Pyridyl gold(I) alkynyls: A synthetic, structural, spectroscopic, and computational study

Organometallics

Volumn 29, Issue 23, 2010, Pages 6186-6195

  Kilpin, Kelly J ^a   Horvath, Raphael ^a   Jameson, Geoffrey B ^b   Telfer, Shane G ^b,c   Gordon, Keith C ^a,c   Crowley, James D ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b MASSEY UNIVERSITY   (New Zealand)

^c MACDIARMID INSTITUTE FOR ADVANCED MATERIALS AND NANOTECHNOLOGY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

4-AMINOPYRIDINE; ALKYNYL COMPLEXES; ALKYNYLS; AUROPHILIC INTERACTION; BUILDING BLOCKES; COMPUTATIONAL STUDIES; COORDINATE COMPLEXES; DENSITY FUNCTIONAL THEORY CALCULATIONS; ELECTRON-RICH; NANO-SCALE MATERIALS; ORGANOMETALLIC COMPLEX; PYRIDINE LIGANDS; PYRIDYL; SELF-ASSEMBLED; SOLID-STATE STRUCTURES; STRUCTURAL CHARACTERIZATION;

COMPLEXATION; DENSITY FUNCTIONAL THEORY; DIMERS; ELECTRONIC STRUCTURE; GOLD; ORGANOMETALLICS; PYRIDINE; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

GOLD COMPOUNDS;

EID: 78649836826     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1003978     Document Type: Article

References (126)

1. Elemans, J. A. A. W.; van Hameren, R.; Nolte, R. J. M.; Rowan, A. E. Adv. Mater. 2006, 18 (10) 1251-1266
2. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105 (4) 1491-1546
3. Schenning, A. P. H. J.; Meijer, E. W. Chem. Commun. 2005, 26) 3245-3258
4. Shimizu, T.; Masuda, M.; Minamikawa, H. Chem. Rev. 2005, 105 (4) 1401-1443
5. Simpson, C. D.; Wu, J.; Watson, M. D.; Muellen, K. J. Mater. Chem. 2004, 14 (4) 494-504
6. Yamamoto, T.; Fukushima, T.; Aida, T. Adv. Polym. Sci. 2008, 220 (Self-Assembled Nanomaterials II) 1-27
7. Bremi, J.; Caseri, W.; Smith, P. J. Mater. Chem. 2001, 11 (10) 2593-2596
8. Caseri, W. R.; Chanzy, H. D.; Feldman, K.; Fontana, M.; Smith, P.; Tervoort, T. A.; Goossens, J. G. P.; Meijer, E. W.; Schenning, A. P. H. J.; Dolbnya, I. P.; Debije, M. G.; de Haas, M. P.; Warman, J. M.; van de Craats, A. M.; Friend, R. H.; Sirringhaus, H.; Stutzmann, N. Adv. Mater. 2003, 15 (2) 125-129
9. Debije, M. G.; de Haas, M. P.; Savenije, T. J.; Warman, J. M.; Fontana, M.; Stutzmann, N.; Caseri, W. R.; Smith, P. Adv. Mater. 2003, 15 (11) 896-899
10. Debije, M. G.; De Haas, M. P.; Warman, J. M.; Fontana, M.; Stutzmann, N.; Kristiansen, M.; Caseri, W. R.; Smith, P.; Hoffmann, S.; Solling, T. I. Adv. Funct. Mater. 2004, 14 (4) 323-328
11. Fontana, M.; Caseri, W.; Smith, P. Platinum Met. Rev. 2006, 50 (3) 112-117
