Organic triplet emissions of arylacetylide moieties harnessed through coordination to [Au(PCy3)]+. Effect of molecular structure upon photoluminescent properties

Journal of the American Chemical Society

Volumn 124, Issue 49, 2002, Pages 14696-14706

  Chao, Hsiu Yi ^a   Lu, Wei ^a   Li, Yanqin ^a   Chan, Michael C W ^a   Che, Chi Ming ^a   Cheung, Kung Kai ^a   Zhu, Nianyong ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL LATTICES; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS; PHOSPHORESCENCE; PHOTOLUMINESCENCE; REDUCTION; X RAY CRYSTALLOGRAPHY;

LOWEST-ENERGY SINGLET TRANSITIONS;

GOLD COMPOUNDS;

ACETIC ACID DERIVATIVE; ACETYLENE DERIVATIVE; GOLD COMPLEX; LIGAND; PHENYL GROUP;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CRYSTAL STRUCTURE; DESTRUCTION; ENERGY; FLAME PHOTOMETRY; FLUORESCENCE; MOLECULAR INTERACTION; PHOTOLUMINESCENCE; VIBRATION; X RAY CRYSTALLOGRAPHY;

EID: 0037065288     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0209417     Document Type: Article

References (86)

1. (a) Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350-1377.
2. (b) Stang, P. J.; Diederich, F. Modern Acetylene Chemistry; VCH: Weinheim, Germany, 1995.
3. (c) Carter, G. M.; Chen, Y. J.; Rubner, M. F.; Sandman, D. J.; Thakur, M. K.; Tripathy, S. K. In Non-Linear Optical Properties of Organic Molecules and Crystals: Chemla, D. S., Zyss, J., Eds.; Academic: Orlando, FL. 1987; Vol. 2, Chapter III-3, p 85.
4. (a) Beeby, A.; Findlay, K.; Low, P. J.; Marder, T. B. J. Am. Chem. Soc. 2002, 124, 8280-8284.
5. (b) Kim, J.; Levitsky, I. A.; McQuade, D. T.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 7710-7718.
6. (c) Cornil, J.; Karzazi, Y.; Brédas, J. L. J. Am. Chem. Soc. 2002, 124, 3516-3517.
7. (d) Sluch, M. I.; Godt, A.; Bunz, U. H. F.; Berg, M. A. J. Am. Chem. Soc. 2001, 123, 6447-6448.
8. (e) Levitus, M.; Schmieder, K.; Ricks, H.; Shimizu, K. D.; Bunz, U. H. F.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2001, 123, 4259-4265.
9. (f) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-804.
10. (g) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644.
11. (h) McQuade, D. T.; Kim, J.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 5885-5886.
12. (i) Deans, R.; Kim, J.; Machacek, M. R.; Swager, T. M. J. Am. Chem. Soc. 2000, 122, 8565-8566.
13. (j) Sato, T.; Jiang, D. L.; Aida, T. J. Am. Chem. Soc. 1999, 121, 10658-10659.
14. (k) Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873.
15. (l) Montali, A.; Bastiaansen, C.; Smith, P.; Weder, C. Nature 1998, 392, 261-264.
16. (m) Pang, Y.; Li, J.; Hu, B.; Karasz, F. E. Macromolecules, 1998, 31, 6730-6732.
17. (n) Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413.
18. (a) Manna, J.; John, K. D.; Hopkins, M. D. Adv. Organomet. Chem. 1995, 38, 79-154.
19. (b) Fujikura, Y.; Sonogashira, K.; Hagihara, N. Chem. Lett. 1975, 1067-1070.
20. (c) Ma, Y. G.; Chan, W. H.; Zhou, X. M.; Che, C. M. New J. Chem. 1999, 23, 263-265.
21. (d) Chan, S. C.; Chan, M. C. W.; Wang, Y.; Che, C. M.; Cheung, K. K.; Zhu, N. Chem.-Eur. J. 2001, 7, 4180-4190.
22. (e) Lu, W.; Mi, B. X.; Chan, M. C. W.; Hui, Z.; Zhu, N.; Lee, S. T.; Che, C. M. Chem. Commun. 2002, 206-207.
23. (f) Long, N. J. In Optoelectronic Properties of Inorganic Compounds; Roundhill, D. M., Fackler, J. P., Jr., Eds.; Plenum Press: New York. 1999; Chapter 4.
24. (g) Mingos, D. M. P.; Yau, J.; Menzer, S.; Williams., D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1894-1895.
25. (h) Lavastre, O.; Plass, J.; Bachmann, P.; Guesmi, S.; Moinet, C.; Dixneuf, P. H. Organometallics 1997, 16, 184-189.
