Citation: Zhang Yi, Liu Yu. Supramolecular Assemblies of Multi-Charged Cyclodextrins[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3802-3811. doi: 10.6023/cjoc202004040 shu

Supramolecular Assemblies of Multi-Charged Cyclodextrins

Zhang Yi ,
Liu Yu ^,

State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Liu Yu, yuliu@nankai.edu.cn
Received Date: 25 April 2020
Revised Date: 29 April 2020
Available Online: 11 May 2020
Fund Project: the National Natural Science Foundation of China 21861132001Project supported by the National Natural Science Foundation of China (Nos. 21772099, 21861132001)the National Natural Science Foundation of China 21772099

Figures(13)

As a class of macrocyclic host with excellent water solubility, low biotoxicity and high charge density, multi-charged cyclodextrins have been extensively studied because they can interact with organic/inorganic/biological molecules through multiple synergistic forces such as the hydrophobic cavities and electrostatic interactions to construct the smart supramolecular assemblies with stable topology, functional diversity and stimulus responsiveness. The latest research progress of pH-, photo-, enzyme-, redox-, magnetic-and multi-stimulus responsive smart supramolecular assemblies, which are constructed by typical positively/negatively charged and amphiphilic multi-charged cyclodextrins including their application in the fields of drug delivery, controlled release and sensory detection is introduced, and the challenges and future developments of multi-charged cyclodextrin smart supramolecular assemblies are discussed.
- multi-charged cyclodextrin,
- supramolecular assembly,
- stimulus responsiveness,
- smart material
1. [1]
2. [2]
  Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081. doi: 10.1021/ja00093a004
3. [3]
4. [4]
  (a) Eliseev, A. V.; Schneider, H.-J. Angew. Chem., Int. Ed. 1993, 32, 1331.
  (b) Steffen, A.; Thiele, C.; Tietze, S.; Strassnig, C.; Kämper, A.; Lengauer, T.; Wenz, G.; Apostolakis, J. Chem.-Eur. J. 2007, 13, 6801.
5. [5]
  (a) Zhang, Y. M.; Liu, Y. H.; Liu, Y. Adv. Mater. 2020, 32, e1806158.
  (b) Liao, R.; Lv, P.; Wang, Q.; Zheng, J.; Feng, B.; Yang, B. Biomater. Sci. 2017, 5, 1736.
  (c) Yao, X.; Mu, J.; Zeng, L.; Lin, J.; Nie, Z.; Jiang, X.; Huang, P. Mater. Horiz. 2019, 6, 846.
6. [6]
  (a) Bom, A.; Bradley, M.; Cameron, K.; Clark, J. K.; Van Egmond, J.; Feilden, H.; Maclean, E. J.; Muir, A. W.; Palin, R.; Rees, D. C.; Zhang, M.-Q. Angew. Chem., Int. Ed. 2002, 41, 265.
  (b) Adam, J. M.; Bennett, D. J.; Bom, A.; Clark, J. K.; Feilden, H.; Hutchinson, E. J.; Palin, R.; Prosser, A.; Rees, D. C.; Rosair, G. M.; Stevenson, D.; Tarver, G. J.; Zhang, M.-Q. J. Med. Chem. 2002, 45, 1806.