12. Fontana, M.; Chanzy, H.; Caseri, W. R.; Smith, P.; Schenning, A. P. H. J.; Meijer, E. W.; Groehn, F. Chem. Mater. 2002, 14 (4) 1730-1735
13. Kim, E.-G.; Schmidt, K.; Caseri, W. R.; Kreouzis, T.; Stingelin-Stutzmann, N.; Bredas, J.-L. Adv. Mater. 2006, 18 (15) 2039-2043
14. Anderson, B. M.; Hurst, S. K. Eur. J. Inorg. Chem. 2009, 21) 3041-3054
15. Hori, A.; Shinohe, A.; Yamasaki, M.; Nishibori, E.; Aoyagi, S.; Sakata, M. Angew. Chem., Int. Ed. 2007, 46 (40) 7617-7620
16. Chen, Y.; Li, K.; Lu, W.; Chui, S. S.-Y.; Ma, C.-W.; Che, C.-M. Angew. Chem., Int. Ed. 2009, 48 (52) 9909-9913
17. Kui, S. C. F.; Chui, S. S.-Y.; Che, C.-M.; Zhu, N. J. Am. Chem. Soc. 2006, 128 (25) 8297-8309
18. Lu, W.; Chen, Y.; Roy, V. A. L.; Chui, S. S.-Y.; Che, C.-M. Angew. Chem., Int. Ed. 2009, 48 (41) 7621-7625
19. Lu, W.; Chui, S. S.-Y.; Ng, K.-M.; Che, C.-M. Angew. Chem., Int. Ed. 2008, 47 (24) 4568-4572
20. Lu, W.; Law, Y.-C.; Han, J.; Chui, S. S.-Y.; Ma, D.-L.; Zhu, N.; Che, C.-M. Chem. Asian J. 2008, 3 (1) 59-69
21. Lu, W.; Ng, K.-M.; Che, C.-M. Chem. Asian J. 2009, 4 (6) 830-834
22. Lu, W.; Roy, V. A. L.; Che, C.-M. Chem. Commun. 2006, 38) 3972-3974
23. So, M.-H.; Roy, V. A. L.; Xu, Z.-X.; Chui, S. S.-Y.; Yuen, M.-Y.; Ho, C.-M.; Che, C.-M. Chem. Asian J. 2008, 3 (11) 1968-1978
24. Sun, Y.; Ye, K.; Zhang, H.; Zhang, J.; Zhao, L.; Li, B.; Yang, G.; Yang, B.; Wang, Y.; Lai, S.-W.; Che, C.-M. Angew. Chem., Int. Ed. 2006, 45 (34) 5610-5613
25. Tong, G. S.-M.; Che, C.-M. Chem. Eur. J. 2009, 15 (29) 7225-7237
26. Yuen, M.-Y.; Roy, V. A. L.; Lu, W.; Kui, S. C. F.; Tong, G. S. M.; So, M.-H.; Chui, S. S.-Y.; Muccini, M.; Ning, J. Q.; Xu, S. J.; Che, C.-M. Angew. Chem., Int. Ed. 2008, 47 (51) 9895-9899
27. Zhu, M.-X.; Lu, W.; Zhu, N.; Che, C.-M. Chem. Eur. J. 2008, 14 (31) 9736-9746
28. Shieh, S.-J.; Hong, X.; Peng, S.-M.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1994, 20) 3067-8
29. Frischmann, P. D.; Guieu, S.; Tabeshi, R.; MacLachlan, M. J. J. Am. Chem. Soc. 2010, 132 (22) 7668-7675
30. Camerel, F.; Ziessel, R.; Donnio, B.; Bourgogne, C.; Guillon, D.; Schmutz, M.; Iacovita, C.; Bucher, J.-P. Angew. Chem., Int. Ed. 2007, 46 (15) 2659-2662
31. Clark, M. L.; Diring, S.; Retailleau, P.; McMillin, D. R.; Ziessel, R. Chem. Eur. J. 2008, 14 (24) 7168-7179
32. Tam, A. Y.-Y.; Wong, K. M.-C.; Wang, G.; Yam, V. W.-W. Chem. Commun. 2007, 20, 2028-2030
33. Tam, A. Y.-Y.; Wong, K. M.-C.; Yam, V. W.-W. Chem.-Eur. J. 2009, 15 (19) 4775-4778
