Aggregation, complexation with guest molecules, and mesomorphism of amphiphilic phthalocyanines having four- or eight tri(ethylene oxide) chains

Bulletin of the Chemical Society of Japan

Volumn 72, Issue 6, 1999, Pages 1263-1271

  Kobayashi, Nagao ^a   Higashi, Ryuji ^a   Ishii, Kazuyuki ^a   Hatsusaka, Kazuaki ^b   Ohta, Kazuchika ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOPHILE; ETHYLENE OXIDE; PHTHALOCYANINE DERIVATIVE;

ABSORPTION; ARTICLE; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CRYSTALLIZATION; ENVIRONMENTAL TEMPERATURE; FLUORESCENCE SPECTROSCOPY; HYDROGEN BOND; ISOMER; PHASE TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

EID: 0032989307     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.1263     Document Type: Article

References (72)

1. a) "Phthalocyanines - Properties and Applications," ed by C. C. Leznoff and A. B. P. Lever, VHC Publications, New York (1989);
2. b) Vol. 2 (1993);
3. c) Vol. 3 (1993);
4. d) Vol. 4 (1996);
5. e) "Phthalocyanines - Chemistry and Applications," ed by H. Shirai and N. Kobayashi, IPC, Tokyo (1997).
6. a) J. M. Kroon, R. B. M. Koehorst, M. van Dijk, G. M. Sanders, and E. J. Sundholter, J. Mater. Chem., 7, 615 (1997);
7. b) S. F. Foley, G. Jones, R. Liuzzi, D. J. McGarvey, M. H. Perry, and T. G. Truscott, J. Chem. Soc., Perkin Trans. 2, 1997, 1725.
8. a) N. Kobayashi and A. B. P. Lever, J. Am. Chem. Soc., 109, 7433 (1987);
9. b) T. Toupance, V. Ahsen, and J. Simon, J. Am. Chem. Soc., 116, 5352 (1994).
10. a) C. Piechochi, J. Simon, A. Skoulious, D. Guillan, and P. Weber, J. Am. Chem. Soc., 119, 7281 (1997);
11. b) M. J. Cook, N. B. McKeown, A. J. Thomson, K. J. Harrison, R. M. Richardson, A. N. Davies, and S. J. Roser, Chem. Mater., 1, 287 (1989);
12. c) T. Toupance, P. Bassoul, L. Mineau, and J. Simon, J. Phys. Chem., 100, 11704 (1996).
13. D. Guillon, P. Weber, A. Skoulionus, C. Piechocki, and J. Simon, Mol. Cryst. Liq. Cryst., 130, 223 (1985); C. Piechocki and J. Simon, J. Chem. Soc., Chem. Commun., 1985, 259.
14. D. Guillon, P. Weber, A. Skoulionus, C. Piechocki, and J. Simon, Mol. Cryst. Liq. Cryst., 130, 223 (1985); C. Piechocki and J. Simon, J. Chem. Soc., Chem. Commun., 1985, 259.
15. a) N. B. McKeown and J. Painter, J. Mater. Chem., 4, 1153 (1994);
16. b) H. Eichorn, D. Wöhrle, and D. Pressner, Liq. Cryst., 22, 643 (1997);
17. c) N. B. McKeown, C. C. Leznoff, R. M. Richardson, and A. S. Cherodian, Mol. Cryst. Liq. Cryst., 213, 91 (1992);
18. d) G. J. Clarkson, B. M. Hassan, D. R. Maloney, and N. B. McKeown, Macromolecules, 29, 1854 (1996).
19. N. Kobayashi, T. Ohya, M. Sato, and S. Nakajima, Inorg. Chem., 32, 1803 (1993).
20. a) P. G. Seybold and M. Gouterman, J. Mol. Spectrosc., 31, 1 (1969);