7. [7]
  Jones, S. T.; Cagno, V.; Janeček, M.; Ortiz, D.; Gasilova, N.; Piret, J.; Gasbarri, M.; Constant, D. A.; Han, Y.; Vuković, L.; Král, P.; Kaiser, L.; Huang, S.; Constant, S.; Kirkegaard, K.; Boivin, G.; Stellacci, F.; Tapparel, C. Sci. Adv. 2020, 6, eaax9318. doi: 10.1126/sciadv.aax9318
8. [8]
  Sun, H.-L.; Zhang, Y.-M.; Chen, Y.; Liu, Y. Sci. Rep. 2016, 6, 27. doi: 10.1038/s41598-016-0026-z
9. [9]
  Li, J. J.; Chen, Y.; Yu, J.; Cheng, N.; Liu, Y. Adv. Mater. 2017, 29, 1701905. doi: 10.1002/adma.201701905
10. [10]
  (a) Shi, R.-J.; Chen, Y.; Hou, X.-F.; Liu, Y. RSC Adv. 2016, 6, 15175.
  (b) Zhao, D.; Chen, Y.; Liu, Y. Chin. Chem. Lett. 2015, 26, 829.
11. [11]
  Díaz-Moscoso, A.; Balbuena, P.; Gómez-García, M.; Ortiz Mellet, C.; Benito, J. M.; Le Gourriérec, L.; Di Giorgio, C.; Vierling, P.; Mazzaglia, A.; Micali, N.; Defaye, J.; García Fernández, J. M. Chem. Commun. 2008, 2001.
12. [12]
  Zhao, F.; Yin, H.; Zhang, Z.; Li, J. Biomacromolecules 2013, 14, 476. doi: 10.1021/bm301718f
13. [13]
  Wang, J.; Chen, Y.; Cheng, N.; Feng, L.; Gu, B.-H.; Liu, Y. ACS Appl. Bio Mater. 2019, 2, 5898. doi: 10.1021/acsabm.9b00845
14. [14]
  (a) Lu, Y.; De Vries, W. C.; Overeem, N. J.; Duan, X.; Zhang, H.; Zhang, H.; Pang, W.; Ravoo, B. J.; Huskens, J. Angew. Chem., Int. Ed. 2019, 58, 159.
  (b) Schibilla, F.; Holthenrich, A.; Song, B.; Linard Matos, A. L.; Grill, D.; Rota Martir, D.; Gerke, V.; Zysman-Colman, E.; Ravoo, B. J. Chem. Sci. 2018, 9, 7822.
  (c) Himmelein, S.; Lewe, V.; Stuart, M. C. A.; Ravoo, B. J. Chem. Sci. 2014, 5, 1054.
15. [15]
  Ravoo, B. J.; Darcy, R. Angew. Chem., Int. Ed. 2000, 39, 4324. doi: 10.1002/1521-3773(20001201)39:23<4324::AID-ANIE4324>3.0.CO;2-O
16. [16]
  (a) Mohan Nalluri, S. K.; Bultema, J. B.; Boekema, E. J.; Ravoo, B. J. Chem. Sci. 2011, 2, 2383.
  (b) Samanta, A.; Ravoo, B. J. Chem.-Eur. J. 2014, 20, 4966.
  (c) Samanta, A.; Stuart, M. C. A.; Ravoo, B. J. J. Am. Chem. Soc. 2012, 134, 19909.
  (d) Nalluri, S. K. M.; Bultema, J. B.; Boekema, E. J.; Ravoo, B. J. Chem.-Eur. J. 2011, 17, 10297.
  (e) Moratz, J.; Stricker, L.; Engel, S.; Ravoo, B. J. Macromol. Rapid Commun. 2018, 39, 1700256.
17. [17]
  Sukegawa, T.; Furuike, T.; Niikura, K.; Yamagishi, A.; Monde, K.; Nishimura, S.-I. Chem. Commun. 2002, 430.
18. [18]
  Donohue, R.; Mazzaglia, A.; Ravoo, B. J.; Darcy, R. Chem. Commun. 2002, 2864.
19. [19]
  (a) O'mahony, A. M.; Doyle, D.; Darcy, R.; Cryan, J. F.; O'driscoll, C. M. Eur. J. Pharm. Sci. 2012, 47, 896.
