Self-assembly of two-component gels: Stoichiometric control and component selection

Chemistry - A European Journal

Volumn 15, Issue 2, 2009, Pages 372-379

  Hirst, Andrew R ^a   Miravet, Juan F ^b   Escuder, Beatriu ^b   Noirez, Laurence ^c   Castelletto, Valeria ^d   Hamley, Ian W ^d   Smith, David K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b UNIVERSITAT JAUME I   (Spain)

^c CEA SACLAY   (France)

^d UNIVERSITY OF READING   (United Kingdom)

Author keywords

Dendrimers; Gels; Self assembly; Soft materials

Indexed keywords

AMINES; AMINO ACIDS; CIRCULAR DICHROISM SPECTROSCOPY; COMPETITION; CONTROL SYSTEMS; DENDRIMERS; DICHROISM; GELATION; HIERARCHICAL SYSTEMS; NEUTRON SCATTERING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SELF ASSEMBLY;

AROMATIC DIAMINES; CIRCULAR DICHROISM (DC); COMPONENT ASSEMBLIES; COMPONENT SELECTION (CS); GEL NETWORKS; GEL SYSTEMS; L-LYSINE (PLL); MOLAR RATIOS; NANO STRUCTURING; NMR RELAXATION; NMR SPECTROS COPY; PHASE MATERIALS; SELF-ASSEMBLING; SMALL ANGLE NEUTRON SCATTERING (SANS); SOFT MATERIALS; TERNARY COMPLEXES; TUN ABILITY; TWO-COMPONENT SYSTEMS;

GELS;

ANTHRACENE DERIVATIVE; DENDRON; DIAMINE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; DRUG MIXTURE; ENZYME SPECIFICITY; GEL; NEUTRON DIFFRACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SMALL ANGLE SCATTERING; TRANSITION TEMPERATURE;

ANTHRACENES; CIRCULAR DICHROISM; COMPLEX MIXTURES; DIAMINES; GELS; MAGNETIC RESONANCE SPECTROSCOPY; NEUTRON DIFFRACTION; SCATTERING, SMALL ANGLE; SUBSTRATE SPECIFICITY; TRANSITION TEMPERATURE;

EID: 58449090035     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801475     Document Type: Article

References (93)

