Functional supramolecular materials: Self-assembly of phthalocyanines and porphyrazines

Chemical Communications

Volumn , Issue 21, 1996, Pages 2385-2392

  Van Nostrum, Cornelus F ^a   Nolte, Roeland J M ^a,b,c  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542608349     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002385     Document Type: Article

References (84)

1. (a) J.-M. Lehn, Angew. Chem., 1988, 100, 91; Angew. Chem., Int. Ed. Engl., 1988, 27, 89;
2. (a) J.-M. Lehn, Angew. Chem., 1988, 100, 91; Angew. Chem., Int. Ed. Engl., 1988, 27, 89;
3. (b) H. Ringsdorf, B. Schlarb and J. Venzmer, Angew. Chem., 1988, 100, 117; Angew. Chem., Int. Ed. Engl., 1988, 27, 113;
4. (b) H. Ringsdorf, B. Schlarb and J. Venzmer, Angew. Chem., 1988, 100, 117; Angew. Chem., Int. Ed. Engl., 1988, 27, 113;
5. (c) J. Simon, J.-J. André and A. Skoulios, New J. Chem., 1986, 10, 295.
6. (a) G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 1991, 254, 1312;
7. (b) J. S. Lindsey, New J. Chem., 1991, 15, 153;
8. (c) J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304;
9. (c) J.-M. Lehn, Angew. Chem., 1990, 102, 1347; Angew. Chem., Int. Ed. Engl., 1990, 29, 1304;
10. (d) M. R. Ghadiri, J. R. Granja and L. K. Buehler, Nature, 1994, 369, 301;
11. (e) M. Jørgensen, K. Bechgaard, T. Bjornholm, P. Sommer-Larsen, L. G. Hansen and K. Schaumburg, J. Org. Chem., 1994, 59, 5877;
12. (f) C. F. van Nostrum, S. J. Picken and R. J. M. Nolte, Angew. Chem., 1994, 106, 2298; Angew. Chem., Int. Ed. Engl., 1994, 33, 2173.
13. (f) C. F. van Nostrum, S. J. Picken and R. J. M. Nolte, Angew. Chem., 1994, 106, 2298; Angew. Chem., Int. Ed. Engl., 1994, 33, 2173.
14. C. J. Pedersen, J. Am. Chem. Soc., 1967, 89, 7017.
15. Phthalocyanines, Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH, New York, 1989-1993, vol. 1-3.
16. C. Piechocki, J. Simon, A. Skoulios, D. Guillon and P. Weber, J. Am. Chem. Soc., 1982, 104, 5245.
17. (a) J. F. van der Pol, E. Neeleman, J. W. Zwikker, R. J. M. Nolte and W. Drenth, Recl. Trav. Chim. Pays-Bas, 1988, 107, 615;
18. (b) J. F. van der Pol, E. Neeleman, J. W. Zwikker, R. J. M. Nolte, W. Drenth, J. Aerts, R. Visser and S. J. Picken, Liq. Cryst., 1989, 6, 577.
19. (a) M. K. Engel, P. Bassoul, L. Bosio, H. Lehmann, M. Hanack and J. Simon. Liq. Cryst., 1993, 15, 709;
20. (b) P. Weber, D. Guillon and A. Skoulios, Liq. Cryst., 1991, 9, 3.
21. M. J. Cook. J. Mater. Sci., Mater. Electron., 1994, 5, 117.
22. A. P. M. Kentgens, B. A. Markies, J. F. van der Pol and R. J. M. Nolte, J. Am. Chem. Soc., 1990, 112, 8800.
23. (a) P. Doppelt and S. Huille, New J. Chem., 1990, 14, 607;
24. (b) F. Lelj, G. Morelli, G. Ricciardi, A. Roviello and A. Sirigu, Liq. Cryst., 1992, 12, 941.
25. (a) A. N. Cammidge, M. J. Cook, K. J. Harrison and N. B. McKeown, J. Chem. Soc., Perkin Trans. 1, 1991, 3053;
26. (b) I. Cho and Y. Lim, Mol. Cryst. Liq. Cryst., 1988, 154, 9;
27. (c) W. T. Ford, L. Sumner, W. Zhu, Y. H. Chang, P.-J. Um, K. H. Choi, P. A. Heiney and N. C. Maliszewskyj, New J. Chem., 1994, 18, 495;
28. (d) D. Lelièvre, L. Bosio, J. Simon, J.-J. André and F. Bensebaa, J. Am. Chem. Soc., 1992, 114, 4475;
29. (e) P. G. Schouten, J. F. van der Pol, J. W. Zwikker, W. Drenth and S. J. Picken, Mol. Cryst. Liq. Cryst., 1991, 195, 291; 1991, 208, 109;
