meso-porphyrinylphosphine oxides: Mono- and bidentate ligands for supramolecular chemistry and the crystal structures of monomeric {[10,20-diphenylporphyrinatonickel(II)-5,15-diyl]-bis-[P(O)Ph2] and polymeric self-coordinated {[10,20-diphenylporphyrinatozinc(II)-5,15-diyl]-bis- [P(O)Ph2]}

Inorganic Chemistry

Volumn 45, Issue 16, 2006, Pages 6479-6489

  Atefi, Farzad ^a   McMurtrie, John C ^a   Turner, Peter ^b   Duriska, Martin ^c   Arnold, Dennis P ^a  

^a QUEENSLAND UNIVERSITY OF TECHNOLOGY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; ORGANOMETALLIC COMPOUND; OXIDE; PHOSPHINE DERIVATIVE; POLYMER; PORPHYRIN;

ARTICLE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; LIGANDS; ORGANOMETALLIC COMPOUNDS; OXIDES; PHOSPHINES; POLYMERS; PORPHYRINS;

EID: 33748368528     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic060372u     Document Type: Article

References (79)

1. (a) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000; Vol. 1-10.
2. (b) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2004; Vol. 11-20.
3. Vicente, M. G. H. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 1, pp 149-199.
4. Hyslop, A. G.; Kellett, M. A.; Iovine, P. M.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676-12677.
5. Hata, H.; Shinokubo, H.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 8264-8265.
6. Smith, K. M.; Langry, K. C. J. Chem. Soc., Chem. Commun. 1980, 217-218.
7. Kato, A.; Arnold, D. P.; Miyasaka, H.; Yamashita, M.; Sugiura, K.-i. unpublished results.
8. Smith, K. M.; Barnett, G. H.; Evans, B.; Martynenko, Z. J. Am. Chem. Soc. 1979, 101, 5953-5961.
9. Sugiura, K.-i.; Matsumoto, T.; Ohkouchi, S.; Naitoh, Y.; Kawai, T.; Takai, Y.; Ushiroda, K.; Sakata, Y. J. Chem. Soc., Chem. Commun. 1999, 1957-1958.
10. (a) Arnold, D. P.; Sakata, Y.; Sugiura, K.-i.; Worthington, E. I. J. Chem. Soc., Chem. Commun. 1998, 2331-2332.
11. (b) Arnold, D. P.; Healy, P. C.; Hodgson, M. J.; Williams, M. L. J. Organomet. Chem. 2000, 607; 41-50.
12. (c) Hodgson, M. J.; Healy, P. C.; Williams, M. L.; Arnold, D. P. J. Chem. Soc., Dalton Trans. 2002, 4497-4504.
13. (d) Hartnell, R. D.; Arnold, D. P. Organometallics 2004, 23, 391-399.
14. (e) Hartnell, R. D.; Arnold, D. P. Eur. J. Inorg. Chem. 2004, 1262-1269.
15. (f) Hartnell, R. D.; Edwards, A. J.; Arnold, D. P. J. Porphyrins Phthalocyanines 2002, 6, 695-707.
16. See For example: (a) Karayannis, N. M.; Mikulski, C. M.; Pytlewski, L. L. Inorg. Chim. Acta, Rev. 1971, 5, 69-105.
17. (b) Sterenberg, B. T.; Scoles, L.; Carty, A. J. Coord. Chem. Rev. 2002, 231, 183-197.
18. Arnaud-Neu, F.; Browne, J. K.; Byrne, D.; Marrs, D. J.; McKervey, M. A.; O'Hagan, P.; Schwing-Weill, M. J.; Walker, A. Chem. - Eur. J. 1999, 5, 175-186.
19. Märkl, G.; Gschwendner, K.; Roetzer, I.; Kreitmeier, P. Helv. Chim. Acta 2004, 87, 825-844.
