Supramolecular polymers constructed from macrocycle-based host-guest molecular recognition motifs

Accounts of Chemical Research

Volumn 47, Issue 7, 2014, Pages 1982-1994

  Dong, Shengyi ^a   Zheng, Bo ^a   Wang, Feng ^a   Huang, Feihe ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84904431155     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar5000456     Document Type: Article

References (56)

1. De Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A. P. H. J.; Sijbesma, R. P.; Meijer, E. W. Supramolecular polymerization Chem. Rev. 2009, 109, 5687-5754
2. Guo, D.-S.; Liu, Y. Calixarene-based supramolecular polymerization in solution Chem. Soc. Rev. 2012, 41, 5907-5921
3. Fouquey, C.; Lehn, J.-M.; Levelut, A.-M. Molecular recognition directed self-assembly of supramolecular liquid crystalline polymers from complementary chiral components Adv. Mater. 1990, 2, 254-257
4. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; Wiley-VCH: Weinheim, Germany, 1995.
5. Wojtecki, R. J.; Meador, M. A.; Rowan, S. J. Using the dynamic bond to access macroscopically responsive structurally dynamic polymers Nat. Mater. 2011, 10, 14-27
6. Miyauchi, M.; Takashima, Y.; Yamaguchi, H.; Harada, A. Chiral supramolecular polymers formed by host-guest interactions J. Am. Chem. Soc. 2005, 127, 2984-2989
7. Niu, Z.; Gibson, H. W. Polycatenanes Chem. Rev. 2009, 109, 6024-6046
8. Nepogodiev, S. A.; Stoddart, J. F. Cyclodextrin-based catenanes and rotaxanes Chem. Rev. 1998, 98, 1959-1976
9. Ma, X.; Tian, H. Bright functional rotaxanes Chem. Soc. Rev. 2010, 39, 70-80
10. Liu, S.; Zavalij, P. Y.; Isaacs, L. Cucurbit[10]uril J. Am. Chem. Soc. 2005, 127, 16798-16799
11. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Cucurbituril homologues and derivatives: New opportunities in supramolecular chemistry Acc. Chem. Res. 2003, 36, 621-630
12. Xue, M.; Yang, Y.; Chi, X.; Zhang, Z.; Huang, F. Pillararenes, a new class of macrocycles for supramolecular chemistry Acc. Chem. Res. 2012, 45, 1294-1308
13. Zhang, C.; Li, S.; Zhang, J.; Zhu, K.; Li, N.; Huang, F. Benzo-21-crown-7/secondary dialkylammonium salt [2]pseudorotaxane- and [2]rotaxane-type threaded structures Org. Lett. 2007, 9, 5553-5556
14. Loeb, S. J.; Wisner, J. A. A new motif for the self-assembly of [2]pseudorotaxanes; 1,2-Bis(byridinium)ethane axles and [24]crown-8 ether wheels Angew. Chem., Int. Ed. 1998, 37, 2838-2840
15. Zhang, Z.; Xia, B.; Han, C.; Yu, Y.; Huang, F. Syntheses of copillar[5]arenes by co-oligomerization of different monomers Org. Lett. 2010, 12, 3285-3287
16. Joseph, R.; Rao, C. P. Ion and molecular recognition by lower rim 1,3-di-conjugates of calix[4]arene as receptors Chem. Rev. 2011, 111, 4658-4702
17. Mock, W. L.; Shih, N.-Y. Organic ligand-receptor interactions between cucurbituril and alkylammonium ions J. Am. Chem. Soc. 1988, 110, 4706-4710
18. Zheng, B.; Wang, F.; Dong, S.; Huang, F. Supramolecular polymers constructed by crown ether-based molecular recognition Chem. Soc. Rev. 2012, 41, 1621-1636
19. Yan, X.; Wang, F.; Zheng, B.; Huang, F. Stimuli-responsive supramolecular polymeric materials Chem. Soc. Rev. 2012, 41, 6042-6065
20. Buerkle, L. E.; Rowan, S. J. Supramolecular gels formed from multi-component low molecular weight species Chem. Soc. Rev. 2012, 41, 6089-6102
21. Ashton, P. R.; Parsons, I. W.; Raymo, F. M.; Stoddart, J. F.; White, A. J. P.; Williams, D. J.; Wolf, R. Self-assembling supramolecular daisy chains Angew. Chem., Int. Ed. 1998, 37, 1913-1916
22. Ashton, P. R.; Baxter, I.; Cantrill, S. J.; Fyfe, M. C. T.; Glink, P. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Supramolecular daisy chains Angew. Chem., Int. Ed. 1998, 37, 1294-1297
