Supramolecular polymeric materials via cyclodextrin-guest interactions

Accounts of Chemical Research

Volumn 47, Issue 7, 2014, Pages 2128-2140

  Harada, Akira ^a,b   Takashima, Yoshinori ^a   Nakahata, Masaki ^a  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; AZOBENZENE; CYCLODEXTRIN; FERROCENE; FERROCENECARBOXYLIC ACID; FERROUS ION; HYDROGEL; MACROGOL DERIVATIVE; MACROMOLECULE; POLYMER; SOLVENT;

ARTIFICIAL ORGAN; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEL; LIGHT; MACROMOLECULE; MUSCLE; OXIDATION REDUCTION REACTION; PH; TEMPERATURE; ULTRAVIOLET RADIATION;

ARTIFICIAL ORGANS; AZO COMPOUNDS; CYCLODEXTRINS; FERROUS COMPOUNDS; HYDROGELS; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGHT; MACROMOLECULAR SUBSTANCES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MUSCLES; OXIDATION-REDUCTION; POLYETHYLENE GLYCOLS; POLYMERS; SOLVENTS; TEMPERATURE; ULTRAVIOLET RAYS;

EID: 84904430236     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500109h     Document Type: Article

References (61)

1. Pedersen, C. J. The Discovery of Crown Ethers (Noble Lecture) Angew. Chem., Int. Ed. 1988, 27, 1021-1027
2. Cram, D. J. The Design of Molecular Hosts, Guests, and Their Complexes (Nobel Lecture) Angew. Chem., Int. Ed. 1988, 27, 1009-1112
3. Lehn, J.-M. Supramolecular Chemistry-Scope and Perspectives Molecules, Supermolecules, and Molecular Devices (Nobel Lecture) Angew. Chem., Int. Ed. 1988, 27, 89-112
4. Mock, W. L. In Molecular recognition: receptors for molecular guests; Vögtle, F., Ed.; Comprehensive Supramolecular Chemistry; Pergamon: New York, 1996; Vol. 2, pp 477-494.
5. Brunsveld, L.; Folmer, B. J. B.; Meijer, E. W.; Sijbesma, R. P. Supramolecular Polymers Chem. Rev. 2001, 101, 4071-4098
6. Ciferri, A., Ed. Supramolecular Polymers, 2 nd ed.; CRC Press, Taylor and Francis: Boca Raton, FL, 2005.
7. Harada, A.; Kamachi, M. Complex Formation between Poly(ethylene glycol) and α-Cyclodextrin Macromolecules 1990, 23, 2821-2823
8. Harada, A.; Li, J.; Kamachi, M. The Molecular Necklace: A Rotaxane Containing Many Threaded α-Cyclodextrins Nature 1992, 356, 325-327
9. Harada, A. Cyclodextrins. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons, Inc.: Chichester, U.K., 1996; pp 407-432.
10. Cyclodextrins; Szejtli, J.; Osa, T., Eds.; Comprehensive Supramolecular Chemistry; Pergamon: New York, 1996; Vol. 3.
11. Harada, A.; Furue, M.; Nozakura, S.-I. Cyclodextrin-Containing Polymers. I. Preparation of Polymers Macromolecules 1976, 9, 701-704
12. Harada, A.; Adachi, H.; Kawaguchi, Y.; Kamachi, M. Recognition of Alkyl Groups on a Polymer Chain by Cyclodextrins Macromolecules 1997, 30, 5181-5182
13. Hoshino, T.; Miyauchi, M.; Kawaguchi, Y.; Yamaguchi, H.; Harada, A. Daisy Chain Necklace: Tri[2]rotaxane Containing Cyclodextrins J. Am. Chem. Soc. 2000, 122, 9876-9877
14. Raymo, F. M.; Stoddart, J. F. Interlocked Macromolecules Chem. Rev. 1999, 99, 1643-1663
15. Wenz, G.; Han, B.-H.; Mller, A. Cyclodextrin Rotaxanes and Polyrotaxanes Chem. Rev. 2006, 106, 782-817
16. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Polymeric Rotaxanes Chem. Rev. 2009, 109, 5974-6023
17. Hashidzume, A.; Tomatsu, I.; Harada, A. Interaction of Cyclodextrins with Side Chains of Water Soluble Polymers: A Simple Model for Biological Molecular Recognition and Its Utilization for Stimuli-Responsive Systems Polymer 2006, 47, 6011-6027
18. Hashidzume, A.; Ito, F.; Tomatsu, I.; Harada, A. Macromolecular Recognition by Polymer-Carrying Cyclodextrins: Interaction of a Polymer Bearing Cyclodextrin Moieties with Poly(acrylamide)s Bearing Aromatic Side Chains Macromol. Rapid Commun. 2005, 26, 1151-1154
19. Harada, A.; Ito, F.; Tomatsu, I.; Shimoda, K.; Hashidzume, A.; Takashima, Y.; Yamaguchi, H.; Kamitori, S. Spectroscopic Study on the Interaction of Cyclodextrins with Naphthyl Groups Attached to Poly(acrylamide) Backbone J. Photochem. Photobiol., A 2006, 179, 13-19
20. Hashidzume, A.; Harada, A. Macromolecular Recognition by Cyclodextrins. Interaction of Cyclodextrins with Polymethacrylamides Bearing Hydrophobic Amino Acid Residues Polymer 2006, 47, 3448-3454
21. Tomatsu, I.; Hashidzume, A.; Harada, A. Gel-to-Sol and Sol-to-Gel Transitions Utilizing the Interaction of α-Cyclodextrin with Dodecyl Side Chains Attached to a Poly(acrylic acid) Backbone Macromol. Rapid Commun. 2005, 26, 825-829
22. Tomatsu, I.; Hashidzume, A.; Harada, A. Cyclodextrin-Based Side-Chain Polyrotaxane with Unidirectional Inclusion in Aqueous Media Angew. Chem., Int. Ed. 2006, 45, 4605-4608
23. Pouliquen, G.; Amiel, C.; Tribet, C. Photoresponsive Viscosity and Host-Guest Association in Aqueous Mixtures of Poly-Cyclodextrin with Azobenzene-Modified Poly(acrylic)acid J. Phys. Chem. B 2007, 111, 5587-5595
24. Zhao, Y.-L.; Stoddart, J. F. Azobenzene-Based Light-Responsive Hydrogel System Langmuir 2009, 25, 8442-8446
25. Tomatsu, I.; Hashidzume, A.; Harada, A. Redox-Responsive Hydrogel System Using the Molecular Recognition of β-Cyclodextrin Macromol. Rapid Commun. 2006, 27, 238-241
26. Harada, A.; Takahashi, S. Preparation and Properties of Cyclodextrin Inclusion Compounds of Organometallic Complexes. Ferrocene Inclusion Compounds J. Incl. Phenom. 1984, 2, 791-798
27. Wu, J.-S.; Toda, K.; Tanaka, A.; Sanemasa, I. Association Constants of Ferrocene with Cyclodextrins in Aqueous Medium Determined by Solubility Measurements of Ferrocene Bull. Chem. Soc. Jpn. 1998, 71, 1615-1618
28. Nakahata, M.; Takashima, Y.; Yamaguchi, H.; Harada, A. Redox-Responsive Self-Healing Materials Formed from Host-Guest Polymers Nat. Commun. 2011, 2 511
29. Ritter, H.; Mondrzik, B. E.; Rehahn, M.; Gallei, M. Free Radical Homopolymerization of a Vinylferrocene/Cyclodextrin Complex in Water Beilstein J. Org. Chem. 2010, 6, 60
30. Sarvothaman, M. K.; Ritter, H. Discriminating Influence of α- and Methylated β-Cyclodextrins on Complexation and Polymerization of Diacrylate and Dimethacrylate Monomers Macromol. Rapid Commun. 2004, 25 (23) 1948-1952
