Dithiacrown Ether Substituted Porphyrazines: Synthesis, Single-Crystal Structure, and Control of Aggregation in Solution by Complexation of Transition-Metal Ions

Inorganic Chemistry

Volumn 35, Issue 4, 1996, Pages 959-969

  Van Nostrum, Cornelus F ^a   Benneker, Franciscus B G ^a   Brussaard, Hugo ^a   Kooijman, Huub ^b   Veldman, Nora ^b   Spek, Anthony L ^b   Schoonman, Joop ^c   Feiters, Martinus C ^a   Nolte, Roeland J M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000992051     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic950704n     Document Type: Article

References (90)

1. Lehn, J.-M. Angew. Chem. 1988, 100, 91: Angew. Chem., Int. Ed. Engl. 1988, 27, 89.
2. Lehn, J.-M. Angew. Chem. 1988, 100, 91: Angew. Chem., Int. Ed. Engl. 1988, 27, 89.
3. Simon, J.; Engel, M. K.; Soulié, C. New J. Chem. 1992, 16, 287.
4. Toupance, T.; Ahsen, V.; Simon, J. J. Am. Chem. Soc. 1994, 116, 5352.
5. Leznoff, C. C ; Lever, A. B. P. Phthalocyanines, Properties and Applications: VCH: New York, 1989-1993; Vols 1-3.
6. (a) Thanabal, V ; Krishnan, V. J. Am. Chem. Soc. 1982, 104, 3643.
7. (b) Kobayashi, N.; Osa, T. Heterocycles 1981, 15, 675.
8. (a) Hendriks, R.; Sielcken, O. E.; Drenth, W.; Nolte, R. J. M. J. Chem. Soc., Chem. Commun. 1986, 1464.
9. (b) Koray, A R.; Ahsen, V.; Bekâroglu, Ö. J. Chem. Soc., Chem. Commun. 1986, 932.
10. (c) Kobayashi, N.; Nishiyama, Y. J. Chem. Soc., Chem. Commun. 1986, 1462.
11. (a) Sielcken, O. E.; van Tilborg, M. M.; Roks, M. F. M.; Hendriks, R.; Drenth, W.; Nolte, R. J. M. J. Am. Chem. Soc. 1987, 109, 4261.
12. (b) Kobayashi, N.; Lever, A. B. P. J. Am. Chem. Soc. 1987, 109, 7433.
13. (c) Ahsen, V ; Yilmazer, E.; Ertas, M.; Bekâroglu, Ö. J. Chem. Soc., Dalton Trans. 1988, 401.
14. Sielcken, O. E.; van Lindert, H. C. A.; Drenth, W.; Schoonman, J.; Schram, J.; Nolte, R. J. M. Ber. Bunsen-Ges. Phys. Chem. 1989, 93, 702.
15. (a) Sielcken, O. E.; Drenth, W.; Nolle, R. J. M. Recl. Trav. Chim. Pays-Bas 1990, 109, 425.
16. (b) Sielcken, O. E.; Nolte, R. J. M., Schoonman, J. Recl. Trav. Chim. Pays-Bas 1990, 109, 230.
17. (a) Roisin, P.; Wright, J. D.; Nolte, R. J. M.; Sielcken, O E.; Thorpe, S. C. J. Mater. Chem. 1992, 2, 131.
18. (b) Wright, J. D.; Roisin, P.; Rigby, G. P.; Nolte, R. J. M.; Cook, M. J.; Thorpe, S. C. Sens. Actuators, B 1993, 13, 276.
19. (c) Wright, J. D.; Roisin, P.; Rigby, G. P.; Erkizia, E ; Nolte, R. J. M.; Thorpe, S. C. Sens. Actuators, B 1993, 15-16, 301.
20. Peacock, S. J.; Rivalle, V.; Wright, J. D.; Jaggers, H. C. In Sensors VI: Technology, Systems and Applications; Grattan, K. T. V., Ed.; Hilger: Bristol, U K., 1993; pp 15-20.
21. (a) Musluoglu, E.; Ahsen, V.; Gül, A.; Bèkâroglu, Ö. Chem. Ber. 1991, 124, 2531.
22. (b) Gümüs, G.; Öztürk, Z. Z.; Ahsen, V.; Gül, A.; Bekâroglu, Ö. J. Chem. Soc., Dalton Trans. 1992, 2485.
23. (c) Gürek, A.; Ahsen, V., Gül, A.; Bekâroglu, Ö. J. Chem. Soc., Dalton Trans. 1991, 3367.
24. (d) Tan, N.; Gürek, A.; Bekârogiu, Ö.; Kadirgan, F. J. Electroanal. Chem. 1994, 374, 45.
25. (e) Koçak, M.; Okur, A I.; Bekâroglu, Ö. J. Chem. Soc., Dalton Trans. 1994, 323.