30. (e) P. G. Schouten, J. F. van der Pol, J. W. Zwikker, W. Drenth and S. J. Picken, Mol. Cryst. Liq. Cryst., 1991, 195, 291; 1991, 208, 109;
31. (f) C. Sirlin, L. Bosio and J. Simon, J. Chem. Soc., Chem. Commun., 1988, 236;
32. (g) P. Weber, D. Guillon and A. Skoulios, J. Phys. Chem., 1987, 91, 2242.
33. (a) C. F. van Nostrum, A. W. Bosman, G. H. Gelinck, S. J. Picken, P. G. Schouten, J. M. Warman, A. J. Schouten and R. J. M. Nolte, J. Chem. Soc., Chem. Commun., 1993. 1120;
34. (b) C. F. van Nostrum, A. W. Bosman, G. H. Gelinck, P. G. Schouten, J. M. Warman, A. P. M. Kentgens, A. Meijerink, S. J. Picken, M. A. C. Devillers, U. Sohling, A.-J. Schouten and R. J. M. Nolte, Chem. Engl., 1995, 1, 171.
35. (a) B. Blanzat, C. Barthou, N. Tercier, J.-J. André and J. Simon, J. Am. Chem. Soc., 1987, 109, 135;
36. (b) G. Blasse, G. J. Dirksen, A. Meijerink, J. F. van der Pol, E. Neeleman and W. Drenth, Chem. Phys. Lett., 1989, 154, 420;
37. (c) D. Markovitsi, I. Lécuyer and J. Simon, J. Phys. Chem., 1991, 95, 3620.
38. (a) J. F. van der Pol, E. Neeleman, J. C. van Miltenburg, J. W. Zwikker, R. J. M. Nolte and W. Drenth, Macromolecules, 1990, 23, 155;
39. (b) J. F. van der Pol, J. W. Zwikker, J. M. Warman and M. P. de Haas, Recl. Trav. Chim. Pays-Bas, 1990, 109, 208;
40. (c) K. E. Treacher, G. J. Clarkson and N. B. McKeown, Liq. Cryst., 1995, 19, 887.
41. Z. Belarbi, C. Sirlin, J. Simon and J.-J. André, J. Phys. Chem., 1989, 93, 8105.
42. (a) P. G. Schouten, J. M. Warman, M. P. de Haas, J. F. van der Pol and J. W. Zwikker, J. Am. Chem. Soc., 1992, 114, 9028;
43. (b) P. G. Schouten, J. M. Warman, M. P. de Haas, M. A. Fox and H.-L. Pan, Nature, 1991, 353, 736;
44. (c) P. G. Schouten, J. M. Warman, M. P. de Haas, C. F. van Nostrum, G. H. Gelinck, R. J. M. Nolte, M. J. Copyn, J. W. Zwikker, M. K. Engel, M. Hanack and W. T. Ford, J. Am. Chem. Soc., 1994, 116, 6880;
45. (d) P. G. Schouten, J. M. Warman, G. H. Gelinck and M. J. Copyn, J. Phys. Chem., 1995, 99, 11 780.
46. V. Thanabal and V. Krishnan, J. Am. Chem. Soc., 1982, 104, 3643.
47. N. Kobayashi and T. Osa, Heterocycles, 1981, 15, 675.
48. R. Hendriks, O. E. Sielcken, W. Drenth and R. J. M. Nolte, J. Chem. Soc., Chem. Commun., 1986, 1464.
49. A. R. Koray, V. Ahsen and Ö. Bekâroglu, J. Chem. Soc., Chem. Commun., 1986, 932.
50. N. Kobayashi and Y. Nishiyama, J. Chem. Soc., Chem. Commun., 1986, 1462.
51. A. G. Gürek and Ö. Bekâroglu, Helv. Chim. Acta, 1994, 77, 1616.
52. (a) E. Musluoglu, V. Ahsen, A. Gül and Ö. Bekâroglu, Chem. Ber., 1991, 124, 2531;
53. (b) G. Gümüs, Z. Z. Öztürk, V. Ahsen, A. Gül and Ö. Bekâroglu, J. Chem. Soc., Dalton Trans., 1992, 2485;
54. (c) A. G. Gürek, V. Ahsen, A. Gül and Ö. Bekâroglu, J. Chem. Soc., Dalton Trans., 1991, 3367;
55. (d) M. Koçak, A. I. Okur and Ö. Bekâroglu, J. Chem. Soc., Dalton Trans., 1994, 323;
56. (e) E. Hamuryudan and Ö. Bekâroglu, J. Chem. Res. (S), 1993, 460.
57. (a) C. F. van Nostrum, F. B. G. Benneker, N. Veldman, A. L. Spek, A.-J. Schouten and R. J. M. Nolte, Recl. Trav. Chim. Pays-Bas, 1994, 113, 109;
58. (b) C. F. van Nostrum, F. B. G. Benneker, H. Brussaard, H. Kooijman, N. Veldman, A. L. Spek, J. Schoonman, M. C. Feiters and R. J. M. Nolte, Inorg. Chem., 1996, 35, 959.
59. J. W. Sibert, S. J. Lange, C. L. Stern, A. G. M. Barrett and B. M. Hoffman, Angew. Chem., 1995, 107, 2173; Angew. Chem., Int. Ed. Engl., 1995, 34, 2020.
