Multiresponsive Supramolecular Gel Based on Pillararene-Containing Polymers

Macromolecules

Volumn 49, Issue 7, 2016, Pages 2814-2820

  Chang, Junxia ^a   Zhao, Qiuhua ^a   Kang, Le ^a   Li, Haimei ^a   Xie, Meiran ^a   Liao, Xiaojuan ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; ESTERS; FREE RADICALS; SOLS;

FREE RADICAL COPOLYMERIZATION; GUEST MOLECULES; HOST-GUEST COMPLEXATIONS; METHYL METHACRYLATES; MULTI-RESPONSIVE; ORDERED STACKING; PENDANT GROUPS; TEMPERATURE CHANGES;

SUPRAMOLECULAR CHEMISTRY;

EID: 84964725589     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.6b00270     Document Type: Article

References (63)

1. Yan, X.; Wang, F.; Zheng, B.; Huang, F. Stimuli-Responsive Supramolecular Polymeric Materials Chem. Soc. Rev. 2012, 41, 6042-6065 10.1039/c2cs35091b
2. 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 10.1038/nmat2891
3. Ma, X.; Tian, H. Stimuli-Responsive Supramolecular Polymers in Aqueous Solution Acc. Chem. Res. 2014, 47, 1971-1981 10.1021/ar500033n
4. 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 10.1002/anie.201006999
5. Xia, W.; Ni, M.; Yao, C.; Wang, X.; Chen, D.; Lin, C.; Hu, X.; Wang, L. Responsive Gel-like Supramolecular Network Based on Pillar[6]arene-Ferrocenium Recognition Motifs in Polymeric Matrix Macromolecules 2015, 48, 4403-4409 10.1021/acs.macromol.5b00889
6. Phadke, A.; Zhang, C.; Arman, B.; Hsu, C.-C.; Mashelkar, R. A.; Lele, A. K.; Tauber, M. J.; Arya, G.; Varghese, S. Rapid Self-Healing Hydrogels Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 4383-4388 10.1073/pnas.1201122109
7. Roy, D.; Cambre, J. N.; Sumerlin, B. S. Future Perspectives and Recent Advances in Stimuli-Responsive Materials Prog. Polym. Sci. 2010, 35, 278-301 10.1016/j.progpolymsci.2009.10.008
8. He, C. L.; Kim, S. W.; Lee, D. S. In situ Gelling Stimuli-Sensitive Block Copolymer Hydrogels for Drug Delivery J. Controlled Release 2008, 127, 189-207 10.1016/j.jconrel.2008.01.005
9. Bromberg, L. E.; Ron, E. S. Temperature-Responsive Gels and Thermogelling Polymer Matrices for Protein and Peptide Delivery Adv. Drug Delivery Rev. 1998, 31, 197-221 10.1016/S0169-409X(97)00121-X
10. Qiu, Y.; Park, K. Environment-Sensitive Hydrogels for Drug Delivery Adv. Drug Delivery Rev. 2001, 53, 321-339 10.1016/S0169-409X(01)00203-4
11. Peng, F.; Li, G.; Liu, X.; Wu, S.; Tong, Z. Redox-Responsive Gel-Sol/Sol-Gel Transition in Poly(acrylic acid) Aqueous Solution Containing Fe(III) Ions Switched by Light J. Am. Chem. Soc. 2008, 130, 16166-16167 10.1021/ja807087z
12. Ahn, S.-K.; Kasi, R. M.; Kim, S.-C.; Sharma, N.; Zhou, Y. Stimuli-Responsive Polymer Gels Soft Matter 2008, 4, 1151-1157 10.1039/b714376a
13. Yamaguchi, N.; Gibson, H. W. Formation of Supramolecular Polymers from Homoditopic Molecules Containing Secondary Ammonium Ions and Crown Ether Moieties Angew. Chem., Int. Ed. 1999, 38, 143-146 10.1002/(SICI)1521-3773(19990115)38:1/2<143::AID-ANIE143>3.0.CO;2-Y
14. Huang, F.; Nagvekar, D. S.; Slebodnick, C.; Gibson, H. W. A Supramolecular Triarm Star Polymer from a Homotritopic Tris(Crown Ether) Host and a Complementary Monotopic Paraquat-Terminated Polystyrene Guest by a Supramolecular Coupling Method J. Am. Chem. Soc. 2005, 127, 484-485 10.1021/ja0438516
15. 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 10.1021/ja8035465
16. Harada, A.; Takashima, Y.; Yamaguchi, H. Cyclodextrin-Based Supramolecular Polymers Chem. Soc. Rev. 2009, 38, 875-882 10.1039/b705458k
