Tetrakis(thiadiazole)porphyrazines. 1. Syntheses and Properties of Tetrakis(thiadiazole)porphyrazine and Its Magnesium and Copper Derivatives

Inorganic Chemistry

Volumn 37, Issue 7, 1998, Pages 1533-1539

  Stuzhin, P A ^a,b   Bauer, E M ^a   Ercolani, C ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b IVANOVO STATE UNIVERSITY OF CHEMISTRY AND TECHNOLOGY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001622464     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9609259     Document Type: Article

References (56)

1. (a) Ercolani, C.; Paoletti, A. M.; Pennesi, G.; Rossi, G.; Chiesi-Villa, A.; Rizzoli, C. J. Chem. Soc., Dalton Trans. 1990, 1971.
2. 2-; DMN = diaminomaleonitrile; ClNP = 1-chloronaphthalene; PhCl = chlorobenzene.
3. Paoletti, A. M.; Pennesi, G.; Rossi, G.; Ercolani, C. Inorg. Chem. 1995, 34, 4780.
4. (a) Capobianchi, A.; Paoletti, A. M.; Pennesi, G.; Rossi, G.; Caminiti, R.; Ercolani, C. Inorg. Chem. 1994, 33, 4635.
5. (b) Capobianchi, A.; Pennesi, G.; Rossi, G.; Paoletti, A. M.; Caminiti, R.; Sadun, C.; Ercolani, C. Inorg. Chem. 1996, 35, 4643.
6. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
7. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
8. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
9. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
10. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
11. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
12. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
13. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
14. Recent reviews on the synthesis and properties of porphyrazine systems: (a) Kobayashi, N. In Phthalocyanines-Properties and Applications; Leznoff, C. C. Lever, A. B. P., Eds.; VCH Publishers; New York, 1993; Vol. 2. (b) Stuzhin, P. A.; Khelevina, O. G. Coord. Chem. Rev. 1996, 147, 41. Stuzhin, P. A.; Khelevina, O. G.; Berezin, B. D. In Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1996; Vol. 4, and references therein. See also: (d) Fitzgerald, J.; Owen, H. Synthesis 1991, 686. (e) Fitzgerald, J. P.; Haggerty, B. S.; Rheingold, A. L.; May, L.; Brewer, G. A. Inorg. Chem. 1992, 31, 2006. (f) Ni, Y.; Fitzgerald, J. P.; Carroll. P.; Wayland, B. B. Inorg. Chem. 1994, 33, 2029. (g) Stuzhin, P. A.; Migalova, I. S.; Berezin, B. D.; Lyubimov, A. V. Koord. Khim. 1994, 20, 444, (h) Stuzhin, P. A.; Hamdush, M.; Ziener, U. Inorg. Chim. Acta 1995, 236, 131. Eichorn, D. M.; Yang, S.; Jarrell, W.; Baumann, T. F.; Beall, L. S.; White, A. J. P.; Williams, D. J.; Barrett, G. M.; Huffman B. M. J. Chem. Soc., Chem. Commun. 1995, 1703.
15. (a) The Phthalocyanines; Moser, F. H., Thomas, A. L., Eds.; CRC Press: Boca Raton, FL, 1983; Vols. I and II.
16. (b) Phthalocyanines - Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1993-1996; Vols. 1-4.
17. The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vols. I-VII.
18. (a) Schultz, H.; Lehmann, H.; Rein, M.; Hanack, M. Struct. Bonding 1991, 74, 41.
19. (b) Hanack, M.; Lang, M. Adv. Mater. 1994, 6, 819.
20. (c) See refs 1-3.
21. Mørkved, E. H.; Neset, S. M.; Kjøsen, H.; Hvistendahl, G.; Mo, F. Acta Chem. Scand. 1994, 48, 912.
