Charge-transfer reinforced folding of novel ionenes

Macromolecules

Volumn 42, Issue 22, 2009, Pages 8599-8603

  De, Swati ^a   Ramakrishnan, S ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER INTERACTION; COMBINED DESIGN; COUNTERIONS; DIETHYL ETHERS; FOLDAMERS; LAYER-BY-LAYER ASSEMBLIES; MOLECULAR SURFACES; NON-SOLVENTS; SOLVENT POLARITY; TYPE STRUCTURES;

METHANOL; OLEFINS; ORGANIC COMPOUNDS; SOLVENTS;

ETHERS;

EID: 71549147215     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma901954x     Document Type: Article

References (63)

1. For a recent review on ionenes, see: Williams, S. R.; Long, T. E. Prog. Polym. Sci. 2009, 34, 762.
2. Abboud, J. L. M.; Notario, R.; Bertran, J.; Sola, M. Prog. Phys. Org. Chem. 1993, 19, 1.
3. (a) Rembaum, A.; Baumgartner, W.; Eisenberg, A. J. Polym. Sci., Polym. Lett. Ed. 1968, 5, 159.
4. (b) Rembaum, A.; Noguchi, N. Macromolecules 1972, 5, 261.
5. (c) Noguchi, N.; Rembaum, A. J. Polym. Sci., Polym. Lett. Ed. 1969, 7, 383.
6. (a) Casson, D.; Rembaum, A. Macromolecules 1972, 5, 75.
7. (b) Eisenberg, A.; Hird, B.; Moore, R. B. Macromolecules 1990, 23, 4098.
8. (c) Knapick, E. G.; Hirsch, J. A.; Ander, P. Macromolecules 1985, 18, 1015.
9. (d) Williams, S. R.; Borgerding, E. M.; Layman, J. M.; Wang, W.; Winey, K. I.; Long, T. E. Macromolecules 2008, 41, 5216.
10. (e) Klun, T. C.; Wendling, L. A.; Van Bogart, J. W. C.; Robbins, A. F. J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 87.
11. (f) Grassl, B.; Galin, J. C. Macromolecules 1995, 28, 7035.
12. (g) Soldi, V.; Erismann, N. M.; Quina, F. H. J. Am. Chem. Soc. 1988, 110, 5137.
13. (h) Zhuomei, L.; Xuexin, Z.; Yuanpei, C.; Yuanzhen, Z. Macromolecules 1992, 25, 450.
14. (a) Kunitake, T.; Nakashima, N.; Takarabe, K.; Nagai, M.; Tsuge, A.; Yanagi, H. J. Am. Chem. Soc. 1981, 103, 5945.
15. (b) Kunitake, T.; Tsuge, A.; Takarabe, K. Polym. J. (Tokyo, Jpn.) 1985, 17, 633.
16. Hinze, W. L.; Moreno, B.; Quina, F. H.; Suzuki, Y.; Wang, H. Anal. Chem. 1994, 66, 3449.
17. Hong, J. D.; Jung, B. D.; Kim, C. H.; Kim, K. Macromolecules 2000, 33, 7905.
18. Wang, J.; Ober, C. K. Macromolecules 1997, 30, 7560.
19. (a) Suzuki, Y.; Tazuke, S. Macromolecules 1981, 14, 1742.
20. (b) Suzuki, Y.; Tazuke, S. Macromolecules 1980, 13, 25.
21. (a) Chen, L.; Yu, S.; Kagami, Y.; Gong, J.; Osada, Y. Macromolecules 1998, 31, 787.
22. (b) Yu, S. Y.; Hirata, M.; Chen, L.; Matsumoto, S.; Matsukata, M.; Gong, J. P.; Osada, Y. Macromolecules 1996, 29, 8021.
23. (c) Zheng, X.; Cao, W. Eur. Polym. J. 2001, 37, 2259.
24. (a) Zelikin, A. N.; Litmanovich, A. A.; Paraschuk, V. V.; Sybatchin, A. V.; Izumrudov, V. A. Macromolecules 2003, 36, 2066.
25. (b) Zelikin, A. N.; Putnam, D.; Shastri, P.; Langer, R.; Izumrudov, V. A. Bioconjugate Chem. 2002, 13, 548.
26. For comprehensive reviews on Foldamers, see: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
27. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Huges, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
28. (a)Wang, W.; Li, L. S.; Helms, G.; Zhou, H. H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120.
29. (b) Li, A. D. Q.; Wang, W.; Wang, L. Q. Chem.-Eur. J. 2003, 9, 4594.
30. (c) Neuteboom, E. E.; Meskers, S. C. J.; Meijer, E. W.; Janssen, R. A. J. Macromol. Chem. Phys. 2004, 205, 217.
31. (d) Balbo Block, M. A.; Hecht, S. Macromolecules 2004, 37, 4761.