34. Tam, A. Y.-Y.; Wong, K. M.-C.; Yam, V. W.-W. J. Am. Chem. Soc. 2009, 131 (17) 6253-6260
35. Kozhevnikov, V. N.; Donnio, B.; Bruce, D. W. Angew. Chem., Int. Ed. 2008, 47 (33) 6286-6289
36. Santoro, A.; Whitwood, A. C.; Williams, J. A. G.; Kozhevnikov, V. N.; Bruce, D. W. Chem. Mater. 2009, 21 (16) 3871-3882
37. Cardolaccia, T.; Li, Y.; Schanze, K. S. J. Am. Chem. Soc. 2008, 130 (8) 2535-2545
38. Damm, C.; Israel, G.; Hegmann, T.; Tschierske, C. J. Mater. Chem. 2006, 16 (19) 1808-1816
39. Hutchings, G. J.; Brust, M.; Schmidbaur, H. Chem. Soc. Rev. 2008, 37 (9) 1759-1765
40. Laguna, A., Ed. Modern Supramolecular Gold Chemistry: Gold-Metal Interactions And Applications; Wiley: New York, 2008; 505 pp.
41. Puddephatt, R. J. Chem. Soc. Rev. 2008, 37 (9) 2012-2027
42. Schmidbaur, H. Gold Bull. 2000, 33 (1) 3-10
43. Schmidbaur, H. Nature 2001, 413 (6851) 31-33
44. Schmidbaur, H.; Schier, A. Chem. Soc. Rev. 2008, 37 (9) 1931-1951
45. Hogarth, G.; Alvarez-Falcon, M. M. Inorg. Chim. Acta 2005, 358 (5) 1386-1392
46. Hunks, W. J.; MacDonald, M.-A.; Jennings, M. C.; Puddephatt, R. J. Organometallics 2000, 19 (24) 5063-5070
47. Partyka, D. V.; Gao, L.; Teets, T. S.; Updegraff, J. B.; Deligonul, N.; Gray, T. G. Organometallics 2009, 28 (21) 6171-6182
48. Partyka, D. V.; Updegraff, J. B., III; Zeller, M.; Hunter, A. D.; Gray, T. G. Organometallics 2007, 26 (1) 183-186
49. Schuster, O.; Liau, R.-Y.; Schier, A.; Schmidbaur, H. Inorg. Chim. Acta 2005, 358 (5) 1429-1441
50. Yip, S.-K.; Lam, W. H.; Zhu, N.; Yam, V. W.-W. Inorg. Chim. Acta 2006, 359 (11) 3639-3648
51. Habermehl, N. C.; Eisler, D. J.; Kirby, C. W.; Yue, N. L. S.; Puddephatt, R. J. Organometallics 2006, 25 (12) 2921-2928
52. Habermehl, N. C.; Jennings, M. C.; McArdle, C. P.; Mohr, F.; Puddephatt, R. J. Organometallics 2005, 24 (21) 5004-5014
53. Hunks, W. J.; Jennings, M. C.; Puddephatt, R. J. Z. Naturforsch., B: Chem. Sci. 2004, 59 (11/12) 1488-1496
54. Hunks, W. J.; Lapierre, J.; Jenkins, H. A.; Puddephatt, R. J. Dalton Trans. 2002, 14) 2885-2889
55. Irwin, M. J.; Vittal, J. J.; Puddephatt, R. J. Organometallics 1997, 16 (15) 3541-3547
56. Jia, G.; Payne, N. C.; Vittal, J. J.; Puddephatt, R. J. Organometallics 1993, 12 (12) 4771-8
57. Jia, G.; Puddephatt, R. J.; Scott, J. D.; Vittal, J. J. Organometallics 1993, 12 (9) 3565-74
58. Jia, G.; Puddephatt, R. J.; Vittal, J. J. J. Organomet. Chem. 1993, 449 (1-2) 211-17
