Aggregation of conjugated helical molecules

Journal of the American Chemical Society

Volumn 118, Issue 15, 1996, Pages 3767-3768

  Nuckolls, Colin ^a   Katz, Thomas J ^a   Castellanos, Louis ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CIRCULAR DICHROISM; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

EID: 0029904378     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960145z     Document Type: Article

References (62)

1. (a) Chandrasekhar, S. Liq. Cryst. 1993, 14, 3 and references therein.
2. (b) Destrade, C.; Foucher, P.; Gasparoux, H.; Tinh, N. H.; Levelut, A. M.; Malthete, J. Mol. Cryst. Liq. Cryst. 1984, 106, 121.
3. (c) Espinet, P.; Esteruelas, M. A.; Oro, L. A.; Serrano, J. L.; Sola, E. Coord. Chem. Rev. 1992, 117, 215.
4. (d) Serrette, A. G.; Lai, C. K.; Swager, T. M. Chem. Mater. 1994, 6, 2252.
5. Willmore, N. D.; Liu, L.; Katz, T. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1093.
6. (a) Green, M. M.; Ringsdorf, H.; Wagner, J., Wüstefeld, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 1478 and references therein.
7. (b) Markovitsi, D.; Bengs, H., Ringsdorf, H. J. Chem. Soc., Faraday Trans. 1992, 88, 1275.
8. (c) Gallivan, J. P.; Schuster, G. B. J. Org. Chem. 1995, 60, 2423.
9. (a) Amphotericin: Rinnert, H.; Thirion. C.; DuPont, G.; Lematre, J. Biopolymers 1977, 16, 2419.
10. (b) An anthocyanin: Goto, T.; Tamura, H.; Kawai, T.; Hoshino, T.; Harada, N; Kondo, T. Ann. NY Acad. Sci. 1986, 471, 155.
11. (c) Some acridines: Jodál, I.; Kovács, A; Ott, J.; Snatzke, G. Chem. Ber. 1989, 122, 1207.
12. (d) A stilbene fatty acid: Song, X.; Geiger, C.; Leinhos, U.; Perlstein, J.; Whitten, D. G. J. Am. Chem. Soc. 1994, 116, 10340.
13. (a) Yuzhakov, V. I. Russ. Chem. Rev. 1979, 48, 1076.
14. (b) Möbius, D. Adv. Mater. 1995, 7, 437.
15. (c) Cook, M. J. In Spectroscopy of New Materials, Clark, R. J. H., Hester, R. E., Eds.; Wiley: New York, 1993; Chapter 3.
16. (d) Daltrozzo, E.; Scheibe, G.; Gschwind, K., Haimerl, F. Photogr. Sci. Eng. 1974, 18, 441.
17. (e) Makio, S.; Kanamaru, N.; Tanaka, J. Bull. Chem. Soc. Jpn. 1980, 53, 3120.
18. (f) Sheppard, S. E.; Geddes, A. L. J. Am. Chem. Soc. 1944, 66, 1995.
19. (g) McKay, R. B.; Hillson, P. J Trans. Faraday Soc. 1965, 61, 1800.
20. (h) Schutte, W. J.; Sluyters-Rehbach, M., Sluyters, J. H. J. Phys. Chem. 1993, 97, 6069.
21. (i) Das, S.; Thanulingam, T. L; Thomas, K. G.; Kamat, P. V.; George, M. V J. Phys. Chem. 1993, 97, 13620.
22. (j) Herz, A. H. Photogr. Sci. Eng 1974, 18, 323
23. On concentration, the fluorescence emission maximum shifts from 415 to 472 nm.
24. Scheibe, G. Kolloid-Z. 1938, 82, 1.
25. Pasternack, R. F.; Collings, P. J. Science 1995, 269, 935. We thank Prof. Collings for the preliminary result, whose details will be published separately.
26. Solutions of numerous amphiphiles and a few other molecules form fibers comprised of solute and solvent, but we could find no reports of fibers, like those pictured, that form in the absence of solvents.
27. Examples are in the following and in the references cited therein, (a) Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565.
28. (b) Menger, F. M.; Lee, S. S.; Tao, X. Adv. Mater. 1995, 7, 669.