26. (f) Musluoglu, E.; Gürek, A.; Ahsen, V.; Gül, A.; Bekâroglu, Ö. Chem. Ber. 1992, 725, 2337
27. (g) Gürek, A. G.; Bekâroglu, Ö. Helv. Chim. Acta 1994, 77, 1616.
28. (a) Okur, A. I.; Gül, A.; Cihan, A.; Tan, N.; Bekâroglu, Ö. Synth. React. Inorg. Met.-Org. Chem. 1990, 20, 1399.
29. (b) Sarigül, S., Bekâroglu, Ö. Chem. Ber. 1989, 122, 291.
30. (c) Kobayashi, N.: Ohya, T.; Sato, M.; Nakajima, S.-I. Inorg. Chem. 1993, 32, 1803.
31. (a) Ahsen, V.; Yilmazer, E.; Gül, A.; Bekâroglu, Ö. Makromol. Chem Rapid Commun. 1987, 8, 243.
32. (b) Ahsen, V.; Yilmazer, E.; Bekâroglu, Ö. Makromol. Chem. 1988, 189, 2533.
33. (c) Musluoglu, E.; Öztürk, Z. Z.; Ahsen, V.; Gul, A.; Bekâroglu, Ö. J. Chem. Res. Synop. 1993, 6.
34. Sielcken, O. E.; van de Kuil, L. A.; Drenth, W.; Schoonman, J.; Nolte, R. J. M. J. Am. Chem. Soc. 1990, 112, 3086.
35. (a) van Nostrum, C. F.; Benneker, F. B. G.; Veldman, N.; Spek, A. L.; Nolte, R. J. M Recl. Trav. Chim. Pays-Bas 1994, 113, 109.
36. (b) van Nostrum, C. F. Thesis, University of Nijmegen, The Netherlands, 1995.
37. Sibert, J. W.; Lange, S. J.; Stern, C.; Hoffman, B. M.; Barrett, A. G. Abstracts of Papers; 206th National Meeting of the American Chemical Society, Chicago, IL, Sept 1993; American Chemical Society: Washington, DC, 1993; INOR 60.
38. Cooper, S. R.; Rawle, S. C Struct. Bonding 1990, 72, 1.
39. (a) Izatt, R. M.; Terry, R. E.; Hansen, L. D.; Avondet, A. G.; Bradshaw, J. S.; Dalley, N. K.; Jensen, T. E.; Christensen, J. J. Inorg. Chim. Acta. 1978, 30, 1.
40. (b) Lai, M.-T.; Shih, J.-S. Analyst 1986, 111, 891.
41. (c) Casabó, J.; Mestres, L.; Escriche, L.; Teixidor, P.; Pérez-Jiménez, C. J. Chem. Soc., Dalton Trans. 1991, 1969.
42. (d) Sato, M.; Kubo, M.; Ebine, S.; Akabori, S. Tetrahedron Lett 1982, 23, 185.
43. (e) Oue, M.; Akama, K., Kimura, K.; Tanaka, M.; Shono, T. J. Chem. Soc., Perkin Trans. I 1989, 1675.
44. (f) Brzozka, Z.; Cobben, P. L. H. M.; Reinhoudt, D. N.; Edema, J. J. H.; Buter, J.; Kellogg, R. M. Anal. Chim. Acta 1993, 273, 139.
45. (g) Takeshita, H.; Yin, B. Z.; Kubo, K.; Mori, A. Bull. Chem. Soc. Jpn. 1993, 66, 3451.
46. Holdt, H.-J.; Teller, J. Z. Chem. 1988, 28, 249.
47. Märkl, G.; Vybiral, R. Tetrahedron Lett. 1989, 30, 2903.
48. Sibert, J. W.; Lange, S. J.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. Inorg. Chem. 1995, 34, 2300.
49. Holdt, H.-J. Pure Appl. Chem. 1993, 65, 477.
50. Sibert, J. W.; Lange, S. J.; Stern, C.; Hoffman, B. M.; Barrett, A. G. M. J. Chem. Soc., Chem. Commun. 1994, 1751.
51. Davison, A.; Holm, R. H. Inorg. Synth. 1967, 6, 8.
52. Pedersen, C. J. J. Org. Chem. 1972, 52, 66.
53. MacDonald, J. R.; Schoonman, J.; Lehnen, A. P J. Electroanal. Chem. 1982, 131, 77.
54. de Boer, J. L.; Duisenberg, A. J. M. Acta Crystallogr. 1984, A40, C410.
55. Spek, A. L. J. Appl. Crystallogr. 1988, 21, 578.
56. Walker, N.; Stuart, D. Acta Crystallogr. 1983, A39, 158.
57. Altomare, A.; Cascarano, G ; Giacovazzo, C.; Guagliardi, A. J. Appl. Crystallogr. 1993, 26, 343.
58. Sheldrick, G. M.; SHELXL-93 Program for crystal structure refinement, University of Göttingen, Germany, 1993