23. Gibson, H. W.; Yamaguchi, N.; Niu, Z.; Jones, J. W.; Slebodnick, C.; Rheingold, A. L.; Zakharov, L. N. Self-assembly of daisy chain oligomers from heteroditopic molecules containing secondary ammonium ion and crown ether moieties J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 975-985
24. Huang, F.; Nagvekar, D. S.; Zhou, X.; Gibson, H. W. Formation of a linear supramolecular polymer by self-assembly of two homoditopic monomers based on the bis(m -phenylene)-32-crown-10/paraquat recognition motif Macromolecules 2007, 40, 3561-3567
25. Yamaguchi, N.; Gibson, H. W. Stabilities of cooperatively formed pseudorotaxane dimmers J. Chem. Soc., Chem. Commun. 1999, 789-790
26. Gibson, H. W.; Yamaguchi, N.; Jones, J. W. Supramolecular pseudorotaxane polymers from complementary pairs of homoditopic molecules J. Am. Chem. Soc. 2003, 125, 3522-3533
27. Wang, F.; Han, C.; He, C.; Zhou, Q.; Zhang, J.; Wang, C.; Li, N.; Huang, F. Self-sorting organization of two heteroditopic monomers to supramolecular alternating copolymers J. Am. Chem. Soc. 2008, 130, 11254-11255
28. Wang, F.; Zhang, J.; Ding, X.; Dong, S.; Liu, M.; Zheng, B.; Li, S.; Wu, L.; Yu, Y.; Gibson, H. W.; Huang, F. Metal coordination mediated reversible conversion between linear and cross-linked supramolecular polymers Angew. Chem., Int. Ed. 2010, 49, 1090-1094
29. Dong, S.; Luo, Y.; Yan, X.; Zheng, B.; Ding, X.; Yu, Y.; Ma, Z.; Zhao, Q.; Huang, F. A dual-responsive supramolecular polymer gel formed by crown ether based molecular recognition Angew. Chem., Int. Ed. 2011, 50, 1905-1909
30. Yan, X.; Zhou, M.; Chen, J.; Chi, X.; Dong, S.; Zhang, M.; Ding, X.; Yu, Y.; Shao, S.; Huang, F. Supramolecular polymer nanofibers via electrospinning of a heteroditopic monomer Chem. Commun. 2011, 47, 7086-7088
31. Chen, J.; Yan, X.; Zhao, Q.; Li, L.; Huang, F. Adjustable supramolecular polymer microstructures fabricated by the breath figure method Polym. Chem. 2012, 3, 458-462
32. Yan, X.; Xu, D.; Chi, X.; Chen, J.; Dong, S.; Ding, X.; Yu, Y.; Huang, F. A multiresponsive, shape-persistent, and elastic supramolecular polymer network gel constructed by orthogonal self-assembly Adv. Mater. 2012, 24, 362-369
33. Yan, X.; Xu, D.; Chen, J.; Zhang, M.; Hu, B.; Yu, Y.; Huang, F. A self-healing supramolecular polymer gel with stimuli-responsiveness constructed by crown ether based molecular recognition Polym. Chem. 2013, 4, 3312-3322
34. Deng, W.; Yamaguchi, H.; Takashima, Y.; Harada, A. A chemical-responsive supramolecular hydrogel from modified cyclodextrins Angew. Chem., Int. Ed. 2007, 46, 5144-5147
35. Tamesue, S.; Takashima, Y.; Yamaguchi, H.; Shinkai, S.; Harada, A. Photoswitchable supramolecular hydrogels formed by cyclodextrins and azobenzene polymers Angew. Chem., Int. Ed. 2010, 49, 7461-7464
36. Zhu, L.; Lu, M.; Zhang, Q.; Qu, D.; Tian, H. Construction of polypseudorotaxane from low-molecular weight monomers via dual nancovalent interactions Macromolecules 2011, 44, 4092-4097
37. Sun, R.; Xue, C.; Ma, X.; Gao, M.; Tian, H.; Li, Q. Light-driven linear helical supramolecular polymer formed by molecular-recognition-directed self-assembly of bis(p -sulfonatocalix[4]arene) and pseudorotaxane J. Am. Chem. Soc. 2013, 135, 5990-5993
38. Tellini, V. H. S.; Jover, A.; García, J. C.; Galantini, L.; Meijide, F.; Tato, J. V. Thermodynamics of formation of host-guest supramolecular polymers J. Am. Chem. Soc. 2006, 128, 5728-5734
39. Leggio, C.; Anselmi, M.; Nola, A. D.; Galantini, L.; Jover, A.; Meijide, F.; Pavel, N. V.; Tellini, V. H. S.; Tato, J. V. Study on the structure of host-guest supramolecular polymers Macromolecules 2007, 40, 5899-5906
