Supramolecular aggregation of block copolymers in the solid state as assisted by the selective formation of inclusion crystals

Journal of the American Chemical Society

Volumn 133, Issue 23, 2011, Pages 8982-8994

  Bracco, Silvia ^a   Comotti, Angiolina ^a   Ferretti, Lisa ^a   Sozzani, Piero ^a  

^a UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; AMORPHOUS LAYER; COPOLYMER CHAINS; CRYSTALLINE LAMELLA; DRIVING FORCES; ETHYLENE OXIDES; GUEST-HOST INTERACTIONS; HOST GUEST INTERACTIONS; HOST MOLECULES; IN-SITU SYNCHROTRONS; INCLUSION COMPOUNDS; INTERMOLECULAR DISTANCE; INTERMOLECULAR INTERACTIONS; MAS NMR; MECHANOCHEMICALS; NANO CHANNELS; NON-COVALENT INTERACTION; NONCOVALENT; PHASE SEGREGATIONS; POLY(ETHYLENE OXIDE-B-PROPYLENE OXIDE-B-ETHYLENE OXIDE); SELECTIVE FORMATION; SELECTIVE INCLUSION; SOLVENT FREE; SPONTANEOUS FORMATION; STERIC EFFECT; SUPRAMOLECULAR AGGREGATION; SUPRAMOLECULAR ARCHITECTURES; SUPRAMOLECULAR SELF-ASSEMBLIES; THEORETICAL CALCULATIONS;

BLOCK COPOLYMERS; CALCULATIONS; COPOLYMERIZATION; CRYSTALLINE MATERIALS; CRYSTALS; DRUG INTERACTIONS; ETHYLENE; HYDRATES; MAGNETIC SUSCEPTIBILITY; NETWORK ARCHITECTURE; NUCLEAR MAGNETIC RESONANCE; PHASE SEPARATION; PROPYLENE; SUPRAMOLECULAR CHEMISTRY; X RAY DIFFRACTION;

PLASTIC PRODUCTS;

(TRIS O PHENYLENEDIOXYCYCLOTRIPHOSPHAZENE); COPOLYMER; ETHYLENE OXIDE; NANOCHANNEL; NANOCRYSTAL; POLY(ETHYLENE OXIDE BETA PROPYLENE OXIDE BETA ETHYLENE OXIDE); SOLVENT; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COVALENT BOND; CRYSTAL STRUCTURE; MECHANOTRANSDUCTION; MOLECULAR INTERACTION; NANOFABRICATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SUPRAMOLECULAR CHEMISTRY; SYNCHROTRON; THERMAL CONDUCTIVITY; X RAY DIFFRACTION;

EID: 79958857283     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201551n     Document Type: Article

References (90)

