Citation: Fuji Sakai, Zhong-Wei Ji, Jiang-Hua Liu, Guo-Song Chen, Ming Jiang. A novel supramolecular graft copolymer via cucurbit[8]uril-based complexation and its self-assembly[J]. Chinese Chemical Letters, ;2013, 24(07): 568-572. shu

A novel supramolecular graft copolymer via cucurbit[8]uril-based complexation and its self-assembly

1.
State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular Sciences, Fudan University, Shanghai 200433, China

Corresponding author: Guo-Song Chen,
Received Date: 28 February 2013
Available Online: 26 March 2013

A novel supramolecular graft copolymer (SGP) composed of viologen-containing copolymer (P(DMA-co-diEV)) as the main chain and Np ended PNIPAM (Np-PNIPAm) as the grafts is prepared (DMA: N,N-dimethylacryamide, diEV: ethylviologen dimer, Np: naphthalene, PNIPAM: poly(N-isopropylacrylamide)). The grafting is based on the triple complexation among a host of cucurbit[8]uril (CB[8]) and two guests of diEV and Np, which is characterized by UV-vis spectra and ITC. Temperature sensitive property of PNIPAm moiety allows SGP to self-assemble into non-covalently connected micelle (NCCM) at high temperature. The micelles are sensitive to reducing agents, for example Na₂S₂O₃, which breaks the current inclusion complex pair and induces aggregation.
- Macromolecular self-assembly,
- Inclusion complexation,
- Thermo responsive polymer,
- Cucurbit[8]uril
1. [1]
  [1] L.Y.T. Chou, K. Ming, W.C.W. Chan, Strategies for the intracellular delivery of nanoparticles, Chem. Soc. Rev. 40 (2011) 233-245.
2. [2]
  [2] M.C. Jones, H. Gao, J.C. Leroux, Reverse polymeric micelles for pharmaceutical applications, J. Controlled Release 132 (2008) 208-215.
3. [3]
  [3] V.K. Mourya, N. Inamdar, R.B. Nawale, S.S. Kulthe, Polymeric micelles: general considerations and their applications, Indian J. Pharm. Edu. Res. 45 (2011) 128-138.
4. [4]
  [4] D. Chen, M. Jiang, Strategies for constructing polymeric micelles and hollow spheres in solution via specific intermolecular interactions, Acc. Chem. Res. 38 (2005) 494-502.
5. [5]
  [5] M. Guo, M. Jiang, Non-covalently connected micelles (NCCMs): the origins and development of a new concept, Soft Matter 5 (2009) 495-500.
6. [6]
  [6] G. Chen, M. Jiang, Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly, Chem. Soc. Rev. 40 (2011) 2254-2266.
7. [7]
  [7] L. Su, Y. Zhao, G. Chen, M. Jiang, Polymeric vesicles mimicking glycocalyx (PV-Gx) for studying carbohydrate-protein interactions in solution, Polym. Chem. 3 (2012) 1560-1566.
8. [8]
  [8] A.O. Moughton, R.K. O'Reilly, Noncovalently connected micelles, nanoparticles, and metal-functionalized nanocages using supramolecular self-assembly, J. Am. Chem. Soc. 130 (2008) 8714-8725.
9. [9]
  [9] Q. Yan, J. Yuan, Z. Cai, et al., Voltage-responsive vesicles based on orthogonal assembly of two homopolymers, J. Am. Chem. Soc. 132 (2010) 9268-9270.
10. [10]
  [10] J. Zou, F. Tao, M. Jiang, Optical switching of self-assembly and disassembly of noncovalently connected amphiphiles, Langmuir 23 (2007) 12791-12794.
11. [11]
  [11] Z.J. Ding, H.Y. Zhang, L.H. Wang, F. Ding, Y. Liu, A heterowheel [3]pseudorotaxane by intergrating b-cyclodextrin and cucurbit[8]uril inclusion complexes, Org. Lett. 13 (2011) 856-859.
12. [12]
  [12] (a) A.I. Day, R.J. Blanch, A.P. Arnold, et al., A cucurbituril-based gyroscane: a new supramolecular form, Angew. Chem. Int. Ed. 41 (2002) 275-277;
13. [13]
  (b) C. Marquez, F. Huang, W.M. Nau, Cucurbiturils: molecular nanocapsules for time-resolved fluorescence-based assays, IEEE Trans. Nanobiosci. 3 (2004) 39-45.
14. [14]
  [13] J. Kim, I.S. Jung, S.Y. Kim, et al., New cucurbituril homologues: syntheses, isolation, characterization, and X-ray crystal structures of cucurbit[n]uril (n=5, 7, and 8), J. Am. Chem. Soc. 122 (2000) 540-541.
