Fibrous networks with incorporated macrocycles: A chiral stimuli-responsive supramolecular supergelator and its application to biocatalysis in organic media

Chemistry - A European Journal

Volumn 19, Issue 31, 2013, Pages 10150-10159

  Qi, Zhenhui ^a   Wu, Changzhu ^a   Malo De Molina, Paula ^b   Sun, Han ^c   Schulz, Andrea ^a   Griesinger, Christian ^c   Gradzielski, Michael ^b   Haag, Rainer ^a   Ansorge Schumacher, Marion B ^b,d   Schalley, Christoph A ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^c MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

^d DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

biocatalysis; crown compounds; gels; host guest systems; self assembly

Indexed keywords

BIOCATALYSIS; CROWN COMPOUNDS; HOST GUEST INTERACTIONS; HOST-GUEST SYSTEM; LOW MOLECULAR WEIGHT; SOL-GEL PHASE TRANSITION; STEREOGENIC CENTERS; SUPRAMOLECULAR GELS;

CROWN ETHERS; ENZYME IMMOBILIZATION; FIBER OPTIC CHEMICAL SENSORS; GELATION; GELS; LIGANDS; METABOLISM; ORGANIC SOLVENTS; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY; UREA;

PHASE INTERFACES;

CROWN COMPOUND; CROWN ETHER; DRUG DERIVATIVE; MACROCYCLIC COMPOUND; SOLVENT; UREA;

ARTICLE; BIOCATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; GEL; HOST-GUEST SYSTEMS; INFRARED SPECTROSCOPY; SELF-ASSEMBLY; STEREOISOMERISM; SYNTHESIS;

BIOCATALYSIS; CROWN COMPOUNDS; GELS; HOST-GUEST SYSTEMS; SELF-ASSEMBLY;

BIOCATALYSIS; CROWN ETHERS; GELS; MACROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; UREA;

EID: 84881383991     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300193     Document Type: Article

References (100)

