Syntheses, structures, and electronic and photophysical properties of unsymmetrically substituted butadiynediyl and hexatriynediyl complexes derived from (C6F5)(R3P)2Pt, (p-tol)(R 3P)2Pt, and (Ph3P)Au end-groups

Organometallics

Volumn 27, Issue 19, 2008, Pages 4979-4991

  De Quadras, Laura ^a   Shelton, Abigail H ^b   Kuhn, Helene ^a   Hampel, Frank ^a   Schanze, Kirk S ^b   Gladysz, John A ^a,c  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b University of Florida ^*  (United States)

^c TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYZED REACTIONS; MODIFIED CONDITIONS; PHOTOPHYSICAL PROPERTIES; TRIPLET STATES;

CESIUM; COPPER COMPOUNDS;

PLATINUM;

EID: 54249126855     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800493x     Document Type: Article

References (85)

1. (a) Brady, M.; Weng, W.; Zhou, Y.; Seyler, J. W.; Amoroso, A. J.; Arif, A. M.; Böhme, M.; Frenking, G.; Gladysz, J. A. J. Am. Chem. Soc. 1997, 119, 775.
2. (b) Dembinski, R.; Bartik, T.; Bartik, B.; Jaeger, M.; Gladysz, J. A. J. Am. Chem. Soc. 2000, 122, 810.
3. (c) Meyer, W. E.; Amoroso, A. J.; Horn, C. R.; Jaeger, M.; Gladysz, J. A. Organometallics 2001, 20, 1115.
4. (d) Horn, C. R.; Gladysz, J. A. Eur. J. Inorg. Chem. 2003, 9, 2211.
5. Mohr, W.; Stahl, J.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2003, 9, 3324.
6. Zheng, Q.; Bohling, J. C.; Peters, T. B.; Frisch, A. C.; Hampel, F.; Gladysz, J. A. Chem.-Eur. J. 2006, 12, 6486.
7. Owen, G. R.; Hampel, F.; Gladysz, J. A. Organometallics 2004, 23, 5893.
8. Zheng, Q.; Hampel, F.; Gladysz, J. A. Organometallics 2004, 23, 5896.
9. (a) Stahl, J.; Mohr, W.; de Quadras, L.; Peters, T. B.; Bohling, J. C.; Martin-Alvarez, J. M.; Owen, G. R.; Hampel, F.; Gladysz, J. A. J. Am. Chem. Soc. 2007, 129, 8282.
10. (b) de Quadras, L.; Bauer, E. B.; Mohr, W.; Bohling, J. C.; Peters, T. B.; Martín-Alvarez, J. M.; Hampel, F.; Gladysz, J. A. J. Am. Chem. Soc. 2007, 129, 8296.
11. (c) de Quadras, L.; Bauer, E. B.; Stahl, J.; Zhuravlev, F.; Hampel, F.; Gladysz, J. A. New J. Chem. 2007, 31, 1594.
12. (d) Owen, G. R.; Stahl, J.; Hampel, F.; Gladysz, J. A. Chem.- Eur. J. 2008, 14, 73.
13. Stahl, J.; Bohling, J. C.; Peters, T. B.; de Quadras, L.; Gladysz, J. A. Pure Appl. Chem. 2008, 80, 459.
14. Silverman, E. E.; Cardolaccia, T.; Zhao, X.; Kim, K.-Y.; Haskins-Glusac, K.; Schanze, K. S. Coord. Chem. Rev. 2005, 249, 1491.
15. Farley, R. T.; Zheng, Q.; Gladysz, J. A.; Schanze, K. S. Inorg. Chem. 2008, 47, 2955.
16. (a) Weng, W.; Bartik, T.; Brady, M.; Bartik, B.; Ramsden, J. A.; Arif, A. M.; Gladysz, J. A. J. Am. Chem. Soc. 1995, 117, 11922.
17. (b) Falloon, S. B.; Szafert, S.; Arif, A. M.; Gladysz, J. A. Chem.-Eur. J. 1998, 4, 1033.
18. (a) Paul, F.; Meyer, W. E.; Toupet, L.; Jiao, H.; Gladysz, J. A.; Lapinte, C. J. Am. Chem. Soc. 2000, 122, 9405.
19. (b) Jiao, H.; Costuas, K.; Gladysz, J. A.; Halet, J.-F.; Guillemot, M.; Toupet, L.; Paul, F.; Lapinte, C. J. Am. Chem. Soc. 2003, 125, 9511.
20. (c) Szafert, S.; Paul, F.; Meyer, W. E.; Gladysz, J. A.; Lapinte, C. C. R. Chem. 2008, 11, 693.
21. Review literature:(a) Brace, M. I.; Low, P. J. Adv. Organomet. Chem. 2004, 50, 179.
22. (b) Szafert, S.; Gladysz, J. A. Chem. Rev 2003, 103, 4175;
23. 2006, 106, PR1-PR33.
