Pro-ionomers: An anion metathesis approach to amphiphilic block lonomers from neutral precursors

Advanced Materials

Volumn 20, Issue 16, 2008, Pages 3096-3099

  Tang, Tingji ^a   Coady, Daniel J ^a   Boydston, Andrew J ^a   Dykhno, Olga L ^a   Bielawski, Christopher W ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABS RESINS; AGGLOMERATION; BLOCK COPOLYMERS; COLLOIDS; COPOLYMERIZATION; COPOLYMERS; EMISSION SPECTROSCOPY; IONOMERS; MICELLES; NANOSTRUCTURED MATERIALS; PLASTIC PRODUCTS; SHELLS (STRUCTURES);

ALKYL SULFONATES; AMPHIPHILIC; ANION METATHESES; BLOCK IONOMERS; CONSISTENT; CROSSLINKED MICELLES; EXCIMERS; IMIDAZOLIUM; NANOMATERIALS; NUCLEOPHILICITIES; PHOTOPHYSICAL; SELF-ASSEMBLY; STEP METHODS; TECHNICAL DIFFICULTIES;

POLYMERS;

EID: 54949084638     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/adma.200800291     Document Type: Article

References (39)

1. a) Y. Ishihara, H. S. Bazzi, V. Toader, F. Goden, H. F. Sleiman, Chem. Eur. J. 2007, 13, 4560.
2. b) D. E. Discher, V. Ortiz, G. Srinivas, M. L. Kleim, Y. Kim, D. Christian, S. Cai, P. Photos, F. Ahmed, Prog. Polym. Sci. 2007, 32, 838.
3. c) A. B. Lowe, M. Torres, R. Wang, J. Polym. Sci. Part A 2 2007, 45, 5864.
4. d) J. Li, W.-D. He, X.-L. Sun, J. Polym. Sci. Part A 2007, 45, 5156.
5. e) R. K. O'Reilly, M. J. Joralemon, C. J. Hawker, K. L. Wooley, J. Polym. Sci. Part A 2007, 44, 5203.
6. f) Y. Chen, A. E. Tavakley, T. M. Mathiason, T. A. Taton, J. Polym. Sci. Part A 2007, 44, 2604.
7. g) A. Klaikherd, B. S. Sandanaraj, D. R. Vutukuri, S. Thayumanavan, J. Am. Chem. Soc. 2006, 128, 9231.
8. h) R. K. O'Reilly, C. J. Hawker, K. L. Wooley, Chem. Soc. Rev. 2006, 35, 1068.
9. i) L. You, H. Schlaad, J. Am. Chem. Soc. 2006, 128, 13336.
10. j) M. Licciardi, Y. Tang, N. C. Billingham, S. P. Armes, Biomacromolecules 2005, 6, 1085.
11. k) T. K. Bronich, P. A. Keifer, L. S. Shlyakhtenko, A. V. Kabanov, J. Am. Chem. Soc. 2005, 127, 8236.
12. l) J. Rodriguez-Hernàndez, S. Lecommandoux, J. Am. Chem. Soc. 2005, 127, 2026.
13. m) S. Radoslav, L. Laibin, A. Eisenberg, M. Dusica, Science 2003, 300, 615.
14. n) J. P. Kennedy, G. Fenyvesi, R. P. Levy, K. S. Rosenthal, Macromol. Symp. 2001, 772, 56.
15. a) D. J. Pochan, Z. Chen, H. Cui, K. Hales, K. Qi, K. L. Wooley, Science 2004, 306, 94.
16. b) L. Zhang, A. Eisenberg, Science 1995, 268, 1728.
17. a) H. Cui, Z. Chen, S. Zhong, K. L. Wooley, D. J. Pochan, Science 2007, 317, 647.
18. b) H. Cui, Z. Chen, K. L. Wooley, D. J. Pochan, Macromolecules 2006, 39. 6599.
19. c) J. Du, Y. Tang, A. L. Lewis, S. P. Armes, J. Am. Chem. Soc. 2005, 127, 17982.
20. d) L. Zhang, A. Eisenberg, Science 1996, 272, 1777.
21. a) A. J. Boydston, P. D. Vu, O. L. Dykhno, V. Chang, A. R. Wyatt, II, A. S. Stockett, E. T. Ritschdorff, J. B. Shear, C. W. Bielawski, J. Am. Chem. Soc. 2008, 130, 3143.
22. b) A. J. Boydston, C. S. Pecinovsky, S. T. Chao, C. W. Bielawski, J. Am. Chem. Soc. 2007, 129, 14550.
23. The methodology appears to be broadly applicable. For example, combination of 1-methyl-3-phenylbenzimidazolium iodide with proionomer 1 also afforded micelles (see Supporting Information).
24. This process is reminiscent of the Krapcho decarboxylation, see: A. P. Krapcho, O. A. Glynn, B. J. Orenon, Tetrahedron Lett. 1967, 8, 215.
25. For other reactions that capitalize on halide nucleophilicities, see: a) E. Kunst, F. Gallier, D. Dujardin, M. S. Yusubov, A. Kirschning, Org. Lett. 2007, 9, 5199.
26. b) P. D. Vu, A. J. Boydston, C. W. Bielawski, Green Chem. 2007, 9, 1158.
27. c) W. T. Ford, R. J. Hauri, S. G. Smith, J. Am. Chem. Soc. 1974, 96, 4316.
28. K. Matyjaszewski, J. Xia, Chem. Rev. 2001, 101, 2921.
29. See Supporting Information.
30. 3).
31. Investigations examining the relationship between molecular weight of the pro-ionomers and the structure of its respective micelles are underway and will be reported in due course.
32. Samples prepared under more dilute concentrations (ca. 0.1 wt %) afforded micelles with similar average diameters as those described above, although fewer micelles per unit area were observed, as expected. Furthemore, at lower concentrations, the TEM images of micelles formed from 5 appeared to have a lower occurance of clusters.
33. Graphic representations of idealized micelle structures are provided (see Supporting Information).
34. 4 and imaged as described above. These images showed only single stained regions, as opposed to bilayer formation which would be expected if their structures were vesicular (see Supporting Information).
35. Similar effects have been observed in other systems, see: a) M. Kumbhakar, R. Ganguly, J. Phys. Chem. B 2007, 111, 3995.
36. b) H. Huo, K. Li, Q. Wang, C. Wu, Macromolecules 2007, 40, 6692.
37. c) M. Mizusaki, N. Kopek, Y. Morishima, F. M. Winnik, Langmuir 1999, 15, 8090.
38. a) Y. Teng, M. E. Morrison, P. Munk, S. E. Webber, K. Prochazka, Macromolecules 1998, 31, 3578.
39. b) F. M. Winnik, Chem. Rev. 1993, 93, 587.