26. (i) McDonagh, A. M.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B.; Houbrechts, S.; Wada, T.; Sasabe, H.; Persoons, A. J. Am. Chem. Soc. 1999, 121, 1405-1406.
27. (j) John, K. D.; Hopkins, M. D. Chem. Commun. 1999, 589-590.
28. (k) Walters, K. A.; Dattelbaum, D. M.; Ley, K. D.; Schoonover, J. R.; Meyer, T. J.; Schanze, K. S. Chem. Commun. 2001, 1834-1835.
29. (a) Wittmann, H. F.; Friend, R. H.; Khan, M. S.; Lewis, J. J. Chem. Phys. 1994, 101, 2693-2698.
30. (b) Younus, M.; Köhler, A.; Cron, S.; Chawdhury, N.; Al-Mandhary, M. R. A.; Khan, M. S.; Lewis, J.; Long, N. J.; Friend, R. H.; Raithby, P. R. Angew. Chem., Int. Ed. 1998, 37, 3036-3039.
31. (c) Chawdhury, N.; Köhler, A.; Friend, R. H.; Wong, W. Y.; Lewis, J.; Younus, M.; Raithby, P. R.; Corcoran, T. C.; Al-Mandhary, M. R. A.; Khan, M. S. J. Chem. Phys. 1999, 110, 4963-4970.
32. (d) Wilson, J. S.; Köhler, A.; Friend, R. H.; Al-Suti, M. K.; Al-Mandhary, M. R. A.; Khan, M. S.; Raithby, P. R. J. Chem. Phys. 2000, 113, 7627-7634.
33. (e) Wilson, J. S.; Chawdhury, N.; Al-Mandhary, M. R. A.; Younus, M.; Khan, M. S.; Raithby, P. R.; Köhler, A.; Friend, R. H. J. Am. Chem. Soc. 2001, 123, 9412-9417.
34. (f) Köhler, A.; Wilson, J. S.; Friend, R. H.; Al-Suti, M. K.; Khan, M. S.; Gerhard, A.; Bässler, H. J. Chem. Phys. 2002, 116, 9457-9463.
35. (g) Wilson, J. S.;: Dhoot, A. S.; Seeley, A. J. A. B.; Khan, M. S.; Köhler, A.; Friend, R. H. Nature 2001, 413, 828-831.
36. (h) Nguyen, P.; Gómez-Elipe, P.; Manners, I. Chem. Rev. 1999, 99, 1515-1548.
37. For selected examples, see: (a) Li, D.; Hong, X.; Che, C. M.; Lo, W. C.; Peng, S. M. J. Chem. Soc., Dalton Trans. 1993, 2929-2932.
38. (b) Shieh, S. J.; Hong, X.; Peng, S. M.; Che, C. M. J. Chem. Soc., Dalton Trans. 1994, 3067-3068.
39. (c) Xiao, H.; Cheung, K. K.; Che, C. M. J. Chem. Soc., Dalton Trans. 1996, 3699-3703.
40. (d) Yam, V. W. W.; Choi, S. W. K. J. Chem. Soc., Dalton Trans. 1996, 4227-4232.
41. (e) Yam, V. W. W.; Choi, S. W. K.; Cheung, K. K. Organometallics 1996, 15, 1734-1739.
42. (f) Tzeng, B. C.; Lo, W. C.; Che, C. M.; Peng, S. M. Chem. Commun. 1996, 181-182.
43. (g) Irwin, M. J.; Vittal, J. J.; Puddephatt, R. J. Organometallics 1997, 16, 3541-3547.
44. (h) Hunks, W. J.; MacDonald, M. A.; Jennings, M. C.; Puddephatt, R. J. Organometallics 2000, 19, 5063-5070.
45. (i) Lin, Y. Y.; Lai, S. W.; Che, C. M.; Cheung, K. K.; Zhou, Z. Y. Organometallics 2002, 21, 2275-2282.
46. (a) Che, C. M.; Chao, H. Y.; Miskowski, V. M.; Li, Y.; Cheung, K. K. J. Am. Chem. Soc. 2001, 123, 4985-4991.
47. (b) Lu, W.; Xiang, H. F.; Zhu, N.; Che, C. M. Organometallics 2002, 21, 2343-2346.
48. Lai, S. W.; Chan, M. C. W.; Cheung, T. C.; Peng, S. M.; Che, C. M. Inorg. Chem. 1999, 38, 4046-4055.
49. Kende, A. S.; Smith, C. A. J. Org. Chem. 1988, 53, 2655-2657.
50. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
51. Ciana, L. D.; Haim, A. J. Heterocycl. Chem. 1984, 21, 607-608.
52. Khan, M. S.; Kakkar, A. K.; Long, N. J.; Lewis, J.; Raithby, P.; Nguyen, P.; Marder, T. B.; Wittmanm, F.; Friend, R. H. J. Mater. Chem. 1994, 4, 1227-1232.
53. Lavastre, O.; Ollivier, L.; Dixneuf, P. H.; Sibandhit, S. Tetrahedron 1996, 52, 5495-5504.
54. Al-sa'ady, A. K.; McAuliffe, C. A.; Parish, R. V.; Sandbank, J. A. Inorg. Synth. 1985, 23, 191-194.
55. Wu, I. Y.; Lin, J. T.; Luo, J.; Sun, S. S.; Li, C. S.; Lin, K. J.; Tsai, C.; Hsu, C. C.; Lin, J. L. Organometallics 1997, 16, 2038-2048.
56. (a) Bruce, M. I.; Horn, E.; Marisons, J. G.; Snow, M. R. Aust. J. Chem. 1984, 37, 1163-1170.
57. (b) Cross, R. J.; Davidson, M. F. J. Chem. Soc., Dalton Trans. 1986, 411-414.
58. (c) Irwin, M. J.; Rendina, L. M.; Vittal, J. J.; Puddephatt, R. J. Chem. Commun. 1996, 1281-1282.