21. b) W. Melhuish, J. Phys. Chem., 64, 762 (1960);
22. c) J. N. Demas and G. A. Crosby, J. Phys. Chem., 75, 991 (1971).
23. H. Erna, Master Thesis, Shinsyu University, Ueda, Japan, 1988; H. Hasebe, Master Thesis, Shinsyu University, Ueda, Japan, 1991.
24. H. Erna, Master Thesis, Shinsyu University, Ueda, Japan, 1988; H. Hasebe, Master Thesis, Shinsyu University, Ueda, Japan, 1991.
25. M. J. Stillman and T. Nyokong, "Phthalocyanines - Properties and Applications," ed by C. C. Leznoff and A. B. P. Lever, VCH Publications, New York (1989), pp. 135-289.
26. M. Hanack, G. Schmid, and M. Sommerauer, Angew. Chem., Int. Ed. Engl., 32, 1422 (1993); M. Sommerauer, C. Rager, and M. Hanack, J. Am. Chem. Soc., 118, 10085 (1996).
27. M. Hanack, G. Schmid, and M. Sommerauer, Angew. Chem., Int. Ed. Engl., 32, 1422 (1993); M. Sommerauer, C. Rager, and M. Hanack, J. Am. Chem. Soc., 118, 10085 (1996).
28. a) N. Kobayashi, Y. Yanagisawa, T. Osa, H. Lam, and C. C. Leznoff, Anal. Sci., 6, 813 (1990);
29. b) N. Kobayashi, H. Lam, W. A. Nevin, P. Janda, C. C. Leznoff, and A. B. P. Lever, Inorg. Chem., 29, 3415 (1990).
30. E. S. Dodsworth and A. B. P. Lever, J. Phys. Chem., 89, 5698 (1985).
31. N. J. Turro, "Modern Molecular Photochemistry," University Science Books, California (1991).
32. N. Kobayashi and H. Konami, "Phthalocyanines - Properties and Applications," ed by C. C. Leznoff and A. B. P. Lever, VCH Publications, New York (1996), Vol. 4, pp. 343-404.
33. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
34. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
35. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
36. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
37. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
38. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
39. K. Toyota, J. Hasegawa, and H. Nakatsuji, J. Phys. Chem., 101, 446 (1997); N. Ishikawa, O. Ohno, and Y. Kaizu, J. Phys. Chem., 97, 1004 (1993); A. Rosa and E. Baerends, Inorg. Chem., 31, 4717 (1992); E. Orti, J. L. Bredas, and C. Clarisse, J. Chem. Phys., 92, 1228 (1990); L. K. Lee, N. H. Sabelli, and P. R. LeBreton, J. Phys. Chem., 86, 3926 (1982); A. M. Schaffer, M. Gouterman, and E. Davidson, Theor. Chim. Acta, 30, 9 (1973); A. M. Schaffer and M. Gouterman, Theor. Chim. Acta, 25, 62 (1972).
40. A. Tajiri and J. Winkler, Z. Naturforsh., A, 38a, 1263 (1983).
41. N. Kobayashi, M. Togashi, T. Osa, K. Ishii, S. Yamauchi, and H. Hino, J. Am. Chem. Soc., 118, 1073 (1996).
42. S. B. Piepho and P. N. Schatz, "Group Theory in Spectroscopy with Applications to Magnetic Circular Dichroism," Wiley, New York (1983).