24. Selected lead papers to a now-immense literature: (a) Lapinte, C. J. Organomet. Chem. 2008, 693, 793.
25. (b) Brace, M. I.; Low, P. J.; Costuas, K.; Halet, J.-F.; Best, S. P.; Heath, G. A. J. Am. Chem. Soc. 2000, 122, 1949.
26. (c) Xu, G.-L.; Zou, G.; Ni, Y.-H.; DeRosa, M. C.; Cratchley, R. J.; Ren, T. J. Am. Chem. Soc. 2003, 125, 10057.
27. (d) Akita, M.; Sakurai, A.; Chung, M.-C.; Moro-oka, Y. J. Organomet. Chem. 2003, 670, 2.
28. (e) Venkatesan, K.; Fox, T.; Schmalle, H. W.; Berke, H. Organometallics 2005, 24, 2834.
29. (f) Qi, H.; Gupta, A.; Noll, B. C.; Snider, G. L.; Lu, Y.; Lent, C.; Fehlner, T. P. J. Am. Chem. Soc. 2005, 127, 15218.
30. Heterobimetallic polyynediyl complexes especially relevant to this study: (a) Antonova, A. B.; Bruce, M. I.; Ellis, B. G.; Gaudio, M.; Humphrey, P. A.; Jevric, M.; Melino, G.; Nicholson, B. K.; Perkins, G. J.; Skelton, B. W.; Stapleton, B.; White, A. H.; Zaitseva, N. N. Chem. Commun. 2004, 960.
31. (b) Bruce, M. I.; Hall, B. C.; Low, P. J.; Smith, M. E.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2000, 300-302, 633.
32. (c) Bruce, M. I.; Costuas, K.; Davin, T.; Ellis, B. G.; Halet, J.-F.; Lapinte, C.; Low, P. J.; Smith, M. E.; Skelton, B. W.; Toupet, L.; White, A. H. Organometallics 2005, 24, 3864.
33. (d) Bruce, M. I.; Jevric, M.; Skelton, B. W.; Smith, M. E.; White, A. H.; Zaitseva, N. N. J. Organomet. Chem. 2006, 691, 361.
34. Other literature especially relevant to this study: (a) Coat, F.; Guillevic, M.-A.; Toupet, L.; Paul, F.; Lapinte, C. Organometallics 1997, 16, 5988.
35. (b) Coat, F.; Guillemot, M.; Paul, F.; Lapinte, C. J. Organomet. Chem. 1999, 578, 76.
36. de Quadras, L. Doctoral Dissertation, Universität Erlangen-Nürnberg, 2006.
37. Stahl, J. Doctoral Dissertation, Universität Erlangen-Nürnberg, 2003.
38. (a) Sonogashira, K.; Fujikura, Y.; Yatake, T.; Toyoshima, N.; Takahashi, S.; Hagihara, N. J. Organomet. Chem. 1978, 145, 101.
39. (b) Ogawa, H.; Onitsuka, K.; Joh, T.; Takahashi, S.; Yamamoto, Y.; Yamakazi, H. Organometallics 1988, 7, 2257, and earlier papers cited therein.
40. 2Pt end-groups (cat. CuI or CuCl at RT to 40 °C): Zheng, Q. Unpublished data including final research report, Universität Erlangen-Nürnberg, 2006.
41. Grim, S. O.; Keiter, R. L.; McFarlane, W. Inorg. Chem. 1967, 6, 1133.
42. Antonova, A. B.; Bruce, M. I.; Humphrey, P. A.; Gaudio, M.; Nicholson, B. K.; Scoleri, N.; Skelton, B. W.; White, A. H.; Zaitseva, N. N. J. Organomet. Chem. 2006, 691, 4694.
43. (a) Bruce, M. I.; Costuas, K.; Halet, J.-F.; Hall, B. C.; Low, P. J.; Nicholson, B. K.; Skeleton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 2002, 383.
44. (b) Bruce, M. I.; Hall, B. C.; Skeleton, B. W.; Smith, M. E.; White, A. H. J. Chem. Soc., Dalton Trans. 2002, 995.
45. (c) See also: Vicente, J.; Chicote, M.-T.; Alvarez-Falcón, M. M. Organometallics 2005, 24, 2764.
46. Bruce, M. I.; Nicholson, B. K.; Bin Shawkataly, O. Inorg. Synth. 1989, 26, 324.
47. Hoffman, N. W. Inorg. Chim. Acta 1984, 88, 59.
48. Bruce, M. I.; Ke, M.; Low, P. J.; Skelton, B. W.; White, A. H. Organometallics 1998, 17, 3539.
49. (a) Bohling, J. C.; Peters, T. B.; Arif, A. M.; Hampel, F.; Gladysz, J. A. In Coordination Chemistry at the Turn of the Century, Ondrejoviç, G., Sirota, A. Eds.; Slovak Technical University Press: Bratislava, Slovakia, 1999; pp 47-52.