59. Vicente, J.; Chicote, M. T.; Abrisqueta, M. D.; Jones, P. G. Organometaltics 1997, 16, 5628-5636.
60. (a) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738-5745.
61. (b) Naulty, R. H.; Cifuentes, M. P.; Humphrey, M. G.; Houbrechts, S.; Boutton, C.; Persoons, A.; Heath, G. A.; Hockless, D. C. R.; Luther-Davies, B.; Samoc, M. J. Chem. Soc., Dalton Trans. 1997, 4167-4174.
62. Muir, J. A.; Muir, M. M.; Pulgar, L. B.; Jones, P. G.; Sheldrick, G. M. Acta Crystrallogr. 1985, C41, 1174-1176.
63. (a) Jia, G.; Puddephatt, R. J.; Scott, J. D.; Vittal, J. J. Organometallics 1993, 12, 3565-3574.
64. (b) Irwin, M. J.; Jia, G.; Payne, N. C.; Puddephatt, R. J. Organometallics 1996, 15, 51-57.
65. (c) MacDonald, M. A.; Puddephatt, R. J.; Yap, G. P. A. Organometallics 2000, 19, 2194-2199.
66. (a) Bruce, M. I.; Hall, B. C.; Kelly, B. D.; Low, P. J.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1999, 3719-3728.
67. (b) Low, P. J.; Bruce, M. I. Adv. Organomet. Chem. 2001, 48, 71-288.
68. (a) Bruce, M. I.; Hall, B. C.; Skelton, B. W.; Smith, M. E.; White, A. H. J. Chem. Soc., Dalton Trans. 2002, 995-1001.
69. (b) Akita, M.; Chung, M. C.; Sakurai, A.; Sugimoto, S.; Terada, M.; Tanaka, M.; Moro-oka, Y. Organometallics 1997, 16, 4882-4888.
70. (c) Sun, Y.; Taylor, N. J.; Carty, A. J. Organometallics 1992, 11, 4293-4300.
71. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
72. Suppan, P. Chemistry and Light; Royal Society of Chemistry: Cambridge, U.K., 1994: p 76.
73. Sacksteder, L.; Baralt, E.; DeGraff, B. A.; Lukehart, C. M.; Demas, J. N. Inorg. Chem. 1991, 30, 2468-2476.
74. 2), and glassy states are very similar. It is, therefore, highly unlikely that the dual emission originates from aggregate species or a small amount of unmetalated impurity within an aggregate.
75. Turro, N. J. Modern Molecular Photochemistry; The Benjamin/Cummings Publishing Company: Menlo Park, California, 1978; pp 146-148 and 343-344.
76. -3 joule/pulse, the ratio of fluorescence to phosphorescence signal was observed to increase from 1.5 to 2.8. This is consistent with a triplet-triplet annihilation mechanism for the delayed fluorescence. We are grateful to the reviewers for suggesting this experiment.
77. Marshall, J. L.; Stobart, S. R.; Gray, H. B. J. Am. Chem. Soc. 1984, 106, 3027-3029.
78. pa of the oxidation wave is determined.
79. 2-4] species in: Hurst, S. K.; Cifuentes, M. P.; Morrall, J. P. L.; Lucas, N. T.; Whittall, I. R.; Humphrey, M. G.; Asselberghs, I.; Persoons, A.; Samoc, M.; Luther-Davies, B.; Willis, A. C. Organometallics 2001, 20, 4664-4675.
80. Mangel, T.; Eberhardt, A.; Scherf, U.; Bunz, U. H. F.; Müllen, K. Macromol. Rapid Commun. 1995, 16, 571-580.
81. Because complexes 6 and 12 do not display phosphorescence in dichloromethane at 298 K, their phosphorescent emission energies are taken from 77 K alcoholic glasses.
82. Hertel, D.; Setayesh, S.; Nothofer, H. G.; Scherf, U.; Müllen, K.; Bässler, H. Adv. Mater. 2001, 13, 65-70.
83. Monkman, A. P.; Burrows, H. D.; Hartwell, L. J.; Horsburgh, L. E.; Hamblett, I.; Navaratnam, S. Phys. Rev. Lett. 2001, 86, 1358-1361.
84. This estimate may be regarded as the approximate "intrinsic" value for the polymer, since macromolecular effects such as interchain interactions have not been considered; the estimated value may, therefore, be more appropriate for an isolated polymer chain in dilute solutions or inert matrixes. See: Comil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brédas, J. L. J. Am. Chem. Soc. 1998, 120, 1289-1299.
85. (a) Siebrand, W. J. Chem. Phys. 1967, 47, 2411-2422.
86. (b) Englman, R.; Jortner, J. Mol. Phys. 1970, 18, 145-164.