1. Organic Nanostructures (Eds.: J. L. Atwood, J. W. Steed), Wiley-VCH, Weinheim, 2008.
2. a) A. R. Hirst, B. Escuder, J.-F. Miravet, D. K. Smith, Angew. Chem. 2008, 120, 8122-8139;
3. Angew. Chem. Int. Ed. 2008, 47, 8002-8018;
4. b) N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821-836.
5. a) Molecular Gels; Materials with Self-Assembled Fibrillar Networks (Eds.: R. G. Weiss, P. Terech), Springer, Dordrecht, 2006;
6. b) D. K. Smith, Molecular Gels-Nanostructured Soft Materials in Organic Nanostructures (Eds.: J. L. Atwood, J. W. Steed), Wiley-VCH, Weinheim, 2008.
7. For a review of two-component gels see: A. R. Hirst, D. K. Smith, Chem. Eur. J. 2005, 11, 5496-5508.
8. For selected examples of two-component gels based on hydrogen bonding and acid-amine interactions: a) K. Hanabusa, T. Miki, Y. Taguchi, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1993, 1382-1384;
9. b) K. Inoue, Y. Ono, Y. Kanekiyo, T. Ishi-i, K. Yoshihara, S. Shinkai, J. Org. Chem. 1999, 64, 2933-2937;
10. c) X. Xu, M. Ayyagari, M. Tata, V. T. John, G. L. McPherson, J. Phys. Chem. 1993, 97, 11350-11353;
11. d) M. Tata, V. T. John, Y.Y Waguespack, G. L. McPherson, J. Am. Chem. Soc. 1994, 116, 9464-9470;
12. e) B. A. Simmons, C. E. Taylor, F. A. Landis, V. T. John, G. L. McPherson, D. K. Schwartz, R. Moore, J. Am. Chem. Soc. 2001, 123, 2414-2421;
13. f) H. M. Willemen, T. Vermonden, A. T. M. Marcelis, E. J. R. Sudhölter, Langmuir 2002, 18, 7102-7106;
14. g) M. de Loos, J. van Esch, R. M. Kellogg, B. L. Feringa, Angew. Chem. 2001, 113, 633-636;
15. Angew. Chem. Int. Ed. 2001, 40, 613-616;
16. h) K. Nakano, Y. Hishikawa, K. Sada, M. Miyata, K. Hanabusa, Chem. Lett. 2000, 1170-1171;
17. i) G. M. Dykes, D. K. Smith, Tetrahedron 2003, 59, 3999-4009;
18. j) J. G. Hardy, A. R. Hirst, D. K. Smith, C. Brennan, I. Ashworth, Chem. Commun. 2005, 385-387;
19. k) M. Suzuki, H. Saito, H. Shirai, K. Hanabusa, New J. Chem. 2007, 31, 1654-1660.
20. For selected examples of two-component gels based on donor-acceptor interactions: a) U. Maitra, P. V. Kumar, N. Chandra, L. J. D'Sousa, M. D. Prasanna, A. R. Raju, Chem. Commun. 1999, 595-596;
21. b) A. Friggeri, O. Gronwald, K. J. C. van Bommel, S. Shinkai, D. N. Reinhoudt, J. Am. Chem. Soc. 2002, 124, 10754-10758;
22. c) P. Babu, N. M. Sangeetha, P. Vijaykumar, U. Maitra, K. Rissanen, A. R. Raju, Chem. Eur. J. 2003, 9, 1922-1932;
23. d) B. G. Bag, G. C. Maity, S. K. Dinda, Org. Lett. 2006, 8, 5457-5460;
24. e) J. R. Moffat, D. K. Smith, Chem. Commun. 2008, 2248-2250.
25. For selected examples of two-component gels based on ligand-metal interactions: a) M. Enomoto, A. Kishimura, T. Aida, J. Am. Chem. Soc. 2001, 123, 5608-5609;
26. b) A. Kishimura, T. Yamashita, T. Aida, J. Am. Chem. Soc. 2005, 127, 179-183;
27. c) A. Ghoussoub, J.-M. Lehn, Chem. Commun. 2005, 5763-5765;
28. d) M. Shirakawa, N. Fujita, T. Tani, K. Kaneko, S. Shinkai, Chem. Commun. 2005, 4149-4151;
29. e) S. Kume, K. Kuroiwa, N. Kimizuka, Chem. Commun. 2006, 2442-2444;
30. f) A. Y.-Y. Tam, K. M.-C. Wong, G. Wang, V. W.-W. Yam, Chem. Commun. 2007, 2028-2030;