15. [15]
  [14] (a) X. Fu, Y. Huang, Z. Tao, et al., Investigation of cucurbit[6,7,8]urils with adefovir bis(L-amino acid) ester prodrug and its anti-HBV activity, Chin. J. Org. Chem. 30 (2010) 675-683;
16. [16]
  (b) P. Li, L. Li, et al., Application of organic macrocyclic supramolecular structures on adsorption and conversion of carbon dioxide, Prog. Chem. 22 (2010) 1940-1951.
17. [17]
  [15] Y.H. Ko, E. Kim, I. Hwang, Supramolecular assemblies built with host-stabilized charge-transfer interactions, Chem. Commun. (2007) 1305-1315.
18. [18]
  [16] U. Rauwald, O.A. Scherman, Supramolecular block copolymers with cucurbit[8]uril in water, Angew. Chem. Int. Ed. 47 (2008) 3950-3953.
19. [19]
  [17] X.J. Loh, J. del Barrio, P.P.C. Toh, et al., Triply triggered doxorubicin release from supramolecular nanocontainers, Biomacromolecules 13 (2012) 84-91.
20. [20]
  [18] Y. Liu, R. Fang, X. Tan, et al., Supramolecular polymerization at low monomer concentrations: enhancing intermolecular interactions and suppressing cyclization by rational molecular design, Chem. Eur. J. 18 (2012) 15650-15654.
21. [21]
  [19] Y. Liu, K. Liu, Z. Wang, et al., Host-enhanced π-π interaction for water-soluble supramolecular polymerization, Chem. Eur. J. 17 (2011) 9930-9935.
22. [22]
  [20] Y. Liu, Y. Yu, J. Gao, et al., Water-soluble supramolecular polymerization driven by multiple host-stabilized charge-transfer interactions, Angew. Chem. 122 (2010) 6726-6729.
23. [23]
  [21] C.J. Chen, D.D. Li, H.B. Wang, et al., Fabrication of dual-responsive micelles based on the supramolecular interaction of cucurbit[8]uril, Polym. Chem. 4 (2013) 242-245.
24. [24]
  [22] E.A. Appel, F. Biedermann, U. Rauwald, et al., Supramolecular cross-linked networks via host-guest complexation with cucurbit[8]uril, J. Am. Chem. Soc. 132 (2010) 14251-14260.
25. [25]
  [23] C. Wu, X. Wang, Globule-to-coil transition of a single homopolymer chain in solution, Phys. Rev. Lett. 80 (1998) 4092-4094.
26. [26]
  [24] T. Noda, Y. Morishima, Hydrophobic association of random copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and dodecyl methacrylate in water as studied by fluorescence and dynamic light scattering, Macromolecules 32 (1999) 4631-4640.
27. [27]
  [25] S.I. Yusa, M. Kamachi, Y. Morishima, Hydrophobic self-association of cholesterol moieties covalently linked to polyelectrolytes: effect of spacer bond, Langmuir 14 (1998) 6059-6067.
28. [28]
  [26] J.W. Lee, I. Hwang, W.S. Jeon, et al., Synthetic molecular machine based on reversible end-to-interior and end-to-end loop formation triggered by electrochemical stimuli, Chem. Asian J. 3 (2008) 1277-1283.
29. [29]
  [27] W.S. Jeon, H.J. Kim, C. Lee, et al., Control of the stoichiometry in host-guest complexation by redox chemistry of guests: inclusion of methylviologen in cucurbit[8]uril, Chem. Commun. (2002) 1828-1829.
1. [1]
  Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
2. [2]
  Shaojie Deng , Peihua Ma , Qinghong Bai , Xin Xiao . The transformation of nor-seco-cucurbit[10]uril to cucurbit[5]uril and cucurbit[8]uril controlled by its own concentration. Chinese Chemical Letters, 2025, 36(2): 109878-. doi: 10.1016/j.cclet.2024.109878
3. [3]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
4. [4]
  Bing Niu , Honggao Huang , Liwei Luo , Li Zhang , Jianbo Tan . Coating colloidal particles with a well-defined polymer layer by surface-initiated photoinduced polymerization-induced self-assembly and the subsequent seeded polymerization. Chinese Chemical Letters, 2025, 36(2): 110431-. doi: 10.1016/j.cclet.2024.110431
5. [5]