  (b) Méndez-Ardoy, A.; Guilloteau, N.; Di Giorgio, C.; Vierling, P.; Santoyo-González, F.; Ortiz Mellet, C.; García Fernández, J. M. J. Org. Chem. 2011, 76, 5882.
20. [20]
  Li, P. Y.; Chen, Y.; Chen, C. H.; Liu, Y. Chem. Commun. 2019, 55, 11790. doi: 10.1039/C9CC06545H
21. [21]
  (a) Zan, M.; Li, J.; Luo, S.; Ge, Z. Chem. Commun. 2014, 50, 7824.
  (b) Zhao, D.; Yi, X.; Xu, J.; Yuan, G.; Zhuo, R.; Li, F. J. Mater. Chem. B 2017, 5, 2823.
  (c) Durmaz, Y. Y.; Lin, Y.-L.; Elsayed, M. E. H. Adv. Funct. Mater. 2013, 23, 3885.
22. [22]
  Cheng, J. G.; Yu, H. J.; Chen, Y.; Liu, Y. Bioorg. Med. Chem. 2018, 26, 2287. doi: 10.1016/j.bmc.2018.03.013
23. [23]
  Cheng, J.-G.; Zhang, Y.-M.; Liu, Y. ChemNanoMat 2018, 4, 758. doi: 10.1002/cnma.201800098
24. [24]
  Tardy, B. L.; Tan, S.; Dam, H. H.; Ejima, H.; Blencowe, A.; Qiao, G. G.; Caruso, F. Nanoscale 2016, 8, 15589. doi: 10.1039/C6NR04841B
25. [25]
  Liang, L.; Chen, Y.; Chen, X.-M.; Zhang, Y.; Liu, Y. Chin. Chem. Lett. 2018, 29, 989. doi: 10.1016/j.cclet.2017.12.022
26. [26]
  Chen, X. M.; Chen, Y.; Hou, X. F.; Wu, X.; Gu, B. H.; Liu, Y. ACS Appl. Mater. Interfaces 2018, 10, 24987. doi: 10.1021/acsami.8b08651
27. [27]
  (a) Gayam, S. R.; Venkatesan, P.; Sung, Y.-M.; Sung, S.-Y.; Hu, S.-H.; Hsu, H.-Y.; Wu, S.-P. Nanoscale 2016, 8, 12307.
  (b) Lee, J.; Oh, E.-T.; Yoon, H.; Woo Kim, C.; Han, Y.; Song, J.; Jang, H.; Joo Park, H.; Kim, C. Nanoscale 2017, 9, 6901.
  (c) Cheng, Y.-J.; Luo, G.-F.; Zhu, J.-Y.; Xu, X.-D.; Zeng, X.; Cheng, D.-B.; Li, Y.-M.; Wu, Y.; Zhang, X.-Z.; Zhuo, R.-X.; He, F. ACS Appl. Mater. Interfaces 2015, 7, 9078.
28. [28]
  Hu, P.; Chen, Y.; Li, J. J.; Liu, Y. Chem.-Asian J. 2016, 11, 505. doi: 10.1002/asia.201501029
29. [29]
  Hou, X.-F.; Chen, Y.; Liu, Y. Soft Matter 2015, 11, 2488. doi: 10.1039/C4SM02896A
30. [30]
  Han, X.; Chen, Y.; Sun, H.-L.; Liu, Y. Asian J. Org. Chem. 2018, 7, 870. doi: 10.1002/ajoc.201800076
31. [31]
  Guan, X.; Chen, Y.; Wu, X.; Li, P.; Liu, Y. Chem. Commun. 2019, 55, 953. doi: 10.1039/C8CC09047E
32. [32]
  (a) Zhao, Q.; Lian, Z.; Gao, X.; Yan, Y.; Huang, J. Langmuir 2016, 32, 11973.
  (b) Mandl, G. A.; Rojas-Gutierrez, P. A.; Capobianco, J. A. Chem. Commun. 2018, 54, 5847.
  (c) Stricker, L.; Fritz, E.-C.; Peterlechner, M.; Doltsinis, N. L.; Ravoo, B. J. J. Am. Chem. Soc. 2016, 138, 4547.
33. [33]
  Zhao, X.; Chen, Y.; Guan, X. R.; Li, P. Y.; Zhou, W. L.; Liu, Y. ChemistrySelect 2019, 4, 13241. doi: 10.1002/slct.201903889
34. [34]
  Li, Z.-Y.; Chen, Y.; Wu, H.; Liu, Y. ChemistrySelect 2018, 3, 3203. doi: 10.1002/slct.201703091
35. [35]
  Liu, Z.; Qiao, J.; Tian, Y.; Wu, M.; Niu, Z.; Huang, Y. Langmuir 2014, 30, 8938. doi: 10.1021/la501936a
36. [36]