43. Emission from dimer is generally very weak, if any: N. E. Kagan, D. Mauzerall, and R. B. Merrifield, J. Am. Chem. Soc., 99, 5486 (1977). However, an exceptional emission from tetra-sulfonated [Zn(pc)] dimer was reported recently; Y. Kaneko, T. Arai, K. Tokumaru, D. Matsunaga, and H. Sakuragi, Chem. Lett., 1996, 345.
44. Emission from dimer is generally very weak, if any: N. E. Kagan, D. Mauzerall, and R. B. Merrifield, J. Am. Chem. Soc., 99, 5486 (1977). However, an exceptional emission from tetra-sulfonated [Zn(pc)] dimer was reported recently; Y. Kaneko, T. Arai, K. Tokumaru, D. Matsunaga, and H. Sakuragi, Chem. Lett., 1996, 345.
45. Y. Kaneko, Y. Nishimura, N. Takane, T. Arai, H. Sakuragi, N. Kobayashi, D. Matsunaga, C. Pac, and K. Tokumaru, J. Photochem. Photobiol. A: Chem., 106, 177 (1977).
46. N. Kobayashi, H. Lam, W. A. Nevin, P. Janda, C. C. Leznoff, T. Koyama, A. Monden, and H. Shirai, J. Am. Chem. Soc., 116, 879 (1994).
47. F. Perrin, J. Phys. Radium., 7, 390 (1962); I. B. Berlman, Mol. Cryst., 4, 157 (1968).
48. F. Perrin, J. Phys. Radium., 7, 390 (1962); I. B. Berlman, Mol. Cryst., 4, 157 (1968).
49. a) K. Sauer, J. R. L. Smith, and A. J. Schultz, J. Am. Chem. Soc., 88, 2681 (1966);
50. b) J. A. Shelnutt, M. M. Dobry, and J. D. Satterlee, J. Phys. Chem., 88, 4980 (1984).
51. f0 =0.90).
52. Benzoquinone derivatives can generally quench the fluorescence of phthalocyanines; see for example: Ref. 7 and N. Kobayashi, Y. Nishiyama, T. Ohya, and M. Sato, J. Chem. Soc., Chem. Commun., 1987, 390.
53. T. G. Edward and R. Grinter, Trans. Faraday Soc., 64, 1070 (1968).
54. T. Koyama, T. Suzuki, K. Hanabusa, H. Shirai, and N. Kobayashi, lnorg. Chim. Acta, 218, 41 (1994); T. Sauer and G. Wegner, Mol. Cryst. Liq. Cryst., 162, 97 (1988); E. A. Cuellar and T. J. Marks, Inorg. Chem., 20, 3766 (1981); J. E. Maskasy, J. R. Mooney, and M. E. Kenney, J. Am. Chem. Soc., 94, 2132 (1972); T. R. Janson, A. R. Kane, J. F. Sullivan, K. Knox, and M. E. Kenney, J. Am. Chem. Soc., 91, 5210 (1969).
55. T. Koyama, T. Suzuki, K. Hanabusa, H. Shirai, and N. Kobayashi, lnorg. Chim. Acta, 218, 41 (1994); T. Sauer and G. Wegner, Mol. Cryst. Liq. Cryst., 162, 97 (1988); E. A. Cuellar and T. J. Marks, Inorg. Chem., 20, 3766 (1981); J. E. Maskasy, J. R. Mooney, and M. E. Kenney, J. Am. Chem. Soc., 94, 2132 (1972); T. R. Janson, A. R. Kane, J. F. Sullivan, K. Knox, and M. E. Kenney, J. Am. Chem. Soc., 91, 5210 (1969).
56. T. Koyama, T. Suzuki, K. Hanabusa, H. Shirai, and N. Kobayashi, lnorg. Chim. Acta, 218, 41 (1994); T. Sauer and G. Wegner, Mol. Cryst. Liq. Cryst., 162, 97 (1988); E. A. Cuellar and T. J. Marks, Inorg. Chem., 20, 3766 (1981); J. E. Maskasy, J. R. Mooney, and M. E. Kenney, J. Am. Chem. Soc., 94, 2132 (1972); T. R. Janson, A. R. Kane, J. F. Sullivan, K. Knox, and M. E. Kenney, J. Am. Chem. Soc., 91, 5210 (1969).