31. g) U. Hahn, A. R. Hirst, J. L. Delgado, A. Kaeser, B. Delavaux-Nicot, J.-F. Nierengarten, D. K. Smith, Chem. Commun. 2007, 4943-4945.
32. For selected examples of two-component gels based on reversible chemical reactions: a) M. George, R. G. Weiss, Langmuir 2003, 19, 1017-1025;
33. b) M. George, R. G. Weiss, Langmuir 2002, 18, 7124-7135.
34. a) A. R. Hirst, D. K. Smith, M. C. Feiters, H. P. M. Geurts, A. C. Wright, J. Am. Chem. Soc. 2003, 125, 9010-9011;
35. b) A. R. Hirst, D. K. Smith, J. P. Harrington, Chem. Eur. J. 2005, 11, 6552-6559.
36. H. Y. Lee, S. R. Nam, J-I. Hong, J. Am. Chem. Soc. 2007, 129, 1040-1041.
37. P. Mukhopadhyay, Y. Iwashita, M. Shirakawa, S.-I. Kawano, N. Fujita, S. Shinkai, Angew. Chem. 2006, 118, 1622-1625;
38. Angew. Chem. Int. Ed. 2006, 45, 1592-1595.
39. C. E. Stanley, N. Clarke, K. M. Anderson, J. A. Elder, J. T. Lenthall, J. W. Steed, Chem. Commun. 2006, 3199-3201.
40. S. J. Brignell, D. K. Smith, New J. Chem. 2007, 31, 1243-1249.
41. For selected examples see: a) K. J. C. van Bommel, C. van der Pol, I. Muizebelt, A. Friggeri, A. Heeres, A. Meetsma, B. L. Feringa, J. van Esch, Angew. Chem. 2004, 116, 1695-1699;
42. Angew. Chem. Int. Ed. 2004, 43, 1663-1667;
43. b) Y. Zhang, H. Gu, Z. Yang, B. Xu, J. Am. Chem. Soc. 2003, 125, 13680-13681;
44. c) J. E. A. Webb, M. J. Crossley, P. Turner, P. Thordarson, J. Am. Chem. Soc. 2007, 129, 7155-7162;
45. d) Z. Dzolic, M. Cametti, A. D. Cort, L. Mandolini, M. Zinic, Chem. Commun. 2007, 3535-3537;
46. e) W. Deng, H. Yamaguchi, Y. Takshima, A. Harad, Angew. Chem. 2007, 119, 5236-5239;
47. Angew. Chem. Int. Ed. 2007, 46, 5144-5147;
48. f) M. Yamanaka, T. Nakamura, T. Nakagawa, H. Itagaki, Tetrahedron Lett. 2007, 48, 8990-8993.
49. D. K. Smith, Chem. Commun. 2006, 34-44.
50. A. R. Hirst, D. K. Smith, M. C. Feiters, H. P. M. Geurts, Langmuir 2004, 20, 7070-7077.
51. A. R. Hirst, D. K. Smith, Org. Biomol. Chem. 2004, 2, 2965-2971.
52. A. R. Hirst, D. K. Smith, Langmuir 2004, 20, 10851-10857.
53. A. R. Hirst, D. K. Smith, M. C. Feiters, H. P. M. Geurts, Chem. Eur. J. 2004, 10, 5901-5910.
54. J. G. Hardy, A. R. Hirst, I. Ashworth, C. Brennan, D. K. Smith, Tetrahedron 2007, 63, 7397-7406.
55. A. R. Hirst, I. A. Coates, T. Boucheteau, B. Escuder, J.-F. Miravet, V. Castelletto, I. W. Hamley, D. K. Smith, J. Am. Chem. Soc. 2008, 130, 9113-9121.
56. For selected examples of self-sorting processes see: a) R. Kramer, J.-M. Lehn, A. Marquis-Rigault, Proc. Natl. Acad. Sci. USA 1993, 90, 5394-5398;
57. b) S. J. Rowan, D. G. Hamilton, P. A. Brady, J. K. M. Sanders, J. Am. Chem. Soc. 1997, 119, 2578-2579;
58. c) P. N. Taylor, H. L. Anderson, J. Am. Chem. Soc. 1999, 121, 11538-11545;
59. d) B. Bilgicer, X. Xing, K. Kumar, J. Am. Chem. Soc. 2001, 123, 11815-11816;
60. e) I. W. Hwang, T. Kamada, T. K. Ahn, D. M. Ko, T. Nakamura, A. Tsuda, A. Osuka, D. Kim, J. Am. Chem. Soc. 2004, 126, 16187-16198;
61. f) S. G. Telfer, T. Sato, R. Kuroda, J. LeFebvre, D. B. Leznoff, Inorg. Chem. 2004, 43, 421-429;
62. g) A. X. Wu, L. Isaacs, J. Am. Chem. Soc. 2003, 125, 4831-4835;