31. Taura, D.; Hashidzume, A.; Okumura, Y.; Harada, A. Cooperative Complexation of α-Cyclodextrin with Alternating Copolymers of Sodium Maleate and Dodecyl Vinyl Ether with Varying Molecular Weights Macromolecules 2008, 41, 3640-3645
32. Taura, D.; Hashidzume, A.; Harada, A. Macromolecular Recognition: Interaction of Cyclodextrins with an Alternating Copolymer of Sodium Maleate and Dodecyl Vinyl Ether Macromol. Rapid Commun. 2007, 28, 2306-2310
33. Taura, D.; Taniguchi, Y.; Hashidzume, A.; Harada, A. Macromolecular Recognition of Cyclodextrin: Inversion of Selectivity of β-Cyclodextrin toward Adamantyl Groups Induced by Macromolecular Chains Macromol. Rapid Commun. 2009, 30 (20) 1741-1744
34. Taura, D.; Li, S.; Hashidzume, A.; Harada, A. Formation of Side-Chain Hetero-Polypseudorotaxane Composed of α- and β-Cyclodextrins with a Water-Soluble Polymer Bearing Two Recognition Sites Macromolecules 2010, 43, 1706-1713
35. Kretschmann, O.; Choi, S. W.; Miyauchi, M.; Tomatsu, I.; Harada, A.; Ritter, H. Switchable Hydrogels Obtained by Supramolecular Cross-Linking of Adamantyl-Containing LCST Copolymers with Cyclodextrin Dimers Angew. Chem., Int. Ed. 2006, 45, 4361-4365
36. Koopmans, C.; Ritter, H. Formation of Physical Hydrogels via Host-Guest Interactions of β-Cyclodextrin Polymers and Copolymers Bearing Adamantyl Groups Macromolecules 2008, 41, 7418-7422
37. Guo, X.; Wang, J.; Li, L.; Pham, D.-T.; Clements, P.; Lincoln, S. F.; May, B. L.; Chen, Q.; Zheng, L.; Prud'homme, R. K. Tailoring Polymeric Hydrogels through Cyclodextrin Host-Guest Complexation Macromol. Rapid Commun. 2010, 31, 300-304
38. Wang, j.; Pham, D.-T.; Guo, X.; Li, L.; Lincoln, S. F.; Luo, Z.; Ke, H.; Zheng, L.; Prud'homme, R. K. Polymeric Networks Assembled by Adamantyl and β-Cyclodextrin Substituted Poly(acrylate)s: Host-Guest Interactions, and the Effects of Ionic Strength and Extent of Substitution Ind. Eng. Chem. Res. 2010, 49, 609-612
39. Li, L.; Guo, X.; Wang, J.; Liu, P.; Prud'homme, R. K.; May, B. L.; Lincoln, S. F. Polymer Networks Assembled by Host-Guest Inclusion between Adamantyl and β-Cyclodextrin Substituents on Poly(acrylic acid) in Aqueous Solution Macromolecules 2008, 41, 8677-8681
40. Feringa, B. L. Molecular Switches; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2001.
41. Irie, M. Diarylethenes for Memories and Switches Chem. Rev. 2000, 100, 1685-1716
42. Takashima, Y.; Nakayama, T.; Miyauchi, M.; Kawaguchi, Y.; Yamaguchi, H.; Harada, A. Complex Formation and Gelation between Copolymers Containing Pendant Azobenzene Groups and Cyclodextrin Polymers Chem. Lett. 2004, 33, 890-891
43. Tomatsu, I.; Hashidzume, A.; Harada, A. Contrast Viscosity Changes upon Photoirradiation for Mixtures of Poly(acrylic acid)-Based α-Cyclodextrin and Azobenzene Polymers J. Am. Chem. Soc. 2006, 128, 2226-2227
44. Tamesue, S.; Takashima, Y.; Yamaguchi, H.; Shinkai, S.; Harada, A. Photoswitchable Supramolecular Hydrogels Formed by Cyclodextrins and Azobenzene Polymers Angew. Chem. 2010, 122 (41) 7623-7626