22. Ribaldone, G.; Grecu R. German Pat. 2651604, 1977. (Chem. Abstr. 1977, 87, 135344).
23. Ribaldone, G.; Grecu R. German Pat. 2651604, 1977. (Chem. Abstr. 1977, 87, 135344).
24. Figgis, B. N.; Lewis, J. In Modern Coordination Chemistry; Lewis, J., Wilkins, R. G., Eds.; Intel-science: New York, I960; Chapter 6.
25. Fischer, M. S.; Templeton, D. H.; Zalkin, A.; Calvin, M. J. Am. Chem. Soc. 1971, 93, 2622.
26. Sammes, M. P. J. Chem. Soc., Perkin Trans. 2 1972, 160.
27. Gurinovich, G. P.; Sevchenko, A. N.; Solovyov, K. N. Spectroscopy of Gurinovich, and Related Compounds; Nauka i Technika: Minsk, Russia, 1968.
28. (a) Stuzhin, P. A.; Khelevina, O. G.; Ryabova, M. N.; Berezin, B. D. Zh. Prtkl. Spektrosk, 1990, 52, 94.
29. (b) See ref 4a, p 104.
30. Solovyov, K. N.; Gladkov, L. L., Starukhin, A. S.; Shkirman, S. F. Spectroscopy of Porphyrins: Vibronic States: Nauka i Tekhnika: Minsk. Russia, 1985.
31. (a) Gouterman, M. In ref 6, Vol. III and references therein.
32. (b) Kuzmitski, V. A.; Solov'yov, K. N.; Tsvirko, M. P. In Porphyrins: Spectroscopy, Electrochemistry and Application: Enikolopyan, N. S., Ed.; Nauka: Moscow, 1987; p 37.
33. (c) Stillman, M. J.; Nyokong, T. In ref 5b, Vol. 1, p 133.
34. Dvornikov, S. S.; Knyukshto, V. N.; Kuzmitski V. A.; Shul'ga, A. M.; Solovyov, K. N. J. Lumin, 1981, 23, 373.
35. (a) Gal'pern, M. G.; Luk'yanets, E. A. Zh. Obshch. Khim. 1969, 39, 2536.
36. (b) Gal'pern, E. G.; Luk'yanets, E. A.; Gal'pern, M. G. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 1776.
37. (a) Strelkova, T. I.; Gurinovich, G. P. Zh. Prikl. Spekrrosk. 1967, 9, 882.
38. (b) Khelevina, O. G.; Stuzhin, P. A.; Glazunov, A. V.; Berezin, B. D. Khim. Geterotsikl. Soedin. 1987, 629.
39. Berezin, B. D.; Stuzhin, P. A.; Khelevina, O. G. Khim. Geterotsikl. Soedin. 1986, 1677.
40. (a) Gaspard, S.; Verdaguer, M.; Viovy, R. J. Chem. Res., Miniprint 1979, 3072.
41. (b) Akopov, A. S.; Bykova, V. V.; Berezin, B. D. Koord. Khim. 1981, 7, 1332.
42. (c) Akopov, A. S.; Bykova, V. V.; Berezin, B. D. Zh. Org. Khim. 1981, 17, 1027.
43. (d) Berezin, B. D.; Klyuev, V. N.; Korzhenevskii, A. B. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 1977, 20, 619.
44. Weinstock, L. M.; Pollak, P. I. Adv. in Heterocycl. Chem. 1968, 9, 107.
45. (a) Whalley, M. J. Chem. Soc. 1961, 866.
46. (b) Berezin, B. D.; Khelevina, O. G.; Gerasimova, N. D.; Stuzhin, P. A. Zh. Fiz. Khim. 1982, 56, 2768.
47. (c) Khelevina: O. G.; Chizhova, N. V.; Bertvin, B. D. Koord. Khim. 1991, 17, 400.
48. (d) Petrov, O. A.; Khelevina, O. G. Zh. Fiz. Khim. 1996, 70, 775.
49. Ledson, D. L.; Twigg, M. V. Inorg. Chim. Acta 1975, 13, 43.
50. (a) Gyul'maev, A. M.; Stankevich I. V.; Todres, Z. V. Khim. Geterotsikl. Soedin. 1973, 1473.
51. (b) Palmer, M. H.; Findley, R. H.; Ridyard, J. N. A.; Barry, A.; Swift, D. J. Mol. Struct. 1977, 39, 189.
52. (c) Bhattacharyya, A.; Bhattacharyya, A. A. Indian. J. Chem. 1983, B22, 802.
53. (a) Luzzati, V. Acta Crystallogr. 1951, 4, 193.
54. (b) Stiefvater, O. L. Z. Naturforsch. 1978, 33A, 1511.
55. (c) Gieren, A.; Betz, H.; Hübner, T.; Lamm, V.; Neidlein, R.; Droste, D. Z. Naturfarsch. 1984, 39B, 485.
56. Hyperchem: A molecular modeling system. Release 3.0; Hypercube and Autodesk: 1993.