Synthesis and Characterization of Metallo and Metal-Free Octaalkylphthalocyanines and Uranyl Decaalkylsuperphthalocyanines

Inorganic Chemistry

Volumn 20, Issue 11, 1981, Pages 3766-3770

  Cuellar, Edward A ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000088651     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic50225a039     Document Type: Article

References (98)

1. The rigorous Chemical Abstracts nomenclature for uranyl superphthalocyanine is [[7, 12:21, 26-diimino-19, 14:28, 33:35, 5-trinitrilo-5H-pentabenzo[c, h, m, r, w] [1, 6, 11, 16, 21] pentaazacyclopentacosinato]-(2-)]dioxouranium(VI).
2. Kasuga, K.; Tsutsui, M. Coord. Chem. Rev. 1980, 32, 67.
3. Boucher, L. J. In “Coordination Chemistry of Macrocyclic Compounds”; Melson, G. A., Ed., Plenum Press: New York, 1979; pp 461-516.
4. Meltzer, Y. L. “Phthalocyanine Technology”, Chemical Process Review No. 42; Noyes Data Corp.: Park Ridge, NJ, 1970.
5. Lever, A. B. P. Adv. Inorg. Chem. Radiochem. 1965, 7, 27.
6. Moser, F. H.; Thomas, A. L. “Phthalocyanine Compounds”; Reinhold: New York, 1963.
7. Martens, C. R. In “Riegel’s Handbook of Industrial Chemistry”, 7th ed.; Kent, J. A., Ed.; Van Nostrand-Reinhold: New York, 1974; Chapter 22.
8. Payne, H. F. “Organic Coating Technology”; Wiley: New York, 1961; Vol. II, pp 896-899.
9. Harbour, J. R.; Tromp, J.; Hair, M. L. J. Am. Chem. Soc. 1980, 102, 1874.
10. Shirai, H.; Maruyama, A.; Takano, J.; Kobayashi, K.; Hojo, N.; Urushido, K. Makromol. Chem. 1980, 181, 565.
11. Shirai, H.; Maruyama, A.; Kobayashi, K.; Hojo, N.; Urushido, K. Makromol. Chem. 1980, 181, 575.
12. Schutten, J. H.; Zwart, J. J. Mol. Catal. 1979, 5, 109.
13. Inoue, H.; Nagata, T.; Hata, H.; Imoto, E. Bull. Chem. Soc. Jpn. 1979, 52, 469.
14. Steinbach, F.; Zobel H. Z. Phys. Chem. (Wiesbaden) 1978, 111, 113.
15. Steinbach, F.; Joswig, H.-J. J. Catal. 1978, 55, 272 and references cited therein
16. Mochida, I.; Takeyoshi, K.; Fujitsu, H.; Takeshita, K. J. Mol. Catal. 1978, 3, 417.
17. Manassen, J. Catal. Rev. 1974, 9, 223.
18. Zagal, J. H. J. Electroanal. Chem. 1980, 109, 389.
19. Kilcuchi, T.; Sasaki, H.; Toshima, S. Chem. Lett. 1980, 5.
20. Van Veen, J. A. R.; Visser, C. Electrochim. Acta 1979, 24, 921.
21. Kobayashi, N.; Fujihira, M.; Sunakawa, K. J. Electroanal. Chem. 1979, 101, 269.
22. Maroie, S.; Savy, M.; Verbist, J. J. Inorg. Chem. 1979, 18, 2560.
23. Zagal, J.; Sen, R. K.; Yeager, E. J. Electroanal. Chem. 1977, 83, 207 and references cited therein.
24. Ahuja, R. C.; Hauffe, K. Ber, Bunsenges. Phys. Chem. 1980, 84, 68 and references cited therein
25. Ahuja, R. C.; Hauffe, K. Ber, Bunsenges. Phys. Chem. 1980, 84, 138.
26. Giraudeau, A.; Fan, F.-R. F.; Bard, A. J. J. Am. Chem. Soc. 1980, 102, 5137.
27. Minami, N. J. Chem. Phys. 1980, 72, 6317.
28. Jaeger, C. D.; Fan, F.-R. F.; Bard, A. J. J. Am. Chem. Soc. 1980, 102, 2592.
29. Langford, C. H.; Hollebone, B. R.; Vandemoot, T. Adv. Chem. Ser. 1980 No. 184, 139.
30. Minami, N. Ber. Bunsenges. Phys. Chem. 1979, 83, 476 and references cited therein