  Ran Cen , Yan-Yan Tang , Li-Xia Chen , Zhu Tao , Xin Xiao . A novel supramolecular assembly based on nor-seco-cucurbit[10]uril for spermine sensing and artificial light-harvesting. Chinese Chemical Letters, 2025, 36(1): 109744-. doi: 10.1016/j.cclet.2024.109744
6. [6]
  Hao Zhang , Haonan Qu , Ehsan Bahojb Noruzi , Haibing Li , Feng Liang . A nanocomposite film with layer-by-layer self-assembled gold nanospheres driven by cucurbit[7]uril for the selective transport of L-tryptophan and lysozyme. Chinese Chemical Letters, 2025, 36(1): 109731-. doi: 10.1016/j.cclet.2024.109731
7. [7]
  Jianqiu Li , Yi Zhang , Songen Liu , Jie Niu , Rong Zhang , Yong Chen , Yu Liu . Cucurbit[8]uril-based non-covalent heterodimer realized NIR cell imaging through topological transformation from nanowire to nanorod. Chinese Chemical Letters, 2024, 35(10): 109645-. doi: 10.1016/j.cclet.2024.109645
8. [8]
  Yu Xia , Yangming Jiang , Xin-Long Ni , Qiaochun Wang , Daoping Wang . A macrocycle-based "Russian doll": The smallest cucurbit[4]uril in cucurbit[10]uril. Chinese Chemical Letters, 2024, 35(12): 109782-. doi: 10.1016/j.cclet.2024.109782
9. [9]
  Zhenzhu Wang , Chenglong Liu , Yunpeng Ge , Wencan Li , Chenyang Zhang , Bing Yang , Shizhong Mao , Zeyuan Dong . Differentiated self-assembly through orthogonal noncovalent interactions towards the synthesis of two-dimensional woven supramolecular polymers. Chinese Chemical Letters, 2024, 35(5): 109127-. doi: 10.1016/j.cclet.2023.109127
10. [10]
  Sifan Du , Yuan Wang , Fulin Wang , Tianyu Wang , Li Zhang , Minghua Liu . Evolution of hollow nanosphere to microtube in the self-assembly of chiral dansyl derivatives and inversed circularly polarized luminescence. Chinese Chemical Letters, 2024, 35(7): 109256-. doi: 10.1016/j.cclet.2023.109256
11. [11]
  Cheng-Yan Wu , Yi-Nan Gao , Zi-Han Zhang , Rui Liu , Quan Tang , Zhong-Lin Lu . Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages. Chinese Chemical Letters, 2024, 35(11): 109649-. doi: 10.1016/j.cclet.2024.109649
12. [12]
  Lijun Mao , Shuo Li , Xin Zhang , Zhan-Ting Li , Da Ma . Cucurbit[n]uril-based nanostructure construction and modification. Chinese Chemical Letters, 2024, 35(8): 109363-. doi: 10.1016/j.cclet.2023.109363
13. [13]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
14. [14]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
15. [15]
  Changhui Yu , Peng Shang , Huihui Hu , Yuening Zhang , Xujin Qin , Linyu Han , Caihe Liu , Xiaohan Liu , Minghua Liu , Yuan Guo , Zhen Zhang . Evolution of template-assisted two-dimensional porphyrin chiral grating structure by directed self-assembly using chiral second harmonic generation microscopy. Chinese Chemical Letters, 2024, 35(10): 109805-. doi: 10.1016/j.cclet.2024.109805
16. [16]
  Yi Zhou , Wei Zhang , Rong Fu , Jiaxin Dong , Yuxuan Liu , Zihang Song , Han Han , Kang Cai . Self-assembly of two pairs of homochiral M₂L₄ coordination capsules with varied confined space using Tröger's base ligands. Chinese Chemical Letters, 2025, 36(2): 109865-. doi: 10.1016/j.cclet.2024.109865
17. [17]
  Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
18. [18]
  Chun-Yun Ding , Ru-Yuan Zhang , Yu-Wu Zhong , Jiannian Yao . Binary and heterostructured microplates of iridium and ruthenium complexes: Preparation, characterization, and thermo-responsive emission. Chinese Journal of Structural Chemistry, 2024, 43(10): 100393-100393. doi: 10.1016/j.cjsc.2024.100393
19. [19]
  Xingwen Cheng , Haoran Ren , Jiangshan Luo . Boosting the self-trapped exciton emission in vacancy-ordered double perovskites via supramolecular assembly. Chinese Journal of Structural Chemistry, 2024, 43(6): 100306-100306. doi: 10.1016/j.cjsc.2024.100306
20. [20]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(622)
HTML views(1)

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