17. 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 10.1002/adma.201103220
18. Liu, Y.; Li, L.; Fan, Z.; Zhang, H.; Wu, X.; Guan, X.; Liu, S. Supramolecular Aggregates Formed by Intermolecular Inclusion Complexation of Organo-Selenium Bridged Bis(cyclodextrin)s with Calix[4]arene Derivative Nano Lett. 2002, 2, 257-261 10.1021/nl015670x
19. Ji, X. F.; Dong, S. Y.; Wei, P. F.; Xia, D. Y.; Huang, F. H. A Novel Diblock Copolymer with a Supramolecular Polymer Block and a Traditional Polymer Block: Preparation, Controllable Self-Assembly in Water, and Application in Controlled Release Adv. Mater. 2013, 25, 5725-5729 10.1002/adma.201301654
20. Zhang, M. M.; Xu, D. H.; Yan, X. Z.; Chen, J. Z.; Dong, S. Y.; Zheng, B.; Huang, F. H. Self-Healing Supramolecular Gels Formed by Crown Ether Based Host-Guest Interactions Angew. Chem., Int. Ed. 2012, 51, 7011-7015 10.1002/anie.201203063
21. Wang, F.; Zheng, B.; Zhu, K. L.; Zhou, Q. Z.; Zhai, C. X.; Li, S. J.; Li, N.; Huang, F. H. Formation of Linear Main-Chain Polypseudorotaxanes with Supramolecular Polymer Backbones via Two Self-Sorting Host-Guest Recognition Motifs Chem. Commun. 2009, 29, 4375-4377 10.1039/b905837k
22. Liu, J. H.; Chen, G. S.; Guo, M. Y.; Jiang, M. Dual Stimuli-Responsive Supramolecular Hydrogel Based on Hybrid Inclusion Complex (HIC) Macromolecules 2010, 43, 8086-8093 10.1021/ma101437k
23. Ji, X. F.; Yao, Y.; Li, J. Y.; Yan, X. Z.; Huang, F. H. A Supramolecular Cross-Linked Conjugated Polymer Network for Multiple Fluorescent Sensing J. Am. Chem. Soc. 2013, 135, 74-77 10.1021/ja3108559
24. Harada, A.; Takashima, Y.; Nakahata, M. Supramolecular Polymeric Materials via Cyclodextrin-Guest Interactions Acc. Chem. Res. 2014, 47, 2128-2140 10.1021/ar500109h
25. Inoue, Y.; Kuad, P.; Okumura, Y.; Takashima, Y.; Yamaguchi, H.; Harada, A. Thermal and Photochemical Switching of Conformation of Poly(ethylene glycol)-Substituted Cyclodextrin with an Azobenzene Group at the Chain End J. Am. Chem. Soc. 2007, 129, 6396-6397 10.1021/ja071717q
26. Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. para-Bridged Symmetrical Pillar[5]arenes: Their Lewis Acid Catalyzed Synthesis and Host-Guest Property J. Am. Chem. Soc. 2008, 130, 5022-5023 10.1021/ja711260m
27. Zhang, Z. B.; Luo, Y.; Chen, J. Z.; Dong, S. Y.; Yu, Y. H.; Ma, Z.; Huang, F. H. Formation of Linear Supramolecular Polymers That Is Driven by CH···π Interactions in Solution and in the Solid State Angew. Chem., Int. Ed. 2011, 50, 1397-1401 10.1002/anie.201006693
28. Li, C.; Xu, Q.; Li, J.; Yao, F.; Jia, X. Complex Interactions of Pillar[5]arene with Paraquats and Bis(pyridinium) Derivatives Org. Biomol. Chem. 2010, 8, 1568-1576 10.1039/b920146g
29. Li, C.; Shu, X.; Li, J.; Chen, S.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Complexation of 1,4-Bis(pyridinium)butanes by Negatively Charged Carboxylatopillar[5]arene J. Org. Chem. 2011, 76, 8458-8465 10.1021/jo201185e
30. Chi, X.; Xue, M.; Yao, Y.; Huang, F. Redox-Responsive Complexation between a Pillar[5]arene with Mono(ethylene oxide) Substituents and Paraquat Org. Lett. 2013, 15, 4722-4725 10.1021/ol402048n
31. Li, C.; Zhao, L.; Li, J.; Ding, X.; Chen, S.; Zhang, Q.; Yu, Y.; Jia, X. Self-assembly of [2]Pseudorotaxanes Based on Pillar[5]arene and Bis(imidazolium) Cations Chem. Commun. 2010, 46, 9016-9018 10.1039/c0cc03575k
