Marked effect of aromatic solvent on unfolding rate of helical ethynylhelicene oligomer

Journal of the American Chemical Society

Volumn 126, Issue 45, 2004, Pages 14858-14864

  Sugiura, Hiroki ^a   Nigorikawa, Yasuko ^a   Saiki, Yuto ^a   Nakamura, Keiichi ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; RATE CONSTANTS; SOLVENTS; TOLUENE;

AROMATIC SOLVENTS; CD SPECTRA; CHLOROBENZENE; REACTION RATES;

OLIGOMERS;

ANISOLE DERIVATIVE; AROMATIC COMPOUND; BENZENE; BENZENE DERIVATIVE; BENZONITRILE; BENZOTRIFLUORIDE; BROMOBENZENE; CHLOROBENZENE; CHLOROFORM; DIFLUOROBENZENE; ETHYL BENZOATE; ETHYLBENZENE; ETHYNYLHELICENE; FLUOROBENZENE; HALOBENZENE; IODOBENZENE; OLIGOMER; PHENYLACETYLENE; SOLVENT; STYRENE; THIOANISOLE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONCENTRATION RESPONSE; CORRELATION ANALYSIS; DIMERIZATION; HARDNESS; OPTICS; POLYMERIZATION; PRODUCT RECOVERY; ROOM TEMPERATURE; SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS; VAPOR PRESSURE;

EID: 8844251450     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0478882     Document Type: Article

References (56)