1. D. A. Fletcher, R. D. Mullins, Nature 2010, 463, 485-492.
2. S.-i. Tamaru, M. Ikeda, Y. Shimidzu, S. Matsumoto, S. Takeuchi, I. Hamachi, Nat. Commun. 2010, 1, 20.
3. N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836
4. R. G. Weiss, Acc. Chem. Res. 2006, 39, 489-497
5. P. Dastidar, Chem. Soc. Rev. 2008, 37, 2699-2715
6. L. E. Buerkle, S. J. Rowan, Chem. Soc. Rev. 2012, 41, 6089-6102
7. A. Noro, M. Hayashi, Y. Matsushita, Soft Matter 2012, 8, 2416-2429
8. D. K. Smith, in Supramolecular Chemistry: From Molecules to Nanomaterials (Eds.:, P. A. Gale, J. W. Steed,), Wiley, Hoboken, 2012, pp. 3355-3376
9. H. Svobodová, V. Noponen, E. Kolehmainen, E. Sievanen, RSC Adv. 2012, 2, 4985-5007
10. S. Seiffert, J. Sprakel, Chem. Soc. Rev. 2012, 41, 909-930
11. D. Das, T. Kar, P. K. Das, Soft Matter 2012, 8, 2348-2365
12. E. A. Appel, J. del Barrio, X. J. Loh, O. A. Scherman, Chem. Soc. Rev. 2012, 41, 6195-6214.
13. T. Ogoshi, Y. Takashima, H. Yamaguchi, A. Harada, J. Am. Chem. Soc. 2007, 129, 4878-4879
14. H. Maeda, Chem. Eur. J. 2008, 14, 11274-11282
15. G. O. Lloyd, J. W. Steed, Nat. Chem. 2009, 1, 437-442
16. J. H. Kim, M. Seo, Y. J. Kim, S. Y. Kim, Langmuir 2009, 25, 1761-1766
17. T. Tazawa, S. Yagai, Y. Kikkawa, T. Karatsu, A. Kitamura, A. Ajayaghosh, Chem. Commun. 2010, 46, 1076-1078
18. J. A. Foster, J. W. Steed, Angew. Chem. 2010, 122, 6868-6874
19. Angew. Chem. Int. Ed. 2010, 49, 6718-6724
20. Y. Suzaki, T. Taira, K. Osakada, J. Mater. Chem. 2011, 21, 930-938
21. D. Díaz Díaz, D. Kühbeck, R. J. Koopmans, Chem. Soc. Rev. 2011, 40, 427-448
22. Y.-S. Su, J.-W. Liu, Y. Jiang, C.-F. Chen, Chem. Eur. J. 2011, 17, 2435-2441
23. X. Wang, L. Zhou, H. Wang, Q. Luo, J. Xu, J. Liu, J. Colloid Interface Sci. 2011, 353, 412-419
24. F. Rodríguez-Llansola, J. F. Miravet, B. Escuder, Chem. Commun. 2011, 47, 4706-4708
25. V. Lozano, R. Hernandez, A. Arda, J. Jimenez-Barbero, C. Mijangos, M.-J. Perez-Perez, J. Mater. Chem. 2011, 21, 8862-8870
26. L. Chen, Y.-K. Tian, Y. Ding, Y.-J. Tian, F. Wang, Macromolecules 2012, 45, 8412-8419
27. L. Tan, Y. Liu, W. Ha, L.-S. Ding, S.-L. Peng, S. Zhang, B.-J. Li, Soft Matter 2012, 8, 5746-5749.
28. X. Liao, X. Chen, G. Chen, X, Liu, W. Chen, F. Chen, M. Jiang, Angew. Chem. 2010, 122, 4511-4515
29. Angew. Chem. Int. Ed. 2010, 49, 4409-4413
30. A. Harada, R. Kobayashi, Y. Takashima, A. Hashidzume, H, Yamaguchi, Nat. Chem. 2011, 3, 34-37
31. S. Tamesue, Y. Takashima, H. Yamaguchi, S. Shinkai, A. Harada, Angew. Chem. 2010, 122, 7623-7626
32. Angew. Chem. Int. Ed. 2010, 49, 7461-7464
33. S. Dong, Y. Luo, X. Yan, B. Zheng, X. Ding, Y. Yu, Z. Ma, Q. Zhao, F. Huang, Angew. Chem. 2011, 123, 1945-1949
34. Angew. Chem. Int. Ed. 2011, 50, 1905-1909
35. T. Akutagawa, K. Kakiuchi, T. Hasegawa, S. Noro, T. Nakamura, H. Hasegawa, S. Mashiko, J. Becher, Angew. Chem. 2005, 117, 7449-7453
36. Angew. Chem. Int. Ed. 2005, 44, 7283-7287
37. A. A. Sobczuk, S. Tamaru, S. Shinkai, Chem. Commun. 2011, 47, 3093-3095
38. I. Hwang, W. S. Jeon, H. J. Kim, D. Kim, H. Kim, N. Selvapalam, N. Fujita, S. Shinkai, K. Kim, Angew. Chem. 2007, 119, 214-217
39. Angew. Chem. Int. Ed. 2007, 46, 210-213
40. T. Becker, C. Y. Goh, F. Jones, M. J. McIldowie, M. Mocerino, M. I. Ogden, Chem. Commun. 2008, 3900-3902
41. X. Cai, K. Liu, J. Yan, H. Zhang, X. Hou, Z. Liu, Y. Fang, Soft Matter 2012, 8, 3756-3761
42. J. Liu, P. He, J. Yan, X. Fang, J. Peng, K. Liu, Y. Fang, Adv. Mater. 2008, 20, 2508-2511
43. X. Yan, D. Xu, X. Chi, J. Chen, S. Dong, X. Ding, Y. Yu, F. Huang, Adv. Mater. 2012, 24, 362-369.
44. J. H. Jung, H. Kobayashi, M. Masuda, T. Shimizu, S. Shinkai, J. Am. Chem. Soc. 2001, 123, 8785-8789
45. H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788.
46. G. M. Whitesides, B. Grzybowski, Science 2002, 295, 2418-2421
47. X. Yang, G. Zhang, D. Zhang, J. Mater. Chem. 2011, 21, 38-50
48. Z.-X. Liu, Y. Feng, Z.-C. Yan, Y.-M. He, C.-Y. Liu, Q.-H. Fan, Chem. Mater. 2012, 24, 3751-3757
49. M. D. Segarra-Maset, V. J. Nebot, J. F. Miravet, B. Escuder, Chem. Soc. Rev. 2013, DOI:.
50. A. R. Hirst, B. Escuder, J. F. Miravet, D. K. Smith, Angew. Chem. 2008, 120, 8122-8139
51. Angew. Chem. Int. Ed. 2008, 47, 8002-8018.
