Linear homobimetallic palladium complexes with end-capped SC(O)Me units

Journal of Organometallic Chemistry

Volumn 694, Issue 1, 2009, Pages 27-35

  Lang, Heinrich ^a   Döring, Katrin ^a   Taher, Deeb ^b   Siegert, Uwe ^a   Walfort, Bernhard ^a   Rüffer, Tobias ^a   Holze, Rudolf ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

^b TAFILA TECHNICAL UNIVERSITY   (Jordan)

Author keywords

Cyclic voltammetry; Nitrogen Lewis bases; Oxidative addition; Palladium; Thiol

Indexed keywords

COORDINATION REACTIONS; CYCLIC VOLTAMMETRY; PALLADIUM;

ACETYL GROUPS; BIPYRIDINE; COORDINATION GEOMETRIES; DOUBLE BONDS; ELECTROCHEMICAL REDOXES; HIGH YIELDS; NITROGEN DONORS; OXIDATIVE ADDITION; PALLADIUM COMPLEXES; SOLID STATES; THIOL;

PALLADIUM COMPOUNDS;

EID: 56649111122     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.09.031     Document Type: Article

References (125)

1. Aviram A., and Ratner M. Molecular Electronics: Science and Technology (1998), The New Academy of Science, New York
2. Martin R.E., and Diederich F. Angew. Chem., Int. Ed. Engl. 38 (1999) 1350
3. Lin H.W., Wang H., Zhao X.J., and Wang L.F.S. Synthetic Met. 135-136 (2003) 239
4. Tour J.M. Acc. Chem. Res. 33 (2000) 791 and references therein.
5. Astruc D. Acc. Chem. Res. 30 (1997) 383
6. Launay J.P. Chem. Soc. Rev. 30 (2001) 386
7. Ward M.D. Chem. Soc. Rev. 24 (1995) 121
8. Ward M.D. Chem. Ind. 15 (1996) 568
9. McClecverty J.A., and Ward M.D. Acc. Chem. Res. 31 (1998) 842
10. Tour J.M. Chem. Rev. 96 (1996) 537
11. Dudek S.P., Sikes H.D., and Chidsey C.E.D. J. Am. Chem. Soc. 123 (2001) 8033
12. Yu C.J., Chong Y., Kayyem J.F., and Gozin M. J. Org. Chem. 64 (1999) 2070
13. Hortholary C., and Coudret C. J. Org. Chem. 68 (2003) 2167
14. Skibar W., Kopacka H., Wurst K., Salzmann C., Ongania K.H., de Biani F.F., Zanello P., and Bildstein B. Organometallics 23 (2004) 1024
15. Jung D.R., and Czanderna A.W. Crit. Rev. Solid State Mater. Sci. 19 (1994) 1
16. Herdt G.C., Jung D.R., and Czanderna A.W. Prog. Surf. Sci. 50 (1995) 103
17. Tarlov M.J. Langmuir 8 (1992) 80
18. Ohgi T., Sheng H.Y., Dong Z.C., and Nejoh H. Surf. Sci. 442 (1999) 277
19. Ohgi T., Fujita D., Dong Z.C., and Nejoh H. Surf. Sci. 493 (2001) 453
20. Fisher G.L., Hooper A.E., Opila R.L., Allara D.L., and Winograd N. J. Phys. Chem. B 104 (2000) 3267
21. Konstadinidis K., Zhang P., Opila R.L., and Allara D.L. Surf. Sci. 338 (1995) 300
22. Hooper A.E., Fisher G.L., Konstadinidis K., Jung D., Nguyen H., Opila R.L., Collins R.W., Winograd N., and Allara D.L. J. Am. Chem. Soc. 121 (1999) 8052
23. Fisher G.L., Walker A.V., Hooper A.E., Tighe T.B., Bahnck K.B., Skriba H.T., Reinard M.D., Haynie B.C., Opila R.L., Winograd N., and Allara D.L. J. Am. Chem. Soc. 124 (2002) 5528
24. Carlo S.R., Wagner A.J., and Fairbrother D.H. Phys. Chem. B 104 (2000) 6633
25. Mahapatro A.K., Ying J., Ren T., and Janes D.B. Nano Lett. 8 (2008) 2131
26. Lu X., Li M., Yang C., Zhang L., Li Y., Jiang L., Li H., Jiang L., Liu C., and Hu W. Langmuir 22 (2006) 3035
27. Burtman V., Ndobe A.S., and Vardeny Z.V. J. Appl. Phys. 98 (2005) 034314
28. von Wrochem F., Scholz F., Schreiber A., Nothofer H.-G., Ford W.E., Morf P., Jung T., Yasuda A., and Wessels J.M. Langmuir 24 (2008) 6910
29. Maisch S., Buckel F., and Effenberger F. J. Am. Chem. Soc. 127 (2005) 17315
30. Zhou S.Y., Siegel D.A., Fedorov A.V., and Lanzara1 A. Phys. Rev. Lett. 101 (2008) 086402
31. Sakaguchi H., Nakamura H., Nagamura T., Ogawa T., and Matsuo T. Chem. Lett. (1989) 1715