60. J. W. Sibert, S. J. Lange, C. L. Stern, A. G. M. Barrett and B. M. Hoffman, Angew. Chem., 1995, 107, 2173; Angew. Chem., Int. Ed. Engl., 1995, 34, 2020.
61. O. E. Sielcken, M. M. van Tilborg, M. F. M. Roks, R. Hendriks, W. Drenth and R. J. M. Nolte, J. Am. Chem. Soc., 1987, 109, 4261.
62. (a) N. Kobayashi and A. B. P. Lever, J. Am. Chem. Soc., 1987, 109, 7433;
63. (b) V. Ahsen, E. Yilmazer, M. Ertas and Ö. Bekâroglu, J. Chem. Soc., Dalton Trans., 1988, 401.
64. O. E. Sielcken, H. C. A. van Lindert, W. Drenth, J. Schoonman, J. Schram and R. J. M. Nolte, Ber. Bunsenges, Phys. Chem., 1989, 93, 702.
65. O. E. Sielcken, W. Drenth and R. J. M. Nolte, Recl. Trav. Chim. Pays-Bas, 1990, 109, 425.
66. O. E. Sielcken, R. J. M. Nolte and J. Schoonman, Recl. Trav. Chim. Pays-Bas, 1990, 109, 230.
67. T. Toupance, V. Ahsen and J. Simon, J. Am. Chem. Soc., 1994, 116, 5352.
68. A. Gürek, V. Ahsen, A. Gül and Ö. Bekâroglu, J. Chem. Soc., Dalton Trans., 1991, 3367.
69. J. Simon, M. K. Engel and C. Soulié, New. Chem., 1992, 16, 287.
70. C. F. van Nostrum, S. J. Picken, A.-J. Schonten and R. J. M. Nolte, J. Am. Chem. Soc., 1995, 117, 9957.
71. O. E. Sielcken, L. A. van de Kuil, W. Drenth, J. Schoonman and R. J. M. Nolte, J. Am. Chem. Soc., 1990, 112, 3086.
72. High sensitivities have been reported. e.g. for unsubstituted lead phthalocyanines, but high operating temperatures (typically 150-200°C) are required and even then the response is usually very slow. It can take several hours to reach saturation level. See, for example, T. A. Jones and B. Bott, Sensors Actuators, 1984, 5, 43; A. Wilson and J. D. Wright, Mol. Cryst. Liq. Cryst., 1992, 211, 321.
73. High sensitivities have been reported. e.g. for unsubstituted lead phthalocyanines, but high operating temperatures (typically 150-200°C) are required and even then the response is usually very slow. It can take several hours to reach saturation level. See, for example, T. A. Jones and B. Bott, Sensors Actuators, 1984, 5, 43; A. Wilson and J. D. Wright, Mol. Cryst. Liq. Cryst., 1992, 211, 321.
74. P. Roisin, J. D. Wright, R. J. M. Nolte, O. E. Sielcken and S. C. Thorpe, J. Mater. Chem., 1992, 2, 131.
75. S. J. Peacock, V. Rivalle, J. D. Wright and H. C. Jaggers, in Sensors VI: Technology, Systems and Applications, ed. K. T. V. Grattan, Hilger, Bristol, 1993, p. 15.
76. A. Laschewsky, Adv. Mater., 1989, 1, 392.
77. N. B. McKeown, M. J. Cook, A. J. Thomson, K. J. Harrison, M. F. Daniel, R. M. Richardson and S. J. Roser, Thin Solid Films, 1988, 159, 469.
78. (a) G. C. Bryant, M. J. Cook, C. Ruggiero, T. G. Ryan, A. J. Thorne, S. D. Haslam and R. M. Richardson, Thin Solid Films, 1994, 243, 316;
79. (b) R. H. Poynter, M. J. Cook, M. A. Chesters, D. A. Slater, J. McMurdo and K. Welford, Thin Solid Films, 1994, 243, 346.
80. C. F. van Nostrum, P. T. J. H. ten Have, S. J. Picken, A. J. Schouten and R. J. M. Nolte, submitted for publication.
81. (a) T. Sauer, T. Arndt, D. N. Batchelder, A. A. Kalachev and G. Wegner, Thin Solid Films, 1990, 187, 357;
82. (b) C. F. van Nostrum, R. J. M. Nolte, M. A. C. Devillers, G. T. Oostergetel, M. N. Teerenstra and A. J. Schouten, Macromolecules, 1993, 26, 3306.
83. S. Schwiegk, T. Vahlenkamp, Y. Xu and G. Wegner, Macromolecules, 1992, 25, 2513.
84. M. L. Rodríguez-Méndez, J. Souto and J. A. de Saja, J. Raman Spectrosc., 1995, 26, 693.