59. Jia, G.; Puddephatt, R. J.; Vittal, J. J.; Payne, N. C. Organometallics 1993, 12 (2) 263-5
60. McArdle, C. P.; Irwin, M. J.; Jennings, M. C.; Puddephatt, R. J. Angew. Chem., Int. Ed. 1999, 38 (22) 3376-3378
61. McArdle, C. P.; Irwin, M. J.; Jennings, M. C.; Vittal, J. J.; Puddephatt, R. J. Chem. Eur. J. 2002, 8 (3) 723-734
62. McArdle, C. P.; Jennings, M. C.; Vittal, J. J.; Puddephatt, R. J. Chem. Eur. J. 2001, 7 (16) 3572-3583
63. McArdle, C. P.; Van, S.; Jennings, M. C.; Puddephatt, R. J. J. Am. Chem. Soc. 2002, 124 (15) 3959-3965
64. McArdle, C. P.; Vittal, J. J.; Puddephatt, R. J. Angew. Chem., Int. Ed. 2000, 39 (21) 3819-3822
65. Mohr, F.; Eisler, D. J.; McArdle, C. P.; Atieh, K.; Jennings, M. C.; Puddephatt, R. J. J. Organomet. Chem. 2003, 670 (1-2) 27-36
66. Mohr, F.; Jennings, M. C.; Puddephatt, R. J. Eur. J. Inorg. Chem. 2003, 2) 217-223
67. Mohr, F.; Jennings, M. C.; Puddephatt, R. J. Angew. Chem., Int. Ed. 2004, 43 (8) 969-971
68. Payne, N. C.; Ramachandran, R.; Puddephatt, R. J. Can. J. Chem. 1995, 73 (1) 6-11
69. Qin, Z.; Jennings, M. C.; Puddephatt, R. J. Chem. Eur. J. 2002, 8 (3) 735-738
70. Bruce, M. I.; Horn, E.; Matisons, J. G.; Snow, M. R. Aust. J. Chem. 1984, 37, 1163-1170
71. Bruce, M. I.; Hall, B. C.; Skelton, B. W.; Smith, M. E.; White, A. H. Dalton Trans. 2002, 6) 995-1001
72. Bruce, M. I.; Jevric, M.; Skelton, B. W.; Smith, M. E.; White, A. H.; Zaitseva, N. N. J. Organomet. Chem. 2006, 691 (3) 361-370
73. Khairul, W. M.; Fox, M. A.; Zaitseva, N. N.; Gaudio, M.; Yufit, D. S.; Skelton, B. W.; White, A. H.; Howard, J. A. K.; Bruce, M. I.; Low, P. J. Dalton Trans. 2009, 4) 610-620
74. Lin, J. C. Y.; Tang, S. S.; Vasam, C. S.; You, W. C.; Ho, T. W.; Huang, C. H.; Sun, B. J.; Huang, C. Y.; Lee, C. S.; Hwang, W. S.; Chang, A. H. H.; Lin, I. J. B. Inorg. Chem. 2008, 47 (7) 2543-2551
75. Chiou, J. Y. Z.; Luo, S. C.; You, W. C.; Bhattacharyya, A.; Vasam, C. S.; Huang, C. H.; Lin, I. J. B. Eur. J. Inorg. Chem. 2009, 13) 1950-1959
76. Fernandez, E. J.; Laguna, A.; Lopez-de-Luzuriaga, J. M.; Monge, M.; Montiel, M.; Olmos, M. E.; Perez, J.; Rodriguez-Castillo, M. Gold Bull. 2007, 40 (3) 172-183
77. Crowley, J. D.; Bosnich, B. Eur. J. Inorg. Chem. 2005, 11) 2015-2025
78. Crowley, J. D.; Goshe, A. J.; Bosnich, B. Chem. Commun. 2003, 3) 392-393
79. Crowley, J. D.; Goshe, A. J.; Steele, I. M.; Bosnich, B. Chem. Eur. J. 2004, 10 (8) 1944-1955
80. Crowley, J. D.; Steele, I. M.; Bosnich, B. Inorg. Chem. 2005, 44 (9) 2989-2991