59. Spek, A. L. Acta Crystallogr. 1990, A46, C34.
60. Wilson, A. J. C., Ed. International Tables for Crystallography; Volume C, Kluwer Academic Publishers: Dordrecht, The Netherlands, 1992.
61. Sheldrick, G. M. SHELXS86 Program for crystal structure determination. University of Göttingen, Germany, 1986
62. Sheldrick, G. M. SHELX76 Program for crystal structure determination. University of Cambridge, England, 1976.
63. Cromer, D. T.; Mann, J. B. Acta Crystallogr. 1968, A24, 321.
64. Cromer, D. T.; Liberman, D. J. Chem. Phys. 1970, 53, 1891.
65. Schramm, C. J.; Hofmann, B. M. Inorg. Chem. 1980, 19, 383.
66. Lelj, F.; Morelli, G.; Ricciardi, G.; Roviello, A.; Sirigu, A. Liq. Cryst. 1992, 12, 941.
67. Hartung, H.; Ahnert, R.; Schollmeyer, D.; Holdt, H.-J.; Teller, J J. Prakt. Chem. 1992, 334, 155.
68. Wolf, R. E.; Hartmann, J. R.; Storey, J. M. E.; Foxman, B. M.; Cooper, S. R. J. Am Chem. Soc 1987, 109, 4328.
69. Chow, H.-C.; Serlin, R.; Strouse, C. E. J. Am. Chem. Soc. 1975, 97, 7230.
70. (a) Agostiano, A.; Cosma, P.: Della Monica, M. J. Photochem Photobiol. A: Chem. 1991, 58, 201.
71. (b) Agostiano, A.; Della Monica, M.; Palazzo, G.; Trotta, M. Biophys. Chem. 1993, 47, 193.
72. Kobayashi, N. In ref 4, Vol. 2, pp 97-161.
73. (a) Velázquez, C. S.; Fox, G. A , Broderick, W. E.; Andersen, K A.; Anderson, O. P.; Barrett, A. G. M.; Hoffman, B. M. J. Am. Chem. Soc. 1992, 114, 7416.
74. (b) Shaposhnikov, G. P.; Kulinich, V. P.; Osipov, Y. M.; Smirnov, R. P. Chem. Heterocycl. Compd. 1986, 1036
75. Doppelt, P ; Huille, S. New J. Chem. 1990, 14, 607.
76. Weiss, C.; Kobayashi, H.; Gouterman, M J. Mol. Spectrosc. 1965, 6, 415.
77. Pezeshk, A ; Pasenkiewicz-Gierula, M.; Subczynski, W. K.; Antholine, W. E. J. Phys. Chem. 1990, 94, 451
78. Chikira, M.; Kon, H.; Hawley, R. A.; Smith, K. M. J. Chem. Soc., Dalton Trans. 1979, 246.
79. (a) Öztürk, Z. Z.; Musluoglu, E.; Ahsen, V.; Gül, A.; Bekâroglu, Ö. J. Mater. Sci. 1992, 27, 6183.
80. (b) Öztürk, Z. Z.; Altindal, A.; Gürek, A.; Bekâroglu, Ö. Synth. Metals 1992, 52, 291.
81. (a) Heilmeier, G. H.; Harrison, S. E. Phys. Rev. 1963, 132, 2010.
82. (b) Nalwa, H. S. J. Electron. Mater. 1988, 17, 291.
83. (c) van der Pol, J. F. Thesis, 1990. University of Utrecht, The Netherlands.
84. Belarbi, Z., Maitrot, M.; Ohta, K.; Simon, J.; André, J. J.; Petit, P. Chem. Phys. Lett. 1988, 143, 400.
85. Belarbi, Z.; Sirlin, C.; Simon, J.; André, J. J. J. Phys. Chem. 1989, 93, 8105.
86. 16a we concluded that MPz(15) remains monomeric and that MPz(18) dimerizes in the presence of 6 equiv of silver perchlorate. On the basis of the results presented in this paper, we have to withdraw these conclusions.
87. Hall Griffith, E. A.; Amma, E. L. J. Am. Chem. Soc. 1974, 96, 743.
88. + ion is probably fully surrounded by a single crown ether ring in solution (see ref 22).
89. (a) Kasha, M.; Rawls, H. R.; Ashraf El-Bayoumi, M. Pure Appl. Chem. 1965, 11, 371.
90. (b) Rae, E. G.; Kasha, M. In Physical Processes in Radiation Biology; Augenstein, L.; Mason, R.; Rosenberg, B., Eds.; Academic Press: New York, 1964.