45. Angew. Chem., Int. Ed. 2010, 49, 41 7461-7464.
46. Bergman, S. D.; Wudl, F. Mendable Polymers J. Mater. Chem. 2008, 18, 41-62
47. Burattini, S.; Greenland, B. W.; Chappell, D.; Colquhoun, H. M.; Hayes, W. Healable Polymeric Materials: A Tutorial Review Chem. Soc. Rev. 2010, 39, 1973-1985
48. Urban, M. W., Ed. Handbook of Stimuli-Responsive Materials; Wiley-VCH Verlag GmbH & Co, KGaA: Weinheim, Germany, 2011.
49. Binder, W. H., Ed. Self-Healing Polymers: From Principles to Applications; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2013.
50. Kakuta, T.; Takashima, Y.; Nakahata, M.; Otsubo, M.; Yamaguchi, H.; Harada, A. Preorganized Hydrogel: Self-Healing Properties of Supramolecular Hydrogels Formed by Polymerization of Host-Guest-Monomers that Contain Cyclodextrins and Hydrophobic Guest Groups Adv. Mater. 2013, 25, 2849-2853
51. Harada, A.; Kobayashi, R.; Takashima, Y.; Hashidzume, A.; Yamaguchi, H. Macroscopic Self-Assembly through Molecular Recognition Nat. Chem. 2011, 3, 34-37
52. Yamaguchi, H.; Kobayashi, R.; Takashima, Y.; Hashidzume, A.; Harada, A. Self-Assembly of Gels through Molecular Recognition of Cyclodextrins: Shape Selectivity for Linear and Cyclic Guest Molecules Macromolecules 2011, 44, 2395-2399
53. Zheng, Y.; Hashidzume, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Macroscopic Observations of Molecular Recognition: Discrimination of the Substituted Position on the Naphthyl Group by Polyacrylamide Gel Modified with β-Cyclodextrin Langmuir 2011, 27, 13790-13795
54. Hashidzume, A.; Zheng, Y.; Takashima, Y.; Yamaguchi, H.; Harada, A. Macroscopic Self-Assembly Based on Molecular Recognition: Effect of Linkage between Aromatics and the Polyacrylamide Gel Scaffold, Amide versus Ester Macromolecules 2013, 46, 4575-4579
55. Yamaguchi, H.; Kobayashi, Y.; Kobayashi, R.; Takashima, Y.; Hashidzume, A.; Harada, A. Photoswitchable Gel Assembly Based on Molecular Recognition Nat. Commun. 2012, 3 603
56. Nakahata, M.; Takashima, Y.; Harada, A. Angew. Chem., Int. Ed. 2014, 53, 3617-3621
57. Zheng, Y.; Hashidzume, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Switching of Macroscopic Molecular Recognition Selectivity Using a Mixed Solvent System Nat. Commun. 2012, 3 831
58. Zheng, Y.; Hashidzume, A.; Harada, A. pH-Responsive Self-Assembly by Molecular Recognition on a Macroscopic Scale Macromol. Rapid Commun. 2013, 34, 1062-1066
59. Zheng, Y.; Hashidzume, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Temperature-Sensitive Macroscopic Assembly Based on Molecular Recognition ACS Macro Lett. 2012, 1, 1083-1085
60. Takashima, Y.; Hatanaka, S.; Otsubo, M.; Nakahata, M.; Kakuta, T.; Hashidzume, A.; Yamaguchi, H.; Harada, A. Expansion-Contraction of Photoresponsive Artificial Muscle Regulated by Host-Guest Interactions Nat. Commun. 2012, 3 1270
61. Nakahata, M.; Takashima, Y.; Hashidzume, A.; Harada, A. Redox-Generated Mechanical Motion of a Supramolecular Polymeric Actuator Based on Host-Guest Interactions Angew. Chem., Int. Ed. 2013, 52, 5731-5735