1. Recent examples of conformational changes of peptides in aqueous solutions: (a) Dyson, H. J.; Merutka, G.; Waltho, J. P.; Lernen, R. A.; Wright, P. E. J. Mol. Biol. 1992, 226, 795-817.
2. (b) Shiraki, K.; Nishikawa, K.; Goto, Y. J. Mol. Biol. 1995, 245, 180-194.
3. (c) Konno, T.; Tanaka, N.; Kataoka, M.; Takano, E.; Maki, M. Biochim. Biophys. Acta 1997, 1342, 73-82.
4. (d) Schreiber, J. V.; Seebach, D. Helv. Chim. Acta 2000, 83, 3139-3152.
5. Recent examples of conformational changes of peptides in organic solvents: (a) Ikeda, K.; Ogoma, Y.; Fujii, T.; Hachimori, A.; Kondo, Y.; Hayakawa, T.; Iwatsuki, M.; Akaike, T. Polymer 1990, 31, 344-347.
6. (b) Kemp, D. S.; Curran, T. P.; Boyd, J. G.; Allen, T. J. J. Org. Chem. 1991, 56, 6683-6697.
7. (c) Tamaki, M.; Komiya, S.; Yabu, M.; Watanabe, E.; Akabori, S.; Muramatsu, I. J. Chem. Soc., Perkin Trans, 1 1997, 3497-3500.
8. (d) Tamaki, M.; Yabu, M.; Saeki, T.; Kaneko, A.; Akabori, S.; Muramatsu, I. Bull. Chem. Soc. Jpn. 1999, 72, 733-739.
9. (e) Milne, B. F.; Morris, L. A.; Jaspars, M.; Thompson, G. S. J. Chem. Soc., Perkin Trans. 2 2002, 1076-1080.
10. (f) Crespo, J. S.; Lecommandoux, S.; Borsali, R.; Klok, H.-A.; Soldi, V. Macromolecules 2003, 36, 1253-1256.
11. Conformational changes in organic solvents of phenylene ethynylene oligomers by Moore, J. S.: (a) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
12. (b) Prince, R. B.; Saven, J. G.; Wolynes, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114-3121.
13. (c) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319.
14. (d) Brunsveld, L.; Prinde, R. B.; Maijer, E. W.; Moore, J. S. Org. Lett. 2000, 2, 1525-1528.
15. (e) Hill, D. J.; Moore, J. S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5053-5057.
16. Also see, (f) Zhang, H.; Lu, X.; Li, Y.; Ai, X.; Zhang, X.; Yang, G. J. Photochem. Photobiol. A 2002, 147, 15-23.
17. (g) Roy, B. C.; Gupta, M. D.; Bhoumik, L.; Ray, J. K. Synth. Met. 2002, 130, 27-33.
18. (h) Chu, Q.; Pang, Y. Macromolecules 2003, 36, 4614-4618.
19. For examples of conformational changes of polypeptides with relatively high solvent dependences on rate: (a) Yang, W. W.-Y.; Overberger, C. G.; Venkatachalam, C. M. J. Polym. Sci., Polym. Chem. Ed. 1983, 21, 1741-1749.
20. (b) Killian, J. A.; Prasad, K. U.; Hains, D.; Urry, D. W. Biochemistry 1988, 27, 4848-4855.
21. (c) Meyer, T. E.; Tollin, G.; Hazzard, J. H.; Cusanovich, M. A. Biophys. J. 1989, 56, 559-564.
22. (d) Ansari, A.; Jones, C. M.; Henry, E. R.; Hofrichter, J.; Eaton, W. A. Science 1992, 256, 1796-1798.
23. (e) Xu, F.; Wang, A.; Vaughn Jr., J. B.; Cross, T. A. J. Am. Chem. Soc. 1996, 118, 9176-9177.
24. Israëli, Y.; Detellier, C. Phys. Chem. Chem. Phys. 2004, 6, 1253-1257.
25. Kojima, S.; Doi, Y.; Okuda, M.; Akiba, K. Organometallics 1995, 14, 1928-1937.
26. (a) Tashiro, K.; Yoshioka, A. Macromolecules 2002, 35, 410-414.
27. (b) Tashiro, K.; Yoshioka, A.; Hashida, T. Macromol. Symp. 2003, 203, 13-25.
28. Kobayashi, M. Macromol. Symp. 1997, 114, 1-12.
29. Shen, C.-L.; Murphy, R. M. Biophys. J. 1995, 69, 640-651.
30. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Weinheim, 1988.
31. (a) Grate, J. W.; McGill, R. A.; Hilvert, D. J. Am. Chem. Soc. 1993, 115, 8577-8584.
32. (b) Zipse, H.; Apaydin, G.; Houk, K. N. J. Am. Chem. Soc. 1995, 117, 8608-8617.
33. (c) Katritzky, A. R.; Perumal, S.; Petrukhin, R. J. Org. Chem. 2001, 66, 4036-4040.
34. (a) Dubois, J.-E.; Garnier, F. Chem. Commun. 1968, 241-242.
35. (b) Ruasse, M.-F.; Dubois, J.-E. J. Am. Chem. Soc. 1975, 97, 1977-1978.
36. (a) Fainberg, A. H.; Winstein, S. J. Am. Chem. Soc. 1956, 78, 2770-2777.
37. (b) Abraham, M. H. J. Chem. Soc., Perkin Trans. 2 1972, 1343-1357.
38. Nakamura, K.; Okubo, H.; Yamaguchi, M. Org. Lett. 2001, 3, 1097-1099.
39. (a) Saiki, Y.; Nakamura, K.; Nigorikawa, Y.; Yamaguchi, M. Angew. Chem., Int. Ed. 2003, 42, 5190-5192.
40. (b) Saiki, Y.; Sugiura, H.; Nakamura, K.; Yamaguchi, M.; Hoshi, T.; Anzai, J. J. Am. Chem. Soc. 2003, 125, 9268-9269.
41. (a) Berl, V.; Hue, I.; Khoury, R. G.; Lehn, J.-M. Chem.-Eur. J. 2001, 7, 2798-2809.
42. (b) Dolain, C.; Maurizot, V.; Hue, I. Angew. Chem., Int. Ed. 2003, 42, 2738-2740.
43. (c) Kolomiets, E.; Berl, V.; Odriozola, I.; Stadler, A.-M.; Kyritsakas, N.; Lehn, J.-M. Chem. Commun. 2003, 2868-2869.
44. (d) Yuan, G.-L.; Kuramoto, N. Polymer 2003, 44, 5501-5504.
45. (a) Yashima, E.; Goto, H.; Okamoto, Y. Macromolecules 1999, 32, 7942-7945.
46. (b) Goto, H.; Okamoto, Y.; Yashima, E. Chem.-Eur. J. 2002, 8, 4027-4036.
47. (c) Kawamura, H.; Ishikawa, M.; Maeda, K.; Yashima, E. Chem. Lett. 2003, 32, 1086-1087.
48. See also the following reviews for helix formation: (a) Piguet, C.; Bernardinelli, G.; Hopfgartner, G. Chem. Rev. 1997, 97, 2005-2062.
49. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
50. (c) Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039-4070.
51. Nakamura, K.; Okubo, H.; Yamaguchi, M. Synlett 1999, 549-550.
52. Aggregation of phenylene ethynylene macrocycles in aromatic solvents. (a) Tobe, Y.; Utsumi, N.; Kawabata, K.; Naemura, K. Tertahedron Lett. 1996, 37, 9325-9328.
53. (b) Lahiri, S.; Thompson, J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315-11319.
54. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350-5364.
55. See Supporting Information.
56. Pearson, R. G. J. Org. Chem. 1989, 54, 1423-1430.