31. Fan, F.-R. F.; Bard, A. J. J. Am. Chem. Soc. 1979, 101, 6139.
32. Uchida, K.; Soma, M.; Onishi, T.; Tamaura, K. Z. Phys. Chem. (Wiesbaden) 1978, 106, 317.
33. Shepard, V. R., Jr.; Armstrong, N. R. J. Phys. Chem. 1979, 83, 1268.
34. Fan, F.-R.; Faulkner, L. R. J. Am. Chem. Soc. 1979, 101, 4779.
35. Tachikawa, H.; Faulkner, L. R. J. Am. Chem. Soc. 1978, 100, 4379 and references cited therein.
36. Dahlberg, S. C.; Musser, M. E. J. Chem. Phys. 1980, 72, 6706.
37. Isett, L. C. Appl. Phys. Lett. 1980, 36, 376.
38. Dahlberg, S. C.; Musser, M. E. J. Chem. Phys. 1979, 70, 5021 and references cited therein
39. Loutfy, R. O.; Sharp, J. H. J. Chem. Phys. 1979, 71, 1211 and references cited therein
40. Fan, F.-R.; Faulkner, L. R. J. Chem. Phys. 1978, 69, 3334 and references cited therein
41. Fan, F.-R.; Faulkner, L. R. J. Chem. Phys. 1978, 69, 3341.
42. Loutfy, R. D.; Menzel, E. R. J. Am. Chem. Soc. 1980, 102, 4967.
43. Dolphin, D.; James, B. R.; Murray, A. J.; Thornback, J. R. Can. J. Chem. 1980, 58, 1125.
44. Lever, A. B. P.; Wilshire, J. P. Inorg. Chem. 1978, 17, 1145.
45. Przywarska-Boniecka, H.; Trynda, L.; Antonini, E. Eur. J. Biochem. 1975, 52, 567.
46. Stynes, D. V. J. Am. Chem. Soc. 1974, 96, 5942.
47. Lever, A. B. P.; Wilshire, J. P.; Quan, S. K. J. Am. Chem. Soc. 1979, 101, 3668.
48. Eckert, H.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1976, 15, 681.
49. Prochäzka, M.; Smolkovä-Keulemansovä, E. J. Chromatogr. 1980, 189, 25.
50. Marks, T. J.; Kalina, D. W. In “Extended Linear Chain Compounds”: Miller, J. S., Ed.; Plenum Press: New York, in press
51. Marks, T. J. Ann. N.Y. Acad. Sci. 1978, 313, 594.
52. Dahlberg, S. C.; Musser, M. E. Surf. Sci. 1979, 90, 1.
53. Orr, W. A. Dahlberg, S. C. J. Am. Chem. Soc. 1979, 101, 2875.
54. Petersen, J. L.; Schramm, C. J.; Stojakovic, D. R.; Hoffman, B. M.; Marks, T. J. J. Am. Chem. Soc. 1977, 99, 286.
55. Schramm, C. J.; Stojakovic, D. R.; Hoffman, B. M.; Marks, T. J. Science 1978, 200, 47.
56. Scaringe, R. P.; Schramm, C. J.; Stojakovic, D. R.; Hoffman, B. M.; Ibers, J. A.; Marks, T. J. J. Am. Chem. Soc. 1980, 102, 6702.
57. Schoch, K. F., Jr.; Kundalkar, B. R.; Marks, T. J. J. Am. Chem. Soc. 1979, 101, 7071.
58. Marks, T. J.; Schoch, K. F., Jr.; Kundalkar, B. R. Synth. Met. 1979/1980, 1, 337.
59. Dirk, C. W.; Lyding, J. W.; Schoch, K. F., Jr.; Kannewurf, C. R.; Marks, T. J. Org. Coat. Plast. Chem. 1980, 43, 646.
60. Dirk, C. W.; Mintz, E. A.; Schoch, K. F., Jr.; Marks, T. J. J. Macromol. Sci.–Chem. 1981, A16, 275.
61. Lindoy, L. F. Chem. Soc. Rev. 1975, 4, 421.
62. Christensen, J. J.; Eatough, D. J.; Izatt, R. M. Chem. Rev. 1974, 74, 351.
63. Black, D.S.T.C.; Hartshorn, A. J. Coord. Chem. Rev. 1973, 9, 219.
64. Busch, D. H.; Farmery, K.; Katovic, V.; Melnyk, A. C.; Sperati, C. D.; Tokel, N. E. Adv. Chem. Ser. 1971, No. 100, 44.
65. Lindoy, L. F.; Busch, D. H. Prep. Inorg. React. 1971, 6, 1.
66. Curtis, N. F. Coord. Chem. Rev. 1968, 3, 3.
67. Busch, D. H. Helv. Chim. Acta, Fase. Extraordinarias, 1967, Alfred Werner Commemoration Volume.
