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]
  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
2. [2]
  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-. doi: 10.3866/PKU.WHXB202310013
3. [3]
  Ziheng Zhuang , Xiao Xu , Kin Shing Chan . Superdrugs for Superbugs. University Chemistry, 2024, 39(9): 128-133. doi: 10.3866/PKU.DXHX202309040
4. [4]
  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
5. [5]
  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
6. [6]
  Peng Zhan . Practice and Reflection in Training Medicinal Chemistry Graduate Students. University Chemistry, 2024, 39(6): 112-121. doi: 10.3866/PKU.DXHX202402022
7. [7]
  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
8. [8]
  Haiyu Nie , Chenhui Zhang , Fengpei Du . Ideological and Political Design for the Preparation, Characterization and Particle Size Control Experiment of Nanoemulsion. University Chemistry, 2024, 39(2): 41-46. doi: 10.3866/PKU.DXHX202306055
9. [9]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
10. [10]
  Zheqi Wang , Yawen Lin , Shunliu Deng , Huijun Zhang , Jinmei Zhou . Antiviral Strategies: A Brief Review of the Development History of Small Molecule Antiviral Drugs. University Chemistry, 2024, 39(9): 85-93. doi: 10.12461/PKU.DXHX202403108
11. [11]
  Xingyang LI , Tianju LIU , Yang GAO , Dandan ZHANG , Yong ZHOU , Meng PAN . A superior methanol-to-propylene catalyst: Construction via synergistic regulation of pore structure and acidic property of high-silica ZSM-5 zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1279-1289. doi: 10.11862/CJIC.20240026
12. [12]
  Yanhui XUE , Shaofei CHAO , Man XU , Qiong WU , Fufa WU , Sufyan Javed Muhammad . Construction of high energy density hexagonal hole MXene aqueous supercapacitor by vacancy defect control strategy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1640-1652. doi: 10.11862/CJIC.20240183
13. [13]
  Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O₂的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
14. [14]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
15. [15]
  Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
16. [16]
  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
17. [17]
  Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
18. [18]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
19. [19]
  Rui Li , Huan Liu , Yinan Jiao , Shengjian Qin , Jie Meng , Jiayu Song , Rongrong Yan , Hang Su , Hengbin Chen , Zixuan Shang , Jinjin Zhao . 卤化物钙钛矿的单双向离子迁移. Acta Physico-Chimica Sinica, 2024, 40(11): 2311011-. doi: 10.3866/PKU.WHXB202311011
20. [20]
  Doudou Qin , Junyang Ding , Chu Liang , Qian Liu , Ligang Feng , Yang Luo , Guangzhi Hu , Jun Luo , Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(503)
HTML views(53)

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