1. Lehn, J.-M. Science 2002, 295, 2400
2. Bates, F. S.; Fredrickson, G. H. Phys. Today 1999, 52, 32
3. Binder, K. Adv. Polym. Sci. 1994, 112, 181
4. Stupp, S. I. Curr. Opin. Colloid Interface Sci. 1998, 3, 20
5. Bates, F. S.; Fredrickson, G. H. Annu. Rev. Phys. Chem. 1990, 41, 525
6. Hamley, I. W. The Physics of Block Copolymers; Oxford University Press: Oxford, 1998.
7. Cornelissen, J. J. L. M.; Fischer, M.; Sommerijk, N. A. J. M.; Nolte, R. J. M. Science 1998, 280, 1427
8. Kang, Y.; Walish, J. J.; Gorishnyy, T.; Thomas, E. L. Nat. Mater. 2007, 6, 957
9. Jain, S.; Bates, F. S. Science 2003, 300, 460
10. Thurn-Albrecht, T.; Schotter, J.; Kastle, G. A.; Emley, N.; Shibauchi, T.; Krusin-Elbaum, L.; Guarini, K.; Black, C. T.; Tuominen, M. T.; Russell, T. P. Science 2000, 290, 2126
11. Jenekhe, S. A.; Chen, X. L. Science 1998, 279, 1903
12. Shefelbine, T. A.; Vigild, M. E.; Cussler, E. L.; Bates, F. S.; Matsen, M. W.; Hajduk, D. A.; Hillmyer, M. A. J. Am. Chem. Soc. 1999, 121, 8457
13. Lee, S.; Bluemle, M. J.; Bates, F. S. Science 2010, 330, 349
14. Zhao, D. Y.; Feng, J. L.; Huo, Q. S.; Melosh, N.; Fredrickson, G. H.; Chemlka, B. F.; Stucky, G. D. Science 1998, 279, 548
15. Warren, S. C.; Messina, L. C.; Slaughter, L. S.; Kamperman, M.; Zhou, Q.; Gruner, S. M.; DiSalvo, F. J.; Wiesner, U. Science 2008, 320, 1748
16. Tian, B.; Liu, X.; Solovyov, L. A.; Liu, Z.; Yang, H.; Zhang, Z.; Xie, S.; Zhang, F.; Tu, B.; Yu, C.; Terasaki, O.; Zhao, D. J. Am. Chem. Soc. 2004, 126, 865
17. Lee, M.; Park, M.-H.; Oh, N.-K.; Zin, W.-C.; Jung, H.-T.; Yoon, D. K. Angew. Chem., Int. Ed. 2004, 43, 6466
18. Pai, R. A.; Humayun, R.; Schulberg, M. T.; Sengupta, A.; Sun, J. N.; Watkins, J. J. Science 2004, 303, 507
19. Templin, M.; Franck, A.; DuChesne, A.; Leist, H.; Zhang, Y. M.; Ulrich, R.; Schadler, V.; Wiesner, U. Science 1997, 278, 1795
20. Zalusky, A. S.; Olayo-Valles, R.; Wolf, J. H.; Hillmyer, M. A. J. Am. Chem. Soc. 2002, 124, 12761
21. Koo, C. M.; Wu, L.; Lim, L. S.; Mahanthappa, M. K.; Hillmyer, M. A.; Bates, F. S. Macromolecules 2005, 38, 6090
22. Mao, H.; Hillmyer, M. A. Soft Matter 2006, 2, 57
23. Thomas, E. L.; Anderson, D. M.; Henkee, C. S.; Hoffman, D. Nature 1988, 334, 598
24. Ruokolainen, J.; Makinen, R.; Torkkeli, M.; Makela, T.; Serimaa, R.; Brinke, G. T.; Ikkala, O. Science 1998, 280, 557
25. Chen, Z.-R.; Kornfield, J. A.; Smith, S. D.; Grothaus, J. T.; Satkowski, M. M. Science 1997, 277, 1248
26. Lee, M.; Cho, B.-K.; Zin, W.-C. Chem. Rev. 2001, 101, 3869
27. Webster, O. W. Science 1991, 251, 887
28. Hadjichristidis, N.; Pitsikalis, M.; Pispas, S.; Iatrou, H. Chem. Rev. 2001, 101, 3747
29. Deming, T. J. Nature 1997, 390, 386
30. Balazs, A. C.; Emrick, T.; Russell, T. P. Science 2006, 314, 1107
31. Lin, Y.; Boker, A.; He, J.; Sill, K.; Xiang, H.; Abetz, C.; Li, X.; Wang, J.; Emrick, T.; Long, S.; Wang, Q.; Balazs, A. C.; Russell, T. P. Nature 2005, 434, 55
32. Hamley, I. W. Angew. Chem., Int. Ed. 2003, 42, 1692