52. H. Komatsu, S. Matsumoto, S.-i. Tamaru, K. Kaneko, M. Ikeda, I. Hamachi, J. Am. Chem. Soc. 2009, 131, 5580-5585
53. Z. Qi, P. Malo de Molina, W. Jiang, Q. Wang, K. Nowosinski, A. Schulz, M. Gradzielski, C. A. Schalley, Chem. Sci. 2012, 3, 2073-2082.
54. Y. Gao, F. Zhao, Q. Wang, Y. Zhang, B. Xu, Chem. Soc. Rev. 2010, 39, 3425-3433
55. A. E. David, A. J. Yang, N. S. Wang, Methods Mol. Biol. 2011, 679, 49-66.
56. S. U. Pickering, J. Chem. Soc. 1907, 91, 2001-2021.
57. C. Wu, S. Bai, M. B. Ansorge-Schumacher, D. Wang, Adv. Mater. 2011, 23, 5694-5699
58. Z. Wang, M. C. M. van Oers, F. P. J. T. Rutjes, J. C. M. van Hest, Angew. Chem. 2012, 124, 10904-10908
59. Angew. Chem. Int. Ed. 2012, 51, 10746-10750.
60. J. H. van Esch, S. De Feyter, R. M. Kellogg, F. De Schryver, B. L. Feringa, Chem. Eur. J. 1997, 3, 1238-1243
61. J. H. van Esch, F. Schoonbeek, M. de Loos, H. Kooijman, A. L. Spek, R. M. Kellogg, B. L. Feringa, Chem. Eur. J. 1999, 5, 937-950
62. F. S. Schoonbeek, J. H. van Esch, R. Hulst, R. M. Kellogg, B. L. Feringa, Chem. Eur. J. 2000, 6, 2633-2643
63. A. Arnaud, L. Bouteiller, Langmuir 2004, 20, 6858-6863
64. Y. Jeong, K. Hanabusa, H. Masunaga, I. Akiba, K. Miyoshi, S. Sakurai, K. Sakurai, Langmuir 2005, 21, 586-594
65. L. Bouteiller, O. Colombani, F. Lortie, P. Terech, J. Am. Chem. Soc. 2005, 127, 8893-8898
66. C. Wang, D. Zhang, D. Zhu, Langmuir 2007, 23, 1478-1482
67. M. Bellot, L. Bouteiller, Langmuir 2008, 24, 14176-14182.
68. G. W. Gokel, W. M. Leevy, M. E. Weber, Chem. Rev. 2004, 104, 2723-2750
69. F. Huang, H. W. Gibson, Prog. Polym. Sci. 2005, 30, 982-1018
70. W. Jiang, C. A. Schalley, Beilstein J. Org. Chem. 2010, 6, 14.
71. C. Zhang, S. Li, J. Zhang, K. Zhu, N. Li, F. Huang, Org. Lett. 2007, 9, 5553-5556
72. C. Zhang, K. Zhu, S. Li, J. Zhang, F. Wang, M. Liu, N. Li, F. Huang, Tetrahedron Lett. 2008, 49, 6917-6920
73. W. Jiang, A. Schäfer, P. C. Mohr, C. A. Schalley, J. Am. Chem. Soc. 2010, 132, 2309-2320
74. X. Yan, M. Zhou, J. Chen, X. Chi, S. Dong, M. Zhang, X. Ding, Y. Yu, S. Shao, F. Huang, Chem. Commun. 2011, 47, 7086-7088
75. W. Jiang, D. Sattler, K. Rissanen, C. A. Schalley, Org. Lett. 2011, 13, 4502-4505.
76. J. W. Steed, Chem. Soc. Rev. 2010, 39, 3686-3699.
77. R. M. Versteegen, R. P. Sijbesma, E. W. Meijer, Macromolecules 2005, 38, 3176-3184.
78. M.-O. M. Piepenbrock, G. O. Lloyd, N. Clarke, J. W. Steed, Chem. Commun. 2008, 2644-2646.
79. A. Lohr, M. Lysetska, F. Würthner, Angew. Chem. 2005, 117, 5199-5202
80. Angew. Chem. Int. Ed. 2005, 44, 5071-5074.
81. P. Jonkheijm, P. van der Schoot, A. P. H. J. Schenning, E. W. Meijer, Science 2006, 313, 80-83.
82. W. Jiang, H. D. F. Winkler, C. A. Schalley, J. Am. Chem. Soc. 2008, 130, 13852-13853
83. W. Jiang, C. A. Schalley, Proc. Natl. Acad. Sci. USA 2009, 106, 10425-10429.
84. P. Terech, S. Friol, Tetrahedron 2007, 63, 7366-7374
85. P. Lo Nostro, R. Ramsch, E. Fratini, M. Lagi, F. Ridi, E. Carretti, M. Ambrosi, B. W. Ninham, P. Baglioni, J. Phys. Chem. B 2007, 111, 11714-11721
86. M. Burkhardt, S. Kinzel, M. Gradzielski, J. Colloid Interface Sci. 2009, 331, 514-521.
87. K. Martinek, A. Levashov, Y. Khmelnitsky, N. Klyachko, I. Berezin, Science 1982, 218, 889-891
88. C. Pizarro, M. A. Fernández-Torroba, C. Benito, J. M. González-Sáiz, Biotechnol. Bioeng. 1997, 53, 497-506
89. Q. Wang, Z. Yang, Y. Gao, W. Ge, L. Wang, B. Xu, Soft Matter 2008, 4, 550-553.
90. M. B. Ansorge-Schumacher, Immobilization of biological catalysts, Wiley-VCH, Weinheim, 2008
91. L. Cao, Carrier-bound Immobilized Enzymes: Principles, Applications and Design, Wiley-VCH, Weinheim, 2005
92. A. M. Klibanov, Science 1983, 219, 722-727
93. W. Tischer, F. Wedekind, Top. Curr. Chem. 1999, 200, 95-126.
94. M. B. Ansorge-Schumacher, Mini-Rev. Org. Chem. 2007, 4, 243-245
95. G. Carrea, S. Riva, Angew. Chem. 2000, 112, 2312-2341
96. Angew. Chem. Int. Ed. 2000, 39, 2226-2254
97. C. Wu, M. Kraume, M. B. Ansorge-Schumacher, ChemCatChem 2011, 3, 1314-1319
98. D. J. Cole-Hamilton, Science 2010, 327, 41-42.
99. P. Terech, C. Rossat, F. Volino, J. Colloid Interface Sci. 2000, 227, 363-370.
100. M. M. Bradford, Anal. Biochem. 1976, 72, 248-254.