20. Yashunsky, D. V.; Ponomarev, G. V.; Arnold, D. P. Tetrahedron Lett. 1996, 37, 7147-7150.
21. Sawamura, M.; Nakamura, E. In 74th Annual Meeting of the Chemical Society of Japan; Chemical Society of Japan: Kyoto, 1998; p 4A315.
22. Märkl, G.; Reiss, M.; Kreitmeier, P.; Noeth, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2230-2234.
23. (a) Darling, S. L.; Stulz, E.; Feeder, N.; Bampos, N.; Sanders, J. K. M. New J. Chem. 2000, 24, 261-264.
24. (b) Stulz, E.; Ng, Y.-F.; Scott, S. M.; Sanders, J. K. M. J. Chem. Soc., Chem. Commun. 2002, 524-525.
25. (c) Stulz, E.; Maue, M.; Feeder, N.; Teat Simon, J.; Ng, Y.-F.; Bond Andrew, D.; Darling Scott, L.; Sanders, J. K. M. Inorg. Chem. 2002, 41, 5255-5268.
26. (d) Stulz, E.; Sanders, J. K. M.; Montalti, M.; Prodi, L.; Zaccheroni, N.; Fabrizi de Biani, F.; Grigiotti, E.; Zanello, P. Inorg. Chem. 2002, 41, 5269-5275.
27. (e) Stulz, E.; Scott, S. M.; Ng, Y.-F.; Bond, A. D.; Teat, S. J.; Darling, S. L.; Feeder, N.; Sanders, J. K. M. Inorg. Chem. 2003, 42, 6564-6574.
28. (f) Stulz, E.; Scott, S. M.; Bond, A. D.; Otto, S.; Sanders, J. K. M. Inorg. Chem. 2003, 42, 3086-3096.
29. (g) Stulz, E.; Maue, M.; Scott, S. M.; Mann, B. E.; Sanders, J. K. M. New J. Chem. 2004, 28, 1066-1072.
30. Saito, M.; Nishibayashi, Y.; Uemura, S. Organometallics 2004, 23, 4012-4017.
31. Slagt, V. F.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Angew. Chem., Int. Ed. 2003, 42, 5619-5623.
32. De la Torre, G.; Gouloumis, A.; Vazquez, P.; Torres, T. Angew. Chem., Int. Ed. 2001, 40, 2895-2898.
33. Shine, H. J.; Padilla, A. G.; Wu, S.-M. J. Org. Chem. 1979, 44, 4069-4075.
34. (a) Ruhlmann, L.; Giraudeau, A. J. Chem. Soc., Chem. Commun. 1996, 2007-2008.
35. (b) Ruhlmann, L.; Giraudeau, A. Eur. J. Inorg. Chem. 2001, 659-668.
36. (c) Ruhlmann, L.; Gross, M.; Giraudeau, A. Chem. - Eur. J. 2003, 9, 5085-5096.
37. Engel, R. In Handbook of Organophosphorus Chemistry; Engel, R., Ed.; M. Dekker: New York, 1992; pp 193-239.
38. Burrell, A. K.; Officer, D. L.; Plieger, P. G.; Reid, D. C. W. Chem. Rev. 2001, 101, 2751-2796.
39. (a) Kim, S.-W.; Kim, S.; Tracy, J. B.; Jasanoff, A.; Bawendi, M. G. J. Am. Chem. Soc. 2005, 127, 4556-4557.
40. (b) Spichal, Z.; Necas, M.; Pinkas, J. Inorg. Chem. 2005, 44, 2074-2080.
41. Shriver, D. F.; Drezdzon, M. A. The manipulation of air-sensitive compounds; Wiley: New York, 1986.
42. Laha, J. K.; Dhanalekshmi, S.; Taniguchi, M.; Ambroise, A.; Lindsey, J. S. Org. Process Res. Dev. 2003, 7, 799-812.
43. Shanmugathasan, S.; Johnson, C. K.; Edwards, C.; Matthews, E. K.; Dolphin, D.; Boyle, R. W. J. Porphyrins Phthalocyanines 2000, 4, 228-232.
44. DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 5983-5993.
45. Coulson, D. R. Inorg. Synth. 1971, 13, 121-124.
46. Buchler, J. W. In The Porphyrins; Dolphin, D., Ed.; Academic Press: Vancouver, 1978; Vol. 1, pp 389-483.