29. (c) Snijder, C. S.; de Jong, J. C.; Meetsma, A., van Bolhuis, F.; Feringa, B. L. Chem. Eur. J. 1995, 1, 594.
30. (d) Hanabusa, K.; Okui, K.; Karaki, K: Koyama, T.; Shirai, H. J. Chem. Soc., Chem. Commun. 1992, 1371.
31. (e) Lin, Y., Kachar, B.; Weiss, R. G. J. Am. Chem. Soc. 1989, 111, 5542.
32. (f) Brotin, T.; Utermöhlen, R.; Fages, F.; Bouas-Laurent, H; Desvergne, J.-P. J. Chem. Soc., Chem. Commun. 1991, 416.
33. (g) Jelley, E. E. Nature 1937, 139, 631.
34. No other phase transitions between 25 and 200°C were found by polarization microscopy or between 0 and 210°C by DSC (scanned for two cycles at 10 deg/min), the latter implying that if any occur, they involve either little change in enthalpy or are slow. We thank Prof. Timothy Swager for the experiment.
35. Estimated by Dr. N. D. Willmore, Harvard University.
36. The solutions when sandwiched between crossed polarizers transmit no light. Their specific rotation is unchanged by a 90° turn of the cell.
37. 4 in the concentrated one.
38. (a) Nakahara, H.; Fukuda, K, Mobius, D, Kuhn, H. J. Phys. Chem. 1986, 90, 6144.
39. (b) Chiefari, J.; Griebenow, K., Griebenow, N.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. J. Phys Chem. 1995, 99, 1375 and references cited therein.
40. Kasha, M. Radiation Res. 1963, 20, 55 and references therein.
41. Splitting is observed when, as in refs 4 (for amphotericin also see ref 18) and 19, the vectors are not parallel. It is not observed in J-aggregates (see refs 5b,d and 20)
42. Brittain, H. G. Chirality 1994, 6, 665
43. (a) Chen, H; Law, K-Y., Perlstein, J, Whitten, D. G. J. Am. Chem. Soc. 1995, 117, 7257.
44. (b) Balaban, F S.; Holzwarth, A. R, Schaffner, K. J. Mol. Struct. 1995, 349, 183
45. Saeva, F. D.; Olin, G. R.; Turner, S. R.; Yanus, J. F.; Sandman, D. J. Photogr. Sci. Eng. 1978, 22, 129.
46. (a) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy - Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
47. (b) Hatano, M. Adv. Polym. Sci. 1986, 77, 1.
48. 26.
49. (a) Schweizer, M. P.; Broom, A. D.; Ts'o, P. O. P.; Hollis, D. P. J. Am. Chem. Soc. 1968, 90, 1042 and references therein.
50. (b) Hoshino, T.; Matsumoto, U. Goto, T.; Harada, N. Tetrahedron Lett. 1982, 23, 433.
51. (c) Patel, D. J. Acc. Chem. Res. 1979, 12, 118.
52. (d) Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986; pp 28-36.
53. Ito, H.; Agatsuma, M.; I'Haya, Y. J. Bull. Chem. Soc. Jpn. 1991, 64, 3700.
54. Another possibility is that the intermolecular electronic coupling is comparable to or smaller than the intramolecular vibronic coupling (Simpson, W. T.; Peterson, D. L. J. Chem. Phys. 1957, 26, 588).
55. 2 area.
56. Calculated assuming the density to be 0.85 g/mL.
57. The figures for 8 are reproducible and unchanged when samples are sheared in different directions. Prof. Collings found that at 633 nm, samples of 8 exhibit specific rotations as high as 2000 deg/mm. We thank him for the information.
58. (a) de Vries, H. Acta Crystallogr. 1951, 4, 219.
59. (b) Chandrasekhar, S.; Prasad, J. S. Mol. Cryst. Liq. Cryst. 1971, 14, 115.
60. (c) Isaert, N.; Berthault, J.-P.; Billard, J. J. Opt. 1980, 11, 17.
61. (d) Cano, R.; Chatelain, P. Compt. Rend. 1964, 259, 352.
62. (e) Baessler, H.; Laronge, T. M.; Labes, M M. J. Chem. Phys. 1969, 51, 3213.