  Liu, J.; Xu, L.; Jin, Y.; Qi, C.; Li, Q.; Zhang, Y.; Jiang, X.; Wang, G.; Wang, Z.; Wang, L. ACS Appl. Mater. Interfaces 2016, 8, 14200. doi: 10.1021/acsami.6b04462
37. [37]
  Chen, X.; Qiu, Y. K.; Owh, C.; Loh, X. J.; Wu, Y. L. Nanoscale 2016, 8, 18876. doi: 10.1039/C6NR08055C
38. [38]
  Wen, Y.; Zhang, Z.; Li, J. Adv. Funct. Mater. 2014, 24, 3874. doi: 10.1002/adfm.201303687
39. [39]
  (a) Yang, C.; Wang, X.; Li, H.; Goh, S. H.; Li, J. Biomacromolecules 2007, 8, 3365.
  (b) Yamashita, A.; Kanda, D.; Katoono, R.; Yui, N.; Ooya, T.; Maruyama, A.; Akita, H.; Kogure, K.; Harashima, H. J. Control. Release 2008, 131, 137.
40. [40]
  Ooya, T.; Choi, H. S.; Yamashita, A.; Yui, N.; Sugaya, Y.; Kano, A.; Maruyama, A.; Akita, H.; Ito, R.; Kogure, K.; Harashima, H. J. Am. Chem. Soc. 2006, 128, 3852. doi: 10.1021/ja055868+
41. [41]
  Tamura, A.; Yui, N. Biomaterials 2013, 34, 2480. doi: 10.1016/j.biomaterials.2012.12.006
42. [42]
  Schroeder, T. B. H.; Houghtaling, J.; Wilts, B. D.; Mayer, M. Adv. Mater. 2018, 30, 1705322. doi: 10.1002/adma.201705322
43. [43]
  (a) Badruddoza, A. Z. M.; Bhattarai, B.; Suri, R. P. S. ACS Sustainable Chem. Eng. 2017, 5, 9223.
  (b) Lu, A.-H.; Salabas, E. L.; Schüth, F. Angew. Chem., Int. Ed. 2007, 46, 1222.
44. [44]
  Samanta, A.; Ravoo, B. J. Angew. Chem., Int. Ed. 2014, 53, 12946. doi: 10.1002/anie.201405849
45. [45]
  Awasthi, A. A.; Singh, P. K. J. Phys. Chem. B 2017, 121, 6208. doi: 10.1021/acs.jpcb.7b03592
46. [46]
  Singh, G.; Singh, P. K. Langmuir 2019, 35, 14628. doi: 10.1021/acs.langmuir.9b03083
47. [47]
  Hu, P.; Chen, Y.; Liu, Y. Chem. Commun. 2015, 51, 10839. doi: 10.1039/C5CC03248B
1. [1]
  Xiyuan Su , Zhenlin Hu , Ye Fan , Xianyuan Liu , Xianyong Lu . Change as You Want: Multi-Responsive Superhydrophobic Intelligent Actuation Material. University Chemistry, 2024, 39(5): 228-237. doi: 10.3866/PKU.DXHX202311059
2. [2]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
3. [3]
  .
  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): -.
4. [4]
  Kai Yang , Gehua Bi , Yong Zhang , Delin Jin , Ziwei Xu , Qian Wang , Lingbao Xing . Comprehensive Polymer Chemistry Experiment Design: Preparation and Characterization of Rigid Polyurethane Foam Materials. University Chemistry, 2024, 39(4): 206-212. doi: 10.3866/PKU.DXHX202308045
5. [5]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
6. [6]
  Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
7. [7]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
8. [8]
  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
9. [9]
  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
