiynylene)s[J]. Acta Polymerica Sinica, ;2018, 0(11): 1442-1450. doi: 10.11777/j.issn1000-3304.2018.18100 shu

Synthesis and Two-dimentional Self-assembly of Amphiphilic and Conjugated Polymers Based on Poly(phenylenebutadiynylene)s

Key Laboratory of Soft Matter Chemistry, Chinese Academy of Sciences; Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026

Corresponding author: Ru-ke Bai, bairk@ustc.edu.cn
Received Date: 4 April 2018
Revised Date: 22 April 2018
Available Online: 6 September 2018

Amphiphilic and conjugated polymers based on poly(phenylenebutadiynylene)s (A-PPB) were designed and synthesized, which were consisted of a hydrophobic rigid conjugated main chain and hydrophilic flexible side chains with carboxylic anions. Structure and degree of polymerization (DP) of the polymers were examined by proton nuclear magnetic resonance (¹H-NMR), Fourier transform infrared spectroscopy (FTIR) and Raman spectroscopy. The two dimensional self-assembly of the amphiphilic conjugated polymers was investigated in different solvents and their mixtures. The morphology of the aggregates was characterized by transmission electron microscopy (TEM). The results showed that A-PPB in water self-assembled into two-dimentional supramolecular nanosheets (2D-SNS) with size ranged from hundred nanometers to several microns. The thickness of 2D-SNS was measured to be about 5 nm by atomic force microscopy (AFM), indicating a stack of 3 layers. The results of high-resolution TEM (HRTEM), selected-area electron diffraction (SAED) and X-ray diffraction (XRD) demonstrated that 2D-SNS was formed by the parallel arrangement of A-PPB, and the distance between the adjacent two A-PPB chains was consistent with the typical π-π stacking distance. On the other hand, A-PPB in methanol formed irregular aggregates because of its high solubility. However, when toluene was added into the methanolsolution of A-PPB, multilayered aggregates were obtained. Moreover, self-assembly of the non-amphiphilic precursor PPB was also examined in a mixed solvent of chloroform and methanol, and the TEM images showed that PPB formed multi-layered aggregates. This result indicated that the amphiphilicity and the electrostatic repulsion of the polymer chains played an important role in the formation of the layered sheets. In addition, DP of A-PPB is also important for 2D self-assembly of the polymers. When DP was 8, amphiphilic oligo(phenylenebutadiynylene)s formed disordered aggregates. In conclusion, this work provides significant information for 2D self-assembly of linear amphiphilic and conjugated polymers.
- Amphiphilic,
- Conjugated polymer,
- Two-dimentional self-assembly,
- Supramolecular nanosheet
1. [1]
  Cheng Y J, Yang S H, Hsu C S. Chem Rev, 2009, 109(11): 5868 − 5923
2. [2]
  Lei T, Wang J Y, Pei J. Acc Chem Res, 2014, 47(4): 1117 − 1126
3. [3]
  Yao Y, Dong H, Hu W. Adv Mater, 2016, 28(22): 4513 − 4523
4. [4]
  Savagatrup S, Printz A D, O’Connor T F, Zaretski A V, Lipomi D J. Chem Mater, 2014, 26(10): 3028 − 3041
5. [5]
  Onorato J, Pakhnyuk V, Luscombe C K. Polym J, 2017, 49(1): 41 − 60
6. [6]
  Yu Z, Lu K, Wei Z X. Sci China Chem, 2012, 55(11): 2283 − 2291
7. [7]
  Pecher J, Mecking S. Chem Rev, 2010, 110(10): 6260 − 6279
8. [8]
  Feng L, Zhu C, Yuan H, Liu L, Lv F, Wang S. Chem Soc Rev, 2013, 42(16): 6620 − 6633
9. [9]
  Yu Z, Yan H, Lu K, Zhang Y, Wei Z. RSC Adv, 2012, 2(1): 338 − 343
10. [10]
  Cativo M H M, Kim D K, Riggleman R A, Yager K G, Nonnenmann S S, Chao H, Bonnell D A, Black C T, Kagan C R, Park S J. ACS Nano, 2014, 8(12): 12755 − 12762
11. [11]
  Kamps A C, Cativo M H M, Fryd M, Park S J. Macromolecules, 2013, 47(1): 161 − 164
12. [12]
  Yang S, Shin S, Choi I, Lee J, Choi T L. J Am Chem Soc, 2017, 139(8): 3082 − 3088
13. [13]
  Huang Y, Mai Y, Yang X, Beser U, Liu J, Zhang F, Yan D, Müllen K, Feng X. J Am Chem Soc, 2015, 137(36): 11602 − 11605
14. [14]
  Huang Y, Yuan R, Xu F, Mai Y, Feng X, Yan D. Polym Chem, 2016, 7(6): 1234 − 1238
15. [15]
  Novoselov K S, Geim A K, Morozov S V, Jiang D, Zhang Y, Dubonos S V, Grigorieva I V, Firsov A A. Science, 2004, 306(5696): 666 − 669
16. [16]
  Cai S L, Zhang W G, Zuckermann R N, Li Z T, Zhao X, Liu Y. Adv Mater, 2015, 27(38): 5762 − 5770
