Citation: Zhang Yu-Jian, Xie Bin, Jiang Tao. Preparation and Properties of Crown Ethers Containing Amphiphilic Copolymer Nano-aggregates[J]. Acta Chimica Sinica, ;2016, 74(9): 752-757. doi: 10.6023/A16060281 shu

Preparation and Properties of Crown Ethers Containing Amphiphilic Copolymer Nano-aggregates

Zhang Yu-Jian ^a,b ,
Xie Bin ^b ,
Jiang Tao ^a,*,,

a.
Tianjin University of Science and Technology, Materials Science and Chemical Engineering Institute, Tianjin 300457, China
b.
Petrochemical Research Institute of PetroChina, Synthetic Resins and Processing Applications Lab, Beijing 100195, China

Corresponding author: Jiang Tao, jiangtao@tust.edu.cn
Received Date: 7 June 2016

Fund Project: Application Foundation and Frontier Technology Research Program of Tianjin Municipality 16JCZDJC31600

Figures(12)

In this paper, an amphiphilic copolymer poly(2, 2'-(1, 10-diaza-[18]crown-6-1, 10-diyl)diethyl 5-((adenin-9-yl)-methyl)isophthalate) (PDCAI) was designed and synthesized by simulating the chemical structure of DNA. We observed its self-organized morphology in the aqueous solution and in potassium solution with scanning electron microscopy (SEM), amphiphilic copolymer PDCAI spontaneously aggregated into strip aggregates in aqueous solution, and which could change into a rod, nanotube or helical rod aggregates in KNO₃ solution. In addition, the molecular recognition between copolymer PDCAI and thymine substrate has been studied via FT-IR, and it is found that C₂=O of thymine had recognized with PDCAI through complementary nucleobases in aqueous solution, the C₂=O stretching band of thymine at 1737 cm^-1shifted to 1710 cm^-1 after recognition, however, the band of the C₄=O of thymine did not change at 1677 cm^-1. Meanwhile we attempted to regulate the molecular recognition of copolymer PDCAI with thymine substrate with K⁺, we surprisingly found that hydrogen bonding occurs on C₄=O of thymine when it recognized with PDCAI in KNO₃ solution, the C₄=O stretching band of thymine at 1677 cm^-1 shifted to 1671 cm^-1, however, the band of the C₂=O of thymine did not change at 1737 cm^-1 after recognition. It proves that the recognizing conformation of thymine re-organized during identification process due to the transition of aggregation form of PDCAI. And we further confirmed and studied the hydrogen bond formation and fracture process by variable temperature FT-IR, which formed at room temperature gradually broke while temperature rising from 25℃ up to 115℃, when temperature was above 115℃, hydrogen bonds broke completely, thymine and PDCAI return to their pre-recognition state. The formations of hydrogen bonds between adenine in the polymer and thymine substrate in nanospheres could enhance their interaction and loading capacity. The results have reference value for research of molecular characteristics of polymer which spontaneously formed spiral, preparation of helical polymer, and nucleic acid imitation drug carriers and its function regulation.
- drug carriers,
- aggregates,
- hydrogen bond,
- ion regulation
1. [1]
  Ben-Naim, A. Hydrophobic Interactions, Plenum Press, New York, 1980, p. 311.
2. [2]
  Saenger, W. Principles of Nucleic Acid Structure, Springer, New York, 1984, p. 298.
3. [3]
  Gao, Y. X.; Hu, J.; Ju, Y. Acta Chim. Sinica 2016, 74(4), 312. doi: 10.6023/A16010016
4. [4]
  Liu, C.; Yu, G.; Huang, C. Y.; Wang, C. S. Acta Chim. Sinica 2015, 73(4), 357. doi: 10.6023/A14120869
5. [5]
  Hawker, C. J.; Wooley, K. L. Science 2005, 309, 1200. doi: 10.1126/science.1109778
6. [6]
  Berti, D.; Luisi, P. L.; Baglioni, P. Colloids & Surfaces 2000, 167, 95.
7. [7]
  Eschenmoser, A. Science 1999, 284, 2118. doi: 10.1126/science.284.5423.2118
8. [8]
  Zhang, L.; Peritz, A.; Meggers, E. J. Am. Chem. Soc. 2005, 127, 4174. doi: 10.1021/ja042564z
9. [9]
  Yoshimoto, K.; Nishizawa, S.; Minagawa, M. J. Am. Chem. Soc. 2003, 125, 8982. doi: 10.1021/ja029786m
10. [10]
  Nowick, J. S.; Cao, T.; Noronha, G. J. Am. Chem. Soc. 1994, 116, 3285. doi: 10.1021/ja00087a014
11. [11]
  Baglioni, P.; Berti, D. Colloid Interface Sci. 2003, 8, 55. doi: 10.1016/S1359-0294(03)00015-3
12. [12]
  Miao, W.; Du, X.; Liang, Y. Langmuir 2003, 19, 5389. doi: 10.1021/la0345690
13. [13]
  Yashima, E.; Maeda, K. Chem.-Eur. J. 2004, 10, 42. doi: 10.1002/(ISSN)1521-3765
14. [14]
  Yang, M. J. Beijing Med. Univ. 1998, 30(2), 97.
15. [15]
  Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017. doi: 10.1021/ja01002a035
16. [16]
  Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009. doi: 10.1002/(ISSN)1521-3773
17. [17]
  Huang, F. H.; Ji, X. F.; Yao, Y. J. Am. Chem. Soc. 2013, 135, 74. doi: 10.1021/ja3108559
18. [18]
  Ji, X.; Dong, S.; Wei, P.; Xia, D.; Huang, F. Adv. Mater. 2013, 25, 5725. doi: 10.1002/adma.v25.40
19. [19]
  Masuda, M.; Okada, Y. Macromolecules 2000, 33, 9233. doi: 10.1021/ma001157e
20. [20]
  Buchet, R.; Sandorfy, C. J. Phys. Chem. 1983, 87, 275. doi: 10.1021/j100225a021
21. [21]
  Alabugin, I. V.; Manoharan, M.; Peabody, S.; Weinhold, F. J. Am. Chem. Soc. 2003, 125, 5973. doi: 10.1021/ja034656e
22. [22]
  Florian, J. Spectrochim. Acta 1993, 49A, 921.
23. [23]
  Zhang, Y. J.; Xie, B. Acta Chim. Sinica 2012, 70, 499. doi: 10.6023/A1110271
1. [1]
  Jiashuang Lu , Xiaoyang Xu , Youqing He , Mingyue Wu , Ruixin Shi , Wenfang Yu , Hang Lu , Ji Liu , Qingzeng Zhu . 生命健康中的有机硅高分子. University Chemistry, 2025, 40(8): 169-180. doi: 10.12461/PKU.DXHX202409143
2. [2]
  Huiying Xu , Minghui Liang , Zhi Zhou , Hui Gao , Wei Yi . Application of Quantum Chemistry Computation and Visual Analysis in Teaching of Weak Interactions. University Chemistry, 2025, 40(3): 199-205. doi: 10.12461/PKU.DXHX202407011
3. [3]
  Xue Wu , Yupeng Liu , Bingzhe Wang , Lingyun Li , Zhenjian Li , Qingcheng Wang , Quansheng Cheng , Guichuan Xing , Songnan Qu . Rationally assembling different surface functionalized carbon dots for enhanced near-infrared tumor photothermal therapy. Acta Physico-Chimica Sinica, 2025, 41(9): 100109-0. doi: 10.1016/j.actphy.2025.100109
4. [4]
  Yinglian LI , Chengcheng ZHANG , Xinyu ZHANG , Xinyi WANG . Spin crossover in [Co(pytpy)₂]²⁺ complexes modified by organosulfonate anions. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1162-1172. doi: 10.11862/CJIC.20240087
5. [5]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
6. [6]
  Xiaoxuan Yu , Wukun Liu . Practice of Ideological and Political Education in Medicinal Chemistry for Pharmacy Administration Major: A Case Study on the Discovery of Cisplatin’s Anticancer Function. University Chemistry, 2025, 40(4): 408-414. doi: 10.12461/PKU.DXHX202405200
7. [7]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
8. [8]
  Xiuya Ma , Yu Chen , Yan Zhang . Stories about Pharmaceuticals. University Chemistry, 2025, 40(7): 232-240. doi: 10.12461/PKU.DXHX202408003
9. [9]
  Jiaxuan Zuo , Kun Zhang , Jing Wang , Xifei Li . Nucleation Regulation and Mechanism of Precursors for Nickel Cobalt Manganese-based Cathode Materials in Lithium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(1): 100009-0. doi: 10.3866/PKU.WHXB202404042
10. [10]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
11. [11]
  Ziheng Zhuang , Xiao Xu , Kin Shing Chan . Superdrugs for Superbugs. University Chemistry, 2024, 39(9): 128-133. doi: 10.3866/PKU.DXHX202309040
12. [12]
  Xiting Zhou , Zhipeng Han , Xinlei Zhang , Shixuan Zhu , Cheng Che , Liang Xu , Zhenyu Sun , Leiduan Hao , Zhiyu Yang . Dual Modulation via Ag-Doped CuO Catalyst and Iodide-Containing Electrolyte for Enhanced Electrocatalytic CO₂ Reduction to Multi-Carbon Products: A Comprehensive Chemistry Experiment. University Chemistry, 2025, 40(7): 336-344. doi: 10.12461/PKU.DXHX202412070
13. [13]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-0. doi: 10.3866/PKU.WHXB202310013
14. [14]
  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
15. [15]
  Ruiqing LIU , Wenxiu LIU , Kun XIE , Yiran LIU , Hui CHENG , Xiaoyu WANG , Chenxu TIAN , Xiujing LIN , Xiaomiao FENG . Three-dimensional porous titanium nitride as a highly efficient sulfur host. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 867-876. doi: 10.11862/CJIC.20230441
16. [16]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
17. [17]
  Peng Zhan . Practice and Reflection in Training Medicinal Chemistry Graduate Students. University Chemistry, 2024, 39(6): 112-121. doi: 10.3866/PKU.DXHX202402022
18. [18]
  Zhibei Qu , Changxin Wang , Lei Li , Jiaze Li , Jun Zhang . Organoid-on-a-Chip for Drug Screening and the Inherent Biochemistry Principles. University Chemistry, 2024, 39(7): 278-286. doi: 10.3866/PKU.DXHX202311039
19. [19]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
20. [20]
  Xinghai Liu , Hongke Wu . Exploration and Practice of Ideological and Political Education in Heterocyclic Chemistry Based on "Fentanyl" Event. University Chemistry, 2024, 39(8): 359-364. doi: 10.3866/PKU.DXHX202312100

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(678)
HTML views(59)

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