63. h) P. Mukhopadhyay, A. Wu, L. Isaacs, J. Org. Chem. 2004, 69, 6157-6164;
64. i) N. A. Schnarr, A. J. Kennan, J. Am. Chem. Soc. 2003, 125, 667-671;
65. j) N. Sreenivasachary, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 2005, 102, 5938-5943;
66. k) S. M. Liu, C. Ruspic, P. Mukhopadhyay, S. Chakrabarti, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2005, 127, 15959-15967;
67. l) I. Saur, R. Scopelliti, K. Severin, Chem. Eur. J. 2006, 12, 1058-1066;
68. m) C. Burd, M. Weck, Macromolecules 2005, 38, 7225-7230;
69. n) P. Mukhopadhyay, P. Y. Zavalij, L. Isaacs, J. Am. Chem. Soc. 2006, 128, 14093-14102;
70. o) N. Severin, I. M. Sokolov, N. Miyashita, D. G. Kurth, J. P. Rabe, Macromolecules 2007, 40, 5182-5186;
71. p) M. K. Khan, P. R. Sundararaian, J. Phys. Chem. B 2008, 112, 4223-4232;
72. q) D. Braekers, C. Peters, A. Bogdan, Y. Rudzevich, V. Böhmer, J. F. Desreux, J. Org. Chem. 2008, 73, 701-706.
73. a) A. R. Hirst, B. Huang, V. Castelletto, I. W. Hamley, D. K. Smith, Chem. Eur. J. 2007, 13, 2180-2188;
74. b) J. R. Moffat, D. K. Smith, Chem. Commun. 2008, DOI: 10.1039/b818058j.
75. a) G. M. Dykes, L. J. Brierley, D. K. Smith, P. T. McGrail, G. J. Seeley, Chem. Eur. J. 2001, 7, 4730-4739;
76. b) M. Driffield, D. M. Goodall, D. K. Smith, Org. Biomol. Chem. 2003, 1, 2612-2620;
77. c) G. M. Dykes, D. K. Smith, A. Caragheorgheopol, Org. Biomol. Chem. 2004, 2, 922-926.
78. H. C. Brown, D. H. McDaniel, O. Häflinger in Determination of Organic Structures by Physical Methods (Eds.: E. A. Braude, F. C. Nachod), Academic Press, New York, 1955.
79. S. R. Raghavan, B. H. Cipriano, Gel Formation: Phase Diagrams using Tabletop Rheology and Calorimetry in Molecular Gels, Materials with Self-Assembled Fibrillar Networks (Eds.: R. G. Weiss, P. Terech), Springer, Dordrecht, 2006, chap. 8.
80. Y. Y. Waguespack, S. Banerjee, P. Ramannair, G. C. Irvin, V. T. John, G. L. McPherson, Langmuir 2000, 16, 3036-3041.
81. B. Escuder, M. Llusar, J.-F. Miravet, J. Org. Chem. 2006, 71, 7747-7752.
82. For an overview of CD spectroscopy see: N. Berova, K. Nakanishi, R. W. Woody, Circular Dichroism: Principles and Applications, 2nd ed., Wiley-VCH, Weinheim, 1994.
83. For a review see: a) S. Allenmark, Chirality 2003, 15, 409-422;
84. For selected examples see: b) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788;
85. c) C. Thalacker, F. Würthner, Adv. Funct. Mater. 2002, 12, 209-218;
86. d) T. Miyagawa, M. Yamamoto, R. Muraki, H. Onouchi, E. Yashima, J. Am. Chem. Soc. 2007, 129, 3676-3682;
87. e) Y. Li, T. Wang, M. Liu, Soft Matter 2007, 3, 1312-1317.
88. O. Glatter, O. Kratky, Small Angle X-ray Scattering, Academic Press, London 1982.
89. R. F. Ludlow, S. Otto, Chem. Soc. Rev. 2008, 37, 101-108.
90. D. C. Duncan, D. G. Whitten, Langmuir 2000, 16, 6445-6452.
91. X. Salvatella, E. Giralt, Chem. Soc. Rev. 2003, 32, 365-372.
92. a) I. Yoshimura, Y. Miyahara, N. Kasagi, H. Yamane, A. Ojida, I. Hamachi, J. Am. Chem. Soc. 2004, 126, 12204-12205;
93. b) S. Yamaguchi, I. Yoshimura, T. Kohira, S.-i. Tamaru, I. Hamachi, J. Am. Chem. Soc. 2005, 127, 11835-11841.