17. [17]
  Zhang N, Wang T, Wu X, Jiang C, Zhang T, Jin B, Ji H, Bai W, Bai R. ACS Nano, 2017, 11(7): 7223 − 7229
18. [18]
  Vokatá T, Kumar M R, Park K, Moon J H, Lee S. Syn Lett, 2013, 24(12): 1563 − 1567
19. [19]
  Lo P K, Sleiman H F. Macromolecules, 2008, 41(15): 5590 − 5603
20. [20]
  Baier M C, Huber J, Mecking S. J Am Chem Soc, 2009, 131(40): 14267 − 14273
21. [21]
  Shi Y, Wu H, Xue L, Li X. J Colloid Interface Sci, 2012, 365(1): 172 − 177
22. [22]
  Tan C, Pinto M R, Schanze K S. Chem Commun, 2002, (5): 446 − 447
23. [23]
  Zhao X, Pinto M R, Hardison L M, Mwaura J, Müller J, Jiang H, Witker D, Kleiman V D, Reynolds J R, Schanze K S. Macromolecules, 2006, 39(19): 6355 − 6366
24. [24]
  Koenen J M, Zhu X, Pan Z, Feng F, Yang J, Schanze K S. ACS Macro Lett, 2014, 3(5): 405 − 409
25. [25]
  Lee K, Kim H J, Kim J. Adv Funct Mater, 2012, 22(5): 1076 − 1086
26. [26]
  Vandeleene S, Verswyvel M, Verbiest T, Koeckelberghs G. Macromolecules, 2010, 43(18): 7412 − 7423
27. [27]
  Zhang N, Wang T, Wu X, Jiang C, Chen F, Bai W, Bai R. RSC Adv, 2018, 8(7): 3803 − 3808
28. [28]
  Balakrishnan K, Datar A, Zhang W, Yang X, Naddo T, Huang J, Zuo J, Yen M, Moore J S, Zang L. J Am Chem Soc, 2006, 128(20): 6576 − 6577
29. [29]
  Li Z, Tang M, Dai J, Wang T, Wang Z, Bai W, Bai R. Macromolecules, 2017, 50(11): 4292 − 4299
30. [30]
  Maeda K, Hong L, Nishihara T, Nakanishi Y, Miyauchi Y, Kitaura R, Ousaka N, Yashima E, Ito H, Itami K. J Am Chem Soc, 2016, 138(34): 11001 − 11008
31. [31]
  Huang Wei(黄维). Scientia Sinica Chemica(中国科学: 化学), 2013, 43(2): 125 − 141
1. [1]
  .
  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): -.
2. [2]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . 优化氮化碳纳米片/球形共轭聚合物S型异质结界面电场以促进析氢反应. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-. doi: 10.1016/j.actphy.2025.100095
3. [3]
  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
4. [4]
  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
5. [5]
  Wenjian Zhang , Mengxin Fan , Wenwen Fei , Wei Bai . Cultivation of Critical Thinking Ability: Based on RAFT Polymerization-Induced Self-Assembly. University Chemistry, 2025, 40(4): 108-112. doi: 10.12461/PKU.DXHX202406099
6. [6]
  Huanhuan XIE , Yingnan SONG , Lei LI . Two-dimensional single-layer BiOI nanosheets: Lattice thermal conductivity and phonon transport mechanism. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 702-708. doi: 10.11862/CJIC.20240281
7. [7]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
8. [8]
  Shiyang He , Dandan Chu , Zhixin Pang , Yuhang Du , Jiayi Wang , Yuhong Chen , Yumeng Su , Jianhua Qin , Xiangrong Pan , Zhan Zhou , Jingguo Li , Lufang Ma , Chaoliang Tan . 铂单原子功能化的二维Al-TCPP金属-有机框架纳米片用于增强光动力抗菌治疗. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-. doi: 10.1016/j.actphy.2025.100046
9. [9]
  Mengfei He , Chao Chen , Yue Tang , Si Meng , Zunfa Wang , Liyu Wang , Jiabao Xing , Xinyu Zhang , Jiahui Huang , Jiangbo Lu , Hongmei Jing , Xiangyu Liu , Hua Xu . Epitaxial Growth of Nonlayered 2D MnTe Nanosheets with Thickness-Tunable Conduction for p-Type Field Effect Transistor and Superior Contact Electrode. Acta Physico-Chimica Sinica, 2025, 41(2): 100016-. doi: 10.3866/PKU.WHXB202310029
10. [10]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
11. [11]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
12. [12]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
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]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
15. [15]
  .
  CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
  . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  Rui Li , Jiayu Zhang , Anyang Li . Two Levels of Understanding of Chemical Bonds: a Case of the Bonding Model of Hypervalent Molecules. University Chemistry, 2024, 39(2): 392-398. doi: 10.3866/PKU.DXHX202308051
20. [20]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(109)
HTML views(6)

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 and Two-dimentional Self-assembly of Amphiphilic and Conjugated Polymers Based on Poly(phenylenebutadiynylene)s

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