32. Dong, S.; Zheng, B.; Yao, Y.; Han, C.; Yuan, J.; Antonietti, M.; Huang, F. LCST-Type Phase Behavior Induced by Pillar[5]arene/Ionic Liquid Host-Guest Complexation Adv. Mater. 2013, 25, 6864-6867 10.1002/adma.201303652
33. Duan, Q.; Cao, Y.; Li, Y.; Hu, X.; Xiao, T.; Lin, C.; Pan, Y.; Wang, L. pH-Responsive Supramolecular Vesicles Based on Water-Soluble Pillar[6]arene and Ferrocene Derivative for Drug Delivery J. Am. Chem. Soc. 2013, 135, 10542-10549 10.1021/ja405014r
34. Ogoshi, T.; Hashizume, M.; Yamagishi, T.; Nakamoto, Y. Synthesis, Conformational and Host-Guest Properties of Water-Soluble Pillar[5]arene Chem. Commun. 2010, 46, 3708-3710 10.1039/c0cc00348d
35. Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Novel Neutral Guest Recognition and Interpenetrated Complex Formation from Pillar[5]arenes Chem. Commun. 2011, 47, 11294-11296 10.1039/c1cc14829j
36. Shu, X.; Fan, J.; Li, J.; Wang, X.; Chen, W.; Jia, X.; Li, C. Complexation of Neutral 1,4-Dihalobutanes with Simple Pillar[5]arenes that is Dominated by Dispersion Forces Org. Biomol. Chem. 2012, 10, 3393-3397 10.1039/c2ob25251a
37. Shu, X.; Chen, S.; Li, J.; Chen, Z.; Weng, L.; Jia, X.; Li, C. Highly Effective Binding of Neutral Dinitriles by Simple Pillar[5]arenes Chem. Commun. 2012, 48, 2967-2969 10.1039/c2cc00153e
38. Li, C.; Ma, J.; Zhao, L.; Zhang, Y.; Yu, Y.; Shu, X.; Li, J.; Jia, X. Molecular Selective Binding of Basic Amino Acids by a Water-Soluble Pillar[5]arene Chem. Commun. 2013, 49, 1924-1926 10.1039/c3cc38622h
39. Wei, T.; Li, H.; Zhu, Y.; Lu, T.; Shi, B.; Lin, Q.; Yao, H.; Zhang, Y. Copillar[5]arene-based Supramolecular Polymer Gel: Controlling Stimuli-Response Properties through a Novel Strategy with Surfactant RSC Adv. 2015, 5, 60273-60278 10.1039/C5RA09253A
40. Yu, G.; Jie, K.; Huang, F. Supramolecular Amphiphiles Based on Host-Guest Molecular Recognition Motifs Chem. Rev. 2015, 115, 7240-7303 10.1021/cr5005315
41. Song, N.; Yang, Y. Applications of pillarenes, an Emerging Class of Synthetic Macrocycles Sci. China: Chem. 2014, 57, 1185-1198 10.1007/s11426-014-5190-z
42. Li, C.; Han, K.; Li, J.; Zhang, Y.; Chen, W.; Yu, Y.; Jia, X. Supramolecular Polymers Based on Efficient Pillar[5]arene-Neutral Guest Motifs Chem.-Eur. J. 2013, 19, 11892-11897 10.1002/chem.201301022
43. Hu, X.; Wu, X.; Wang, S.; Chen, D.; Xia, W.; Lin, C.; Pan, Y.; Wang, L. Pillar[5]arene-based Supramolecular Polypseudorotaxane Polymer Networks Constructed by Orthogonal Self-assembly Polym. Chem. 2013, 4, 4292-4297 10.1039/c3py00575e
44. Ogoshi, T.; Hasegawa, Y.; Aoki, T.; Ishimori, Y.; Inagi, S.; Yamagishi, T.-A. Reduction of Emeraldine Base Form of Polyaniline by Pillar[5]arene Based on Formation of Poly(pseudorotaxane) Structure Macromolecules 2011, 44, 7639-7644 10.1021/ma2016979
45. Liao, X.; Guo, L.; Chang, J.; Liu, S.; Xie, M.; Chen, G. Thermoresponsive AuNPs Stabilized by Pillararene-Containing Polymers Macromol. Rapid Commun. 2015, 36, 1492-1497 10.1002/marc.201500167
46. Laggoune, N.; Delattre, F.; Lyskawa, J.; Stoffelbach, F.; Guigner, J. M.; Ruellan, S.; Cooke, G.; Woisel, P. Synthesis, Binding and Self-assembly Properties of a Well-defined Pillar[5]arene End Functionalised Polydimethylacrylamide Polym. Chem. 2015, 6, 7389-7394 10.1039/C5PY01186H
47. Ogoshi, T.; Aoki, T.; Ueda, S.; Tamura, Y.; Yamagishi, T. Pillar[5]arene-Based Nonionic Polyrotaxanes and a Topological Gel Prepared from Cyclic Host Liquids Chem. Commun. 2014, 50, 6607-6609 10.1039/c4cc02833c