50. (b) Peters, T. B.; Zheng, Q.; Stahl, J.; Bohling, J. C.; Arif, A. M.; Hampel, F.; Gladysz, J. A. J. Organomet. Chem. 2002, 641, 53.
51. (c) Mohr, W.; Peters, T. B.; Bohling, J. C.; Hampel, F.; Arif, A. M.; Gladysz, J. A. C. R. Chem. 2002, 5, 111.
52. Zhuravlev, F.; Gladysz, J. A. Chem.-Eur. J. 2004, 10, 6510.
53. Whittle, C. E.; Weinstein, J. A.; George, M. W.; Schanze, K. S. Inorg. Chem. 2001, 40, 4053.
54. Eastmond, R.; Johnson, T. R.; Walton, D. R. M. J. Organomet. Chem. 1973, 50, 87.
55. nPt complexes (n = 1-3), see ref 18b and (a) Sünkel, K.; Birk, U.; Robl, C. Organometallics 1994, 13, 1879.
56. (b) Klein, A.; Klinkhammer, K.-W.; Scheiring, T. J. Organomet. Chem. 1999, 592, 128.
57. (c) Müller, C.; Lachicotte, R. J.; Jones, W. D. Organometallics 2002, 21, 1190.
58. (d) Wong, W.-Y.; Wong, C.-K.; Lu, G.-L.; Cheah, K.-W.; Shi, J.-X.; Lin, Z. J. Chem. Soc., Dalton Trans. 2002, 4587.
59. (e) Yam, V. W.- W.; Wong, K. M.-C.; Zhu, N. Angew. Chem., Int. Ed 2003, 42, 1400;
60. Angew. Chem. 2003, 115, 1438.
61. (a) Brizius, G.; Billingsley, K.; Smith, M. D.; Bunz, U. H. F. Org. Lett. 2003, 5, 3951.
62. (b) Toyota, S.; Iida, T.; Kunizane, C.; Tanifuji, N.; Yoshida, Y. Org. Biomol. Chem. 2003, 1, 2298.
63. (c) Makino, T.; Toyota, S. Bull. Chem. Soc. Jpn. 2005, 78, 917.
64. (d) Toyota, S.; Yanagihara, T.; Yoshida, Y.; Goichi, M. Bull. Chem. Soc. Jpn. 2005, 78, 1351.
65. (e) Miljaniæ, O. S.; Han, S.; Holmes, D.; Schaller, G. R.; Vollhardt, K. P. C. Chem. Commun. 2005, 2606.
66. (f) Nandy, R.; Subramoni, M.; Varghese, B.; Sankararaman, S. J. Org. Chem. 2007, 72, 938.
67. Liau, R.-Y.; Schier, A.; Schmidbaur, H. Organometallics 2003, 22, 3199.
68. (a) Scudder, M.; Dance, I. Chem.-Eur. J. 2002, 8, 5456.
69. (b) Dance, I.; Scudder, M. New J. Chem. 1998, 481.
70. For other mixed valence diplatinum radical cations, see: Klein, A.; Kaim, W. Organometallics 1995, 14, 1176.
71. Che, C.-M.; Chao, H.-Y.; Miskowski, V. M.; Li, Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 4985.
72. (a) Glusac, K.; Kose, M. E.; Jiang, H.; Schanze, K. S. J. Phys. Chem. B 2007, 111, 929.
73. (b) Cooper, T. M.; Blaudeau, J.-P.; Hall, B. C.; Rogers, J. E.; McLean, D. G.; Liu, Y.; Toscano, J. P. Chem. Phys. Lett. 2004, 400, 239.
74. Dey, S. Work in progress, Texas A&M University.
75. DSC and TGA data were treated as recommended by: Cammenga, H. K.; Epple, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1171;
76. e values best represent the temperature of the phase transition or exotherm.
77. 195Pt = 33.8%) and is not reflected in the peak multiplicity given.
78. 2,3,6d,7
79. CP values represent the apparent couplings between adjacent peaks of the triplet.
80. -1 cm-1).
81. FAB, 3-NBA: m/z for the most intense peak of the isotope envelope; relative intensities (%) are for the specified mass range.
82. (a) Collect data collection software; Nonius B.V., 1998.
83. (b) Scalepack data processing software: Otwinowski, Z.; Minor, W. in Methods Enzymol. 1997, 276, 307.
84. Sheldrick, G. M. SHELX-97, Program for refinement of crystal structures; University of Göttingen, 1997.
85. Cromer, D. T.; Waber, J. T. In International Tables for X-ray Crystallography; Ibers, J. A., Hamilton, W. C., Eds.; Kynoch: Birmingham, England, 1974.