32. (a) Ghosh, S.; Ramakrishnan, S. Angew. Chem., Int. Ed. 2005, 44, 5441.
33. (b) Ghosh, S.; Ramakrishnan, S. Angew. Chem., Int. Ed. 2004, 43, 3264.
34. (c) Ghosh, S.; Ramakrishnan, S. Macromolecules 2005, 38, 676.
35. (d) Ramkumar, S .G.; Ramakrishnan, S. J. Chem. Sci. 2008, 120, 187.
36. (a) Bradford, V. J.; Iverson, B. L. J. Am. Chem. Soc. 2008, 130, 1517.
37. (b) Gabriel, G. J.; Iverson, B. L. J. Am. Chem. Soc. 2002, 124, 15174.
38. (c) Zych, A. J.; Iverson, B. L. J. Am. Chem. Soc. 2000, 122, 8898.
39. (d) Nguyen, J. Q.; Iverson, B. L. J. Am. Chem. Soc. 1999, 121, 2639.
40. (e) Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303.
41. (a) Zhao, X.; Jia, M. X.; Jiang, X. K.; Wu, L. Z.; Li, Z. T.; Chen, G. J. J. Org. Chem. 2004, 69, 270.
42. (b) Zhou, Q. Z.; Jiang, X. K.; Shao, X. B.; Chen, G. J.; Jia, M. X.; Li, Z. T. Org. Lett. 2003, 5, 1955.
43. (a) Herrmann, W.; Keller, B.; Wenz, G. Macromolecules 1997, 30, 4966.
44. (b) Ikeda, Y.; Murakami, T.; Yuguchi, Y.; Kajiwara, K. Macromolecules 1998, 31, 1246.
45. (c) Pirogov, A. V.; Krokhin, O. V.; Platonov, M. M.; Deryugina, Ya. I.; Shpigun, O. A. J. Chromatogr., A 2000, 884, 31.
46. (d) Schulz, R. C.; Hochberg, G.; Walte, F. Angew. Makromol. Chem. 1994, 223, 177.
47. Buruiana, E. C.; Buruiana, T. Eur. Polym. J. 2001, 37, 2505.
48. Kanbara, T.; Kanayama, R.; Hasegawa, K. Polym. Bull. 1997, 38, 523.
49. For details of experimental procedures, computational methods, and NMR spectra, see the Supporting Information.
50. (a) Deperasinska, I.; Prochorow, J. Adv. Mol. Relax. Interact. Processes 1977, 11, 51.
51. (b) Sinanoglu, O. Molecular Association in Biology; Pullman, B., Ed.; Academic Press: New York, 1968; p 427.
52. (c) Cubberley, M. S.; Iverson, B. L. J. Am. Chem. Soc. 2001, 123, 7560.
53. Here the polarity of the solvent is reflected more by their relative ability to solvate the polymer chains (solubility parameter δ) rather than the dielectric constant of the solvent.
54. Litt, M. H.; Wellinghoff, J. J. Phys. Chem. 1977, 81, 2644.
55. The value of e was varied to achieve the best fit in the van't Hoff plot of 1n K versus 1/T. See the Supporting Information for details.
56. -1. Pascu, S. I.; Jarrosson, T.; Naumann, C.; Otto, S.; Kaiser, G.; Sanders, J. K. M. New J. Chem. 2005, 29, 80.
57. The average value of the height by sampling a large number of aggregates was found to be 3.5 nm, whereas the average diameter was 135 nm. See the Supporting Information for a detailed tabulation along with AFM images. Hong et al. (ref 7) also observed aggregates of similar thickness in their azobenzene bearing ionenes.
58. For recent examples, see: (a) Harth, E.; Horn, B. V.; Lee, V. Y.; Germack, D. S.; Gonzales, C. P.; Miller, R. D.; Hawker, C. J. J. Am. Chem. Soc. 2002, 124, 8653.
59. (b) Beck, J. B.; Killops, K. L.; Kang, T.; Sivanandan, K.; Bayles, A.; Mackay, M. E.; Wooley, K. L.; Hawker, C. J. Macromolecules 2009, 42, 5629.
60. (c) Cherian, A. E.; Sun, F. C.; Sheiko, S. S.; Coates, G. W. J. Am. Chem. Soc. 2007, 129, 11350.
61. Foster, E. J.; Berda, E. B.; Meijer, E. W. J. Am. Chem. Soc. 2009, 131, 6964.
62. (a) Peyratout, C. S.; Dähne, L. Angew. Chem., Int. Ed. 2004, 43, 3762.
63. (b) Quinn, J. F.; Johnston, A. P. R.; Such, G. K.; Zelikin, A. N.; Caruso, F. Chem. Soc. Rev. 2007, 36, 707.