48. Song, N.; Chen, D.-X.; Qiu, Y.; Yang, X.; Xu, B.; Tian, W.; Yang, Y. Stimuli-Responsive Blue Fluorescent Supramolecular Polymers Based on a Pillar[5]arene Tetramer Chem. Commun. 2014, 50, 8231-8234 10.1039/c4cc03105a
49. Shi, B.; Xia, D.; Yao, Y. A Water-Soluble Supramolecular Polymer Constructed by Pillar[5]arene-Based Molecular Recognition Chem. Commun. 2014, 50, 13932-13935 10.1039/C4CC06971D
50. Bhowmik, P.; Han, H.; Nedeltchev, A. Synthesis and Characterization of Poly(pyridinium salts) with Organic Counterions Exhibiting both Thermotropic Liquid-Crystalline and Light-Emitting Properties J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1028-1041 10.1002/pola.21181
51. Soares, B. G.; Livi, S.; Duchet-Rumeau, J.; Gerard, J. Preparation of Epoxy/MCDEA Networks Modified with Ionic Liquids Polymer 2012, 53, 60-66 10.1016/j.polymer.2011.11.043
52. Wang, D.; Wang, M.; Wang, X.; Zhang, R.; Ma, J.; Sun, L. Influence of the Built-in Pyridinium Salt on Asymmetric Epoxidation of Substituted Chromenes Catalysed by Chiral (Pyrrolidine Salen) Mn(III) Complexes J. Mol. Catal. A: Chem. 2007, 270, 278-283 10.1016/j.molcata.2007.01.052
53. Thordarson, P. Determining Association Constants from Titration Experiments in Supramolecular Chemistry Chem. Soc. Rev. 2011, 40, 1305-1323 10.1039/C0CS00062K
54. Ogoshi, T.; Aoki, T.; Shiga, R.; Iizuka, R.; Ueda, S.; Demachi, K.; Yamafuji, D.; Kayama, H.; Yamagishi, T. Cyclic Host Liquids for Facile and High-Yield Synthesis of [2]Rotaxanes J. Am. Chem. Soc. 2012, 134, 20322-20325 10.1021/ja310757p
55. Du, P.; Chen, G. S.; Jiang, M. Electrochemically Sensitive Supra-crosslink and Its Corresponding Hydrogel Sci. China: Chem. 2012, 55, 836-843 10.1007/s11426-012-4515-z
56. Araki, J.; Ito, K. Recent Advances in the Preparation of Cyclodextrin-based Polyrotaxanes and Their Applications to Soft Materials Soft Matter 2007, 3, 1456-1473 10.1039/b705688e
57. Li, J. Cyclodextrin Inclusion Polymers Forming Hydrogels Adv. Polym. Sci. 2009, 222, 175-203 10.1007/12_2008_9
58. Li, C. Pillararene-based supramolecular polymers: from molecular recognition to polymeric aggregates Chem. Commun. 2014, 50, 12420-12433 10.1039/C4CC03170A
59. Hoffart, D. J.; Tiburcio, J.; de la Torre, A.; Knight, L. K.; Loeb, S. J. Cooperative Ion-ion Interactions in the Formation of Interpenetrated Molecules Angew. Chem., Int. Ed. 2008, 47, 97-101 10.1002/anie.200703019
60. Taura, D.; Taniguchi, Y.; Hashidzume, A.; Harada, A. Macromolecular Recognition of Cyclodextrin: Inversion of Selectivity of beta-Cyclodextrin toward Adamantyl Groups Induced by Macromolecular Chains Macromol. Rapid Commun. 2009, 30, 1741-1744 10.1002/marc.200900283
61. Li, Z. Y.; Zhang, Y. Y.; Zhang, C. W.; Chen, L. J.; Wang, C.; Tan, H. W.; Yu, Y. H.; Li, X. P.; Yang, H. B. Cross-Linked Supramolecular Polymer Gels Constructed from Discrete Multi-pillar[5]arene Metallacycles and Their Multiple Stimuli-Responsive Behavior J. Am. Chem. Soc. 2014, 136, 8577-8589 10.1021/ja413047r
62. Liao, X.; Chen, G.; Jiang, M. Pseudopolyrotaxanes on Inorganic Nanoplatelets and Their Supramolecular Hydrogels Langmuir 2011, 27, 12650-12656 10.1021/la202555t
63. Li, J.; Li, X.; Zhou, Z.; Ni, X.; Leong, K. W. Formation of Supramolecular Hydrogels Induced by Inclusion Complexation between Pluronics and alpha-Cyclodextrin Macromolecules 2001, 34, 7236-7237 10.1021/ma010742s