47. SAINT and XPREP; Bruker Nonius Analytical X-ray Instruments, Inc.: Madison, WI, 2003.
48. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
49. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119.
50. Sheldrick, G. M. SHELXL-97; University of Göttingen: Göttingen, Germany, 1998.
51. Engel, R. Handbook of organophosphorus chemistry; M. Dekker: New York, 1992.
52. Therien, M. J. International Patent, WO 02/104072, 2002.
53. Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 3595-3598.
54. For recent reviews see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley and Sons: 2002; Vol. 1, pp 1051-1096.
55. (b) Schwan, A. L. Chem. Soc. Rev. 2004, 33, 218-224.
56. See for example: (a) Sharman, W. M.; Van Lier, J. E. J. Porphyrins Phthalocyanines 2000, 4, 441-453.
57. (b) Setsune, J.-i. J. Porphyrins Phthalocyanines 2004, 8, 93-102.
58. (a) Gao, G. Y.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 6215-6221.
59. (b) Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353-7357.
60. (c) Chen, Y.; Zhang, X. P. J. Org. Chem. 2003, 68, 4432-4438.
61. (d) Gao, G.-Y.; Chen, Y.; Zhang, X. P. Org. Lett. 2004, 6, 1837-1840.
62. (e) Esdaile, L. J.; McMurtrie, J. C.; Turner, P.; Arnold, D. P. Tetrahedron Lett. 2005, 46, 6931-6935.
63. Gao, G.-Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. Org. Lett. 2003, 5, 3261-3264.
64. Gao, G.-Y.; Colvin, A. J.; Chen, Y.; Zhang, X. P. J. Org. Chem. 2004, 69, 8886-8892.
65. Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748-753.
66. Atefi, F.; Locos, O. B.; Senge, M. O.; Arnold, D. P. J. Porphyrins Phthalocyanines 2006, 10, 176-185.
67. Tsuji, J. Palladium reagents and catalysts: innovations in organic synthesis; Wiley and Sons: Chichester; New York, 1996.
68. Imamoto, T.; Takeyama, T.; Kusumoto, T. Chem. Lett. 1985, 1491-1492.
69. Kato, A.; Hartnell, R. D.; Yamashita, M.; Miyasaka, H.; Sugiura, K.-i.; Arnold, D. P. J. Porphyrins Phthalocyanines 2005, 8, 1222-1227.
70. Williams, D. H.; Ward, R. S.; Cooks, R. G. J. Am. Chem. Soc. 1968, 90,; 966-972.
71. Cotton, F. A.; Barnes, R. D.; Bannister, E. J. Chem. Soc. 1960, 2199-2203.
72. Ryppa, C.; Senge, M. O.; Hatscher, S. S.; Kleinpeter, E.; Wacker, P.; Schilde, U.; Wiehe, A. Chem. - Eur. J. 2005, 11, 3427-3442.
73. Brückner, C.; Posakony, J. J.; Johnson, C. K.; Boyle, R. W.; James, B. R.; Dolphin, D. J. Porphyrins Phthalocyanines 1998, 2, 455-465.
74. Ogunsipe, A.; Nyokong, T. J. Porphyrins Phthalocyanines 2005, 9, 121-129.
75. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1-13.
76. Senge, M. O. Chem. Commun. 2006, 243-256.
77. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
78. Inamo, M.; Matsubara, N.; Nakajima, K.; Iwayama, T. S.; Okimi, H.; Hoshino, M. Inorg. Chem. 2005, 44, 6445-6455.
79. Deiters, E.; Bulach, V.; Kyritsakas, N.; Hosseini, M. W. New J. Chem. 2005, 29, 1508-1513.