10. [10]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
11. [11]
  Yuena Yang , Xufang Hu , Yushan Liu , Yaya Kuang , Jian Ling , Qiue Cao , Chuanhua Zhou . The Realm of Smart Hydrogels. University Chemistry, 2024, 39(5): 172-183. doi: 10.3866/PKU.DXHX202310125
12. [12]
  Hongyun Liu , Jiarun Li , Xinyi Li , Zhe Liu , Jiaxuan Li , Cong Xiao . Course Ideological and Political Design of a Comprehensive Chemistry Experiment: Constructing a Visual Molecular Logic System Based on Intelligent Hydrogel Film Electrodes. University Chemistry, 2024, 39(2): 227-233. doi: 10.3866/PKU.DXHX202309070
13. [13]
  Xingyuan Lu , Yutao Yao , Junjing Gu , Peifeng Su . Energy Decomposition Analysis and Its Application in the Many-Body Effect of Water Clusters. University Chemistry, 2025, 40(3): 100-107. doi: 10.12461/PKU.DXHX202405074
14. [14]
  Cunming Yu , Dongliang Tian , Jing Chen , Qinglin Yang , Kesong Liu , Lei Jiang . Chemistry “101 Program” Synthetic Chemistry Experiment Course Construction: Synthesis and Properties of Bioinspired Superhydrophobic Functional Materials. University Chemistry, 2024, 39(10): 101-106. doi: 10.12461/PKU.DXHX202408008
15. [15]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
16. [16]
  Zhenming Xu , Mingbo Zheng , Zhenhui Liu , Duo Chen , Qingsheng Liu . Experimental Design of Project-Driven Teaching in Computational Materials Science: First-Principles Calculations of the LiFePO₄ Cathode Material for Lithium-Ion Batteries. University Chemistry, 2024, 39(4): 140-148. doi: 10.3866/PKU.DXHX202307022
17. [17]
  Cen Zhou , Biqiong Hong , Yiting Chen . Application of Electrochemical Techniques in Supramolecular Chemistry. University Chemistry, 2025, 40(3): 308-317. doi: 10.12461/PKU.DXHX202406086
18. [18]
  Pengcheng Yan , Peng Wang , Jing Huang , Zhao Mo , Li Xu , Yun Chen , Yu Zhang , Zhichong Qi , Hui Xu , Henan Li . Engineering Multiple Optimization Strategy on Bismuth Oxyhalide Photoactive Materials for Efficient Photoelectrochemical Applications. Acta Physico-Chimica Sinica, 2025, 41(2): 100014-. doi: 10.3866/PKU.WHXB202309047
19. [19]
  Jiaxuan Zuo , Kun Zhang , Jing Wang , Xifei Li . 锂离子电池Ni-Co-Mn基正极材料前驱体的形核调控及机制. Acta Physico-Chimica Sinica, 2025, 41(1): 2404042-. doi: 10.3866/PKU.WHXB202404042
20. [20]
  Xiufang Wang , Donglin Zhao , Kehua Zhang , Xiaojie Song . “Preparation of Carbon Nanotube/SnS₂ Photoanode Materials”: A Comprehensive University Chemistry Experiment. University Chemistry, 2024, 39(4): 157-162. doi: 10.3866/PKU.DXHX202308025

Get Citation

PDF

XML

Metrics

PDF Downloads(76)
Abstract views(5278)
HTML views(1217)

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