68. Day, V. W.; Marks, T. J.; Wachter, W. A. J. Am. Chem. Soc. 1975, 97, 4519.
69. Marks, T. J.; Stojakovic, D. R. J. Am. Chem. Soc. 1978, 100, 1695.
70. Marks, T. J.; Stojakovic, D. R. J. Chem. Soc., Chem. Commun. 1975, 28.
71. Cuellar, E. A.; Stojakovic, D. R.; Marks, T. J. Inorg. Synth. 1980, 20, 97.
72. Preliminary communication: Symposium on the Structure and Properties of Highly Conducting Polymers and Graphite, San Jose, CA, March 29-30, 1979.
73. Leary, J. A.; Suttle, J. F. Inorg. Synth. 1957, J. 148. U02C12 [Gallard-Schlesinger Chem. Corp., Carle Place, NY 11514; “minimum assay (ex U) 90%”] has been used successfully. We caution, though, that variable amounts of water present in most commercial U02C12 may affect the reproducibility of this procedure.
74. Shriver, D. F. “The Manipulation of Air-Sensitive Compounds”; McGraw-Hill: New York, 1969.
75. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
76. Dolphin, D.; Sams, J. R.; Tsin, T. B. Inorg. Synth. 1980, 20, 155.
77. Barrett, P. A.; Frye, D. A.; Linstead, R. P. J. Chem. Soc. 1938, 1157.
78. Barrett, P. A.; Dent, C. E.; Linstead, R. P. J. Chem. Soc. 1936, 1719.
79. Klingsberg, E. Synthesis 1972, 3, 29.
80. Prepared from 4, 5-dibromo-1, 2-dimethylbenzene30 [by using the procedure of: Kovshev, E. L.; Solov’eva, L. I.; Mikhalenko, S. A.; Luk’-yanets, E. A. Zh. Vses, Khim. Ova. 1976, 21, 465] but modified as in section B of the Experimental Section.
81. Kalina, D. W. Ph.D. Dissertation, Northwestern University, Evanston, IL, 1979.
82. Prepared from 100% C6D6 (Aldrich Chemical Co.) and chlorine gas. See: Lowensheim, F. A.; Moran, M. K. “Faith, Keyes, and Clark’s Industrial Chemicals”, 4th ed.; Wiley-Interscience: New York, 1975; pp 258-260.
83. Mikhalenko, S. A.; Yagodina, L. A.; Luk’yanets, E. A. J. Gen. Chem. USSR (Engl. Transl.) 1976, 46, 1557.
84. Pawlowski, G.; Hanack, M. Synthesis 1980, II, 287.
85. Pawlowski, G.; Hanack, M. Synth. Commun. 1981, 11, 351.
86. Gouterman, M. In “The Porphyrins”; Dolphin, D., Ed, ; Academic Press: New York, 1978; Vol. 3, Part A. pp 1-163.
87. Schaffer, A. M., Gouterman, M.; Davidson, E. R. Theor. Chim. Acta 1973, 30, 9.
88. Schaffer, A. M.; Gouterman, M. Theor. Chim. Acta. 1972, 25, 62.
89. Edwards, L.; Gouterman, M. J. Mol. Spectrosc. 1970, 33, 292.
90. Chen, I. J. Mol. Spectrosc. 1967, 23, 131.
91. Case, D. A.; Karplus, M. J. Am. Chem. Soc. 1977, 99, 6182.
92. Stillman, M. J.; Thompson, A. J. J. Chem. Soc., Faraday Trans. 2 1974, 70, 790, 805.
93. Chantrell, S. J.; McAuliffe, C. A.; Munn, R. W.; Pratt, A. C. Coord. Chem. Rev. 1975, 16, 259 and references cited therein
94. Hochstrasser, R. M.; Marzzacco, C. J. Chem. Phys. 1968, 49, 971.
95. Gouterman, M. J. Mot. Spectrosc. 1961, 6, 138.
96. Mikhalenko, S. A.; Barkanova, S. V.; Lebedev. O. L.; Luk’yanets, E. A. J. Gen. Chem. USSR (Engl. Transl.) 1971, 41, 2770.
97. Whalley, M. J. Chem. Soc. 1961, 866.
98. Prepared by Stojakovic, D. R. Ph.D. Dissertation, Northwestern Unversity, Evanston, IL, 1977. See ref 23a for ligand synthes