40. Pappalardo, S.; Villari, V.; Slovak, S.; Cohen, Y.; Gattuso, G.; Notti, A.; Pappalardo, A.; Pisagatti, I.; Parisi, M. F. Counterion-dependent proton-driven self-assembly of linear supramolecular oligomers based on amino-calix[5]arene building blocks Chem.-Eur. J. 2007, 13, 8164-8173
41. Qian, H.; Guo, D.-S.; Liu, Y. Cucurbituril-modulated supramolecular assemblies: from cyclic oligomers to linear polymers Chem.-Eur. J. 2012, 18, 5087-5095
42. Guo, D.-S; Chen, S.; Qian, -H.; Zhang, H.-Q; Liu, Y. Electrochemical stimulus-responsive supramolecular polymer based on sulfonatocalixarene and viologen dimers Chem. Commun. 2010, 46, 2620-2622
43. Yebeutchou, R. M.; Tancini, F.; Demitri, N.; Geremia, S.; Mendichi, R.; Dalcanale, E. Host-guest driven self-assembly of linear and star supramolecular polymers Angew. Chem., Int. Ed. 2008, 47, 4504-4508
44. Kim, K.; Kim, D.; Lee, J. W.; Ko, Y. H.; Kim, K. Growth of poly(pseudorotaxane) on gold using host-stabilized charge-transfer interaction Chem. Commun. 2004, 848-849
45. Liu, Y.; Liu, K.; Wang, Z.; Zhang, X. Host-enhanced π-π interaction for water-soluble supramolecular polymerization Chem.-Eur. J. 2011, 17, 9930-9935
46. Liu, Y.; Yu, Y.; Gao, J.; Wang, Z.; Zhang, X. Water-soluble supramolecular polymerization driven by multiple host-stabilized charge-transfer interactions Angew. Chem., Int. Ed. 2010, 49, 6576-6579
47. Barrio, J.; Horton, P. N.; Lairez, D.; Lloyd, G. O.; Toprakcioglu, C.; Scherman, O. A. Photocontrol over cucurbit[8]uril complexes: Stoichiometry and supramolecular polymers J. Am. Chem. Soc. 2013, 135, 11760-11763
48. Zhang, K.-D.; Tian, J.; Hanifi, D.; Zhang, Y.; Sue, A. C.-H.; Zhou, T.-Y.; Zhang, L.; Zhao, X.; Liu, Y.; Li, Z.-T. Toward a single-layer two-dimensional honeycomb supramolecular organic framework in water J. Am. Chem. Soc. 2013, 135, 17913-17918
49. Liu, Y.; Yang, H.; Wang, Z.; Zhang, X. Cucurbit[8]uril-based supramolecular polymers Chem.-Asian J. 2013, 8, 1626-1632
50. Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F. Formation of linear supramolecular polymers that is driven by C-H···π interactions in solution and in the solid state Angew. Chem., Int. Ed. 2011, 50, 1397-1401
51. Xia, B.; Zheng, B.; Han, C.; Dong, S.; Zhang, M.; Hu, B.; Yu, Y.; Huang, F. A novel pH-responsive supramolecular polymer constructed by pillar[5]arene-based host-guest interactions Polym. Chem. 2013, 4, 2019-2024
52. Ogoshi, T.; Kayama, H.; Yamafuji, D.; Aoki, T.; Yamagishi, T.-a Supramolecular polymers with alternating pillar[5]arene and pillar[6]arene units from a highly selective multiple host-guest complexation system and monofunctionalized pillar[6]arene Chem. Sci. 2012, 3, 3221-3226
53. Hu, X.-Y.; Zhang, P.; Wu, X.; Xia, W.; Xiao, T.; Jiang, J.; Lin, C.; Wang, L. Pillar[5]arene-based supramolecular polypseudorotaxanes constructed from quadruple hydrogen bonding Polym. Chem. 2012, 3, 3060-3063
54. Guan, Y.; Ni, M.; Hu, X.; Xiao, T.; Xiong, S.; Lin, C.; Wang, L. Pillar[5]arene-based polymeric architectures constructed by orthogonal supramolecular interactions Chem. Commun. 2012, 48, 8529-8531
55. Wang, K.; Wang, C.-Y.; Wang, Y.; Li, H.; Bao, C.-Y.; Liu, J.-Y.; Zhang, S. X.-A.; Yang, Y.-W. Electrospun nanofibers and multi-responsive supramolecular assemblies constructed from a pillar[5]arene-based receptor Chem. Commun. 2013, 49, 10528-10530
56. Wang, X.; Han, K.; Li, J.; Jia, X.; Li, C. Pillar[5]arene-neutral guest recognition based supramolecular alternating copolymer containing [ c 2]daisy chain and bis-pillar[5]arene units Polym. Chem. 2013, 4, 3998-4003