57. T. Koyama, T. Suzuki, K. Hanabusa, H. Shirai, and N. Kobayashi, lnorg. Chim. Acta, 218, 41 (1994); T. Sauer and G. Wegner, Mol. Cryst. Liq. Cryst., 162, 97 (1988); E. A. Cuellar and T. J. Marks, Inorg. Chem., 20, 3766 (1981); J. E. Maskasy, J. R. Mooney, and M. E. Kenney, J. Am. Chem. Soc., 94, 2132 (1972); T. R. Janson, A. R. Kane, J. F. Sullivan, K. Knox, and M. E. Kenney, J. Am. Chem. Soc., 91, 5210 (1969).
58. T. Koyama, T. Suzuki, K. Hanabusa, H. Shirai, and N. Kobayashi, lnorg. Chim. Acta, 218, 41 (1994); T. Sauer and G. Wegner, Mol. Cryst. Liq. Cryst., 162, 97 (1988); E. A. Cuellar and T. J. Marks, Inorg. Chem., 20, 3766 (1981); J. E. Maskasy, J. R. Mooney, and M. E. Kenney, J. Am. Chem. Soc., 94, 2132 (1972); T. R. Janson, A. R. Kane, J. F. Sullivan, K. Knox, and M. E. Kenney, J. Am. Chem. Soc., 91, 5210 (1969).
59. J. T. Arnold and M. E. Packard, J. Phys. Chem., 19, 1680 (1951); A. D. Chohen and C. Reid, J. Phys. Chem., 25, 790 (1956).
60. J. T. Arnold and M. E. Packard, J. Phys. Chem., 19, 1680 (1951); A. D. Chohen and C. Reid, J. Phys. Chem., 25, 790 (1956).
61. If many BINAP molecules are fixed around pc molecules, strong induced CD signal will be recorded as shown in: N. Kobayashi, Y. Kobayashi, and T. Osa, J. Am. Chem. Soc., 115, 10994 (1993).
62. a) J. Billard, C. R. Acad. Sci. Paris, 299, 905 (1984);
63. b) H. Sakashita, A. Nishitani, Y. Sumiya, H. Terauchi, K. Ohta, and I. Yamamoto, Mol. Cryst. Liq. Cryst., 163, 211 (1988);
64. c) K. Ohta, R. Higashi, M. Ikejima, I. Yamamoto, and N. Kobayashi, J. Mater. Chem., 8, 1979 (1998); Y. Shimizu, A. Ishikawa, and S. Kusabayashi, Chem. Lett., 1986, 1041;
65. c) K. Ohta, R. Higashi, M. Ikejima, I. Yamamoto, and N. Kobayashi, J. Mater. Chem., 8, 1979 (1998); Y. Shimizu, A. Ishikawa, and S. Kusabayashi, Chem. Lett., 1986, 1041;
66. d) M. Veber, R. Fugnitto, and H. Strzelecka, Mol. Cryst. Liq. Cryst., 96, 211 (1983);
67. e) K. Ohta, A. Takagi, H. Muroki, I. Yamamoto, K. Matsuzaki, T. Inabe, and Y. Maruyama, J. Chem. Soc., Chem. Commn., 1986, 883;
68. f) X,-Q. Wang, C.-S. Cao, S. Gao, T.-S. Shi, T.-S.L.-X. Yu, and X. Z. Cao, Chem. J. Chin. Univ., 17, 684 (1996).
69. a) C. C. Leznoff, M. Hu, C. R. McArther, Y. Qin, and J. E. van Lier, Can. J. Chem., 72, 1990 (1994);
70. b) K. Kasuga, K. Asano, L. Lin, T. Sugimori, M. Hanada, K. Abe, T. Kikkawa, and T. Fujiwara, Bull. Chem. Soc. Jpn., 70, 1859 (1997).
71. W. C, MacCrone, "Physics and Chemistry of the Organic Solid State," ed by D. Fox, M. Labess, and A, Weissberger, John Wiley & Sons, New York (1965), Vol. II, pp. 725-766.
72. "The Nature of Chemical Bond and the Structure of Molecules and Crystals: An Introduction to Modern Structural Chemistry," 3rd ed, ed by L. Pauling, Cornell Univ. Press, New York (1960).