81. Crowley, J. D.; Steele, I. M.; Bosnich, B. Eur. J. Inorg. Chem. 2005, 19) 3907-3917
82. Noviandri, I.; Brown, K. N.; Fleming, D. S.; Gulyas, P. T.; Lay, P. A.; Masters, A. F.; Phillips, L. J. Phys. Chem. B 1999, 103 (32) 6713-6722
83. Yanai, T.; Tew, D. P.; Handy, N. C. Chem. Phys. Lett. 2004, 393 (1-3) 51-57
84. Howell, S. L.; Gordon, K. C.; McGarvey, J. J. J. Phys. Chem. A 2005, 109 (12) 2948-2956
85. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14 (2) 123-134
86. O'Boyle, N. M.; Tenderholt, A. L.; Langner, K. M. J. Comput. Chem. 2008, 29 (5) 839-845
87. 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 (1) 115-119
88. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64 (1) 112-122
89. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30 (5, Pt. 1) 565
90. Coates, G. E.; Parkin, C. J. Chem. Soc. 1962, 3220-6
91. Vicente, J.; Chicote, M. T.; Alvarez-Falcón, M. M.; Abrisqueta, M.-D.; Hernández, F. J.; Jones, P. G. Inorg. Chim. Acta 2003, 347, 67-74
92. Siemeling, U.; Rother, D.; Bruhn, C. Organometallics 2008, 27 (24) 6419-6426
93. Vicente, J.; Chicote, M.-T.; Alvarez-Falcon, M. M.; Jones, P. G. Organometallics 2005, 24 (24) 5956-5963
94. n, however, shows much better solubility and dissolves readily in solvents such as dichloromethane.
95. Weast, R. C., Ed. CRC Handbook of Chemistry and Physics, 68 th ed.; CRC Press: Boca Raton, FL, 1987; 2464 pp.
96. Pham-Tran, N.-N.; Bouchoux, G.; Delaere, D.; Nguyen, M. T. J. Phys. Chem. A 2005, 109 (12) 2957-2963
97. + fragment ion, are observed.
98. n (1). These results suggest that 1a is formed in solution via ligand exchange and then rapidly decomposes to free pyridine and 1. This is completely consistent with our other data on the stability of 1a. Other workers have previously shown that treatment of DMAP-containing complexes with protonated pyridine leads to protonation of the more basic DMAP ligand and coordination of the Py donor group. See: Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Symes, M. D. Chem. Commun. 2010, 46 (14) 2382-2384
99. Crowley, J. D.; Leigh, D. A.; Lusby, P. J.; McBurney, R. T.; Perret-Aebi, L.-E.; Petzold, C.; Slawin, A. M. Z.; Symes, M. D. J. Am. Chem. Soc. 2007, 129 (48) 15085-15090
100. Nast, R.; Pfab, W. Chem. Ber. 1956, 89, 415-421
101. Blake, D.; Calvin, G.; Coates, G. E. Proc. Chem. Soc. 1959, 396-397
102. In the solid state the complexes darken to a purple color (decompose) over a period of 2-3 months in the absence of light.