33. Hajduk, D. A.; Harper, P. E.; Gruner, S. M.; Honeker, C. C.; Kim, G.; Thomas, E. L.; Fetters, L. J. Macromolecules 1994, 27, 4063
34. Valkama, S.; Kosonen, H.; Ruokolainen, J.; Haatainen, T.; Torkkeli, M.; Serimaa, R.; Ten Brinke, G.; Ikkala, O. Nat. Mater. 2004, 3, 872
35. Tirumala, V. R.; Romang, A.; Agarwal, S.; Lin, E. K.; Watkins, J. J. Adv. Mater. 2008, 20, 1603
36. Li, J.; Ni, X.; Zhou, Z.; Leong, K. W. J. Am. Chem. Soc. 2003, 125, 1788
37. Hsin-Fang Lee, H.-F.; Sheu, H.-S.; Jeng, U. S.; Huang, C. F.; Chang, F. C. Macromolecules 2005, 38, 6551
38. Miyata, M.; Tohnai, N.; Hisaki, I. Acc. Chem. Res. 2007, 40, 694
39. Miyata, M.; Sada, K. Comprehensive Supramolecular Chemistry, Solid-state Supramolecular Chemistry: Crystal Engineering; Pergamon: Oxford, 1996; Vol. 6, pp 147-176.
40. Toudic, B.; Garcia, P.; Odin, C.; Rabiller, P.; Ecolivet, C.; Collet, E.; Bourges, P.; McIntyre, G. J.; Hollingsworth, M.; Breczewski, T. Science 2008, 319, 5859
41. Harris, K. D. M. Chem. Soc. Rev. 1997, 26, 279
42. Farina, M.; Di Silvestro, G.; Sozzani, P. Comprehensive Supramolecular Chemistry, Solid-state Supramolecular Chemistry: Crystal Engineering; Pergamon: Oxford, UK, 1996; Vol. 6, pp 371-419.
43. Schilling, F. C.; Amundson, K. R.; Sozzani, P. Macromolecules 1994, 27, 6498
44. Sozzani, P.; Bovey, F. A.; Schilling, F. C. Macromolecules 1991, 24, 6764
45. Sozzani, P.; Bovey, F. A.; Schilling, F. C. Macromolecules 1989, 22, 4225
46. Sozzani, P.; Bracco, S.; Comotti, S.; Simonutti, R. Adv. Polym. Sci. 2005, 181, 153
47. Sozzani, P.; Comotti, A.; Bracco, S.; Simonutti, R. Chem. Commun. 2004, 768
48. Allcock, H. R.; Primrose, A. P.; Sunderland, N. J.; Rheingold, A. L.; Guzei, I. A.; Parvez, M. Chem. Mater. 1999, 11, 1243
49. Comotti, A.; Simonutti, R.; Catel, G.; Sozzani, P. Chem. Mater. 1999, 11, 1476
50. Sozzani, P.; Comotti, A.; Bracco, S.; Simonutti, R. Angew. Chem., Int. Ed. 2004, 43, 2811
51. Sozzani, P.; Bracco, S.; Comotti, A.; Ferretti, L.; Simonutti, R. Angew. Chem., Int. Ed. 2005, 44, 1816
52. Brustolon, M.; Barbon, A.; Bortolus, M.; Maniero, A. L.; Sozzani, P.; Comotti, A.; Simonutti, R. J. Am. Chem. Soc. 2004, 126, 15512
53. Bracco, S.; Comotti, A.; Beretta, M.; Valsesia, P.; Sozzani, P. Cryst. Eng. Commun. 2010, 12, 2318
54. Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025
55. Trask, A. V.; Jones, W. Top. Curr. Chem. 2005, 254, 41
56. Nguyen, K. L.; Friscic, T.; Day, G. M.; Gladden, L. F.; Jones., W. Nat. Mater. 2007, 6, 206
57. Shan, N.; Jones, W. Green Chem. 2003, 5, 728
58. Sokolov, A.; Swenson, D. C.; MacGillivray, L. R. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 1794
59. Etter, M. C.; Reutzel, S. M.; Choo, C. G. J. Am. Chem. Soc. 1993, 115, 4411
60. Sozzani, P.; Comotti, A.; Simonutti, R.; Meersmann, T.; Logan, J. W.; Pines, A. Angew. Chem., Int. Ed. 2000, 39, 2695
61. Meersmann, T.; Logan, J. W.; Simonutti, R.; Caldarelli, S.; Comotti, A.; Sozzani, P.; Kaiser, L. G.; Pines, A. J. Phys. Chem. A 2000, 104, 11665
62. Comotti, A.; Bracco, S.; Ferretti, L.; Mauri, M.; Simonutti, R.; Sozzani, P. Chem. Commun. 2007, 350