103. McAdam, C. J.; Blackie, E. J.; Morgan, J. L.; Mole, S. A.; Robinson, B. H.; Simpson, J. Dalton Trans. 2001, 16) 2362-2369
104. Butler, P.; Gallagher, J. F.; Manning, A. R.; Mueller-Bunz, H.; McAdam, C. J.; Simpson, J.; Robinson, B. H. J. Organomet. Chem. 2005, 690 (21-22) 4545-4556
105. Gao, L.; Partyka, D. V.; Updegraff, J. B., III; Deligonul, N.; Gray, T. G. Eur. J. Inorg. Chem. 2009, 18) 2711-2719
106. Siemeling, U.; Rother, D.; Bruhn, C. Chem. Commun. 2007, 41) 4227-4229
107. Yip, S.-K.; Cheng, E. C.-C.; Yuan, L.-H.; Zhu, N.; Yam, V. W.-W. Angew. Chem., Int. Ed. 2004, 43 (37) 4954-4957
108. We also obtained the crystal structure of 1b (see the Supporting Information). While we were readily able to determine the connectivity of 1b, we have been unable to satisfactorily refine the data, despite collecting multiple data sets from several different crystals of reasonable quality. In all cases twinning was observed, which led to poor-quality diffraction data. As observed with the other structures, 1b is a neutral linear two-coordinate complex that dimerizes in the solid state. In this case the formation of the dimer is stabilized by an Au(I)-Au(I) interaction (Au-Au distance 3.19 Å).
109. Janiak, C. Dalton Trans. 2000, 21) 3885-3896
110. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 5) 651-669
111. Tiekink, E. R. T.; Zukerman-Schpector, J. CrystEngComm 2009, 11 (7) 1176-1186
112. Mooibroek, T. J.; Gamez, P.; Reedijk, J. CrystEngComm 2008, 10 (11) 1501-1515
113. To simplify the calculation, the polymeric gold precursor 1 was approximated by a tetrameric complex where the gold atoms bind end-on to the alkyne group of a neighboring complex to give a square arrangement (see the Supporting Information).
114. Walsh, P. J.; Gordon, K. C.; Lundin, N. J.; Blackman, A. G. J. Phys. Chem. A 2005, 109 (26) 5933-5942
115. Johnson, R. D., III. NIST Computational Chemistry Comparison and Benchmark Database; NIST Standard Reference Database Number 101 Release 15: http://cccbdb.nist.gov/, February 2010.
116. McGoverin, C. M.; Walsh, T. J.; Gordon, K. C.; Kay, A. J.; Woolhouse, A. D. Chem. Phys. Lett. 2007, 443 (4-6) 298-303
117. Horvath, R.; Gordon, K. C. Coord. Chem. Rev. 2010, 254 (21-22) 2505-2518
118. Vlcek, A.; Zalis, S. Coord. Chem. Rev. 2007, 251 (3 + 4) 258-287
119. Li, D.; Hong, X.; Che, C. M.; Lo, W. C.; Peng, S. M. J. Chem. Soc., Dalton Trans. 1993, 19, 2929-32
120. Ferrer, M.; Gutierrez, A.; Rodriguez, L.; Rossell, O.; Lima, J. C.; Font-Bardia, M.; Solans, X. Eur. J. Inorg. Chem. 2008, 18, 2899-2909
121. We thank a reviewer for pointing out this interpretation.
122. Elbjeirami, O.; Yockel, S.; Campana, C. F.; Wilson, A. K.; Omary, M. A. Organometallics 2007, 26 (10) 2550-2560
123. Boulet, P.; Chermette, H.; Daul, C.; Gilardoni, F.; Rogemond, F.; Weber, J.; Zuber, G. J. Phys. Chem. A 2001, 105 (5) 885-894
124. This quantity was obtained by comparison of TD-DFT calculations using the B3LYP method of the singlet and triplet states, using singlet and triplet geometries, respectively.
125. Thornton, N. B.; Wojtowicz, H.; Netzel, T.; Dixon, D. W. J. Phys. Chem. B 1998, 102 (11) 2101-2110
126. Ho, S. Y.; Cheng, E. C.-C.; Tiekink, E. R. T.; Yam, V. W.-W. Inorg. Chem. 2006, 45 (20) 8165-8174