63. Comotti, A.; Simonutti, R.; Stramare, S.; Sozzani, P. Nanotechnology 1999, 10, 70
64. Allcock, H. R.; Levin, M. L.; Whittle, R. R. Inorg. Chem. 1986, 25, 41
65. For comparison purposes, powder X-ray diffraction patterns were collected as a function of temperature of the porous pure TPP hexagonal phase in the absence of the copolymer. At 373-423 K, the hexagonal phase of the empty TPP transforms into the more stable close-packed structure.
66. Bovey, F. A.; Mirau, P. NMR of Polymers; Academic Press: San Diego, CA, 1996.
67. van Rossum, B.-J.; de Groot, C. P.; Ladizhansky, V.; Vega, S.; de Groot, H. J. J. Am. Chem. Soc. 2000, 122, 3465
68. Sozzani, P.; Bracco, S.; Comotti, A.; Simonutti, R.; Camurati, I. J. Am. Chem. Soc. 2003, 125, 12881
69. Waugh, S.; Fessenden, R. W. J. Am. Chem. Soc. 1957, 79, 846
70. Johnson, C. E.; Bovey, F. A. J. Chem. Phys. 1958, 29, 1012
71. Von RaguéSchleyer, P.; Maerker, C.; Dransfeld, A.; Jiao, H.; Van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317
72. Canceill, J.; Lacombe, L.; Collet, A. J. Am. Chem. Soc. 1986, 108, 4230
73. Rapp, A.; Schnell, I.; Sebastiani, D.; Brown, S. P.; Percec, V.; Spiess, H. W. J. Am. Chem. Soc. 2003, 125, 13284
74. The linewidth of the crystalline phase component is attributed to motional broadening: Schantz, S. Macromolecules 1997, 30, 1419
75. 2 carbons do not experience any γ-gauche effect: Takahashi, Y.; Tadokoro, H. Macromolecules 1973, 6, 672
76. Tonelli, A. Macromolecules 1978, 11, 565
77. Farina, M.; Natta, G.; Allegra, G.; Loffelholz, M. J. Polym. Sci., Part C 1967, 16, 2517
78. Vinogradov, E.; Madhu, P. K.; Vega, S. Chem. Phys. Lett. 1999, 314, 443
79. Vega, S. Chem. Phys. Lett. 2007, 447, 370
80. Uemura, T.; Horike, S.; Kitagawa, K.; Mizuno, M.; Endo, K.; Bracco, S.; Comotti, A.; Sozzani, P.; Nagaoka, M.; Kitagawa, S. J. Am. Chem. Soc. 2008, 130, 6781
81. Sozzani, P.; Bracco, S.; Comotti, A.; Mauri, M.; Simonutti, R.; Valsesia, P. Chem. Commun. 2006, 1921
82. Comotti, A.; Bracco, S.; Sozzani, P.; Hawxwell, S. M.; Hu, C.; Ward, M. D. Cryst. Growth Des. 2009, 9, 3000
83. The low multiplicity of the TPP signals indicates the high symmetry of the TPP molecule in the hexagonal honeycomb structure in agreement with the X-ray diffraction structure.
84. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
85. The methane molecule was set with the C-H bond perpendicular to the aromatic plane in the shielding cone and at the magic angle, and parallel in the deshielding cone.
86. Takahashi, O.; Kohno, Y.; Nishio, M. Chem. Rev. 2010, 110, 6049
87. 3.
88. Meneghini, B.; Artioli, G.; Balerna, A.; Gualtieri, A. F.; Norby, P.; Mobilio, S. J. Synchrotron Radiat. 2001, 8, 1162
89. Larson, A. C.; Von Dreele, R. B. GSAS: Generalized Structure Analysis System Manual; Los Alamos National Laboratory Report LAUR-86-748; U.S. Government Printing Office: Washington, DC, 1994.
90. Von Dreele, R. B.; Jorgensen, J. D.; Windsor, C. G. J. Appl. Crystallogr. 1982, 15, 581