32. Nagamura T., Sakaguchi H., and Matsuo T. Thin Solid Films 210/211 (1992) 162
33. Nakano T., Yamada Y., Matsuo T., and Yamada S. J. Phys. Chem. B 102 (1998) 8569
34. Yam V.W.W., Yang Y., Yang H.P., and Cheung K.K. Organometallics 18 (1999) 5252
35. Chu B.W.K., and Yam V.W.W. Inorg. Chem. 40 (2001) 3324
36. Willner I., Helegshabtai V., Blonder R., Katz E., and Tao G.L. J. Am. Chem. Soc. 118 (1996) 10321
37. Bumm L.A., Arnold J.J., Cygan M.T., Dunbar T.D., Burgin T.P., Jones L., Allara D.L., Tour J.M., and Weiss P.S. Science 271 (1996) 1705
38. Dudek S.P., Sikes H., and Chidsey C.E.D. J. Am. Chem. Soc. 123 (2001) 8033
39. Price W.D., and Tour J.M. Tetrahedron 59 (2003) 3131
40. Shaporenko A., Brunnbauer M., Terfort A., Johansson L.S.O., Grunze M., and Zharnikov M. Langmuir 21 (2005) 4370
41. Shaporenko A., Rößler K., Lang H., and Zharnikov M. J. Phys. Chem. B 110 (2006) 24621
42. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. Engl. 40 (2001) 486
43. Cotton F.A., Lin C., and Murillo C. Acc. Chem. Res. 34 (2001) 759
44. Tour J.M., Jones II L., Pearson D.L., Lamba J.J.S., Burgin T.P., Whitesides G.M., Allara D.L., Parikh J.A.N., and Atre S.V. J. Am. Chem. Soc. 117 (1995) 9529
45. Weiss E.A., Chiechi R.C., Kaufman G.K., Kriebel J.K., Li Z., Duati M., Rampi M.A., and Whitesides G.M. J. Am. Chem. Soc. 129 (2007) 4336
46. Paul F., and Lapinte C. Coord. Chem. Rev. 178-180 (1998) 427
47. Lang H. Angew. Chem., Int. Ed. Engl. 33 (1994) 547
48. Bunz U.H.F. Angew. Chem., Int. Ed. Engl. 35 (1996) 969
49. Ward M.D. Chem. Ind. (1997) 640
50. Swager T.M. Acc. Chem. Res. 31 (1998) 201
51. Le Narvor N., and Lapinte C. J. Chem. Soc., Chem. Commun. (1993) 357
52. Böhme U., Vogel C., Meier-Haack J., and Scheler U. J. Phys. Chem. B 111 (2007) 8344
53. Sakai N., Sisson A.L., Bürgi T., and Matile S. J. Am. Chem. Soc. 129 (2007) 15758
54. Perez-Velasco A., Gorteau V., and Matile S. Angew. Chem., Int. Ed. Engl. 47 (2008) 921
55. Bruce M.I., Costuas K., Davin T., Halet J.-F., Kramarczuk K.A., Low P.J., Nicholson B.K., Perkins G.J., Roberts R.L., Skelton B.W., Smith M.E., and White A.H. Dalton Trans. (2007) 5387
56. Cordiner R.L., Smith M.E., Batsanov A.S., Albesa-Jové D., Hartl F., Howard J.A.K., and Low P.J. Inorg. Chim. Acta 359 (2006) 946
57. Bruce M.I., Costuas K., Ellis B.G., Halet J.-F., Low P.J., Moubaraki B., Murray K.S., Ouddai N., Perkins G.J., Skelton B.W., and White A.H. Organometallics 26 (2007) 3735
58. Bruce M.I., Low P.J., Hartl F., Humphrey P.A., de Montigny F., Jevric M., Lapinte C., Perkins G.J., Roberts R.L., Skelton B.W., and White A.H. Organometallics 24 (2005) 5241
59. Fox M.A., Roberts R.L., Baines T.E., Le Guennic B., Halet J.-F., Hartl F., Yufit D.S., Albesa-Jové D., Howard J.A.K., and Low P.J. J. Am. Chem. Soc. 130 (2008) 3566
60. Brown N.J., Eckert P.K., Fox M.A., Yufit D.S., Howard J.A.K., and Low P.J. Dalton Trans. (2008) 433
61. Bruce M.I., Humphrey P.A., Jevric M., Skelton B.W., and White A.H. J. Organomet. Chem. 692 (2007) 2564
62. Kim B., Beebe J.M., Olivier C., Rigaut S., Touchard D., Kushmerick J.G., Zhu X.-Y., and Frisbie C.D. J. Phys. Chem. C 111 (2007) 7521
63. Olivier C., Kim B., Touchard D., and Rigaut S. Organometallics 27 (2008) 509
64. de Quadras L., Hampel F., and Gladysz J.A. Dalton Trans. (2006) 2929
65. Olivier C., Choua S., Turek P., Touchard D., and Rigaut S. Chem. Commun. (2007) 3100
66. Bull S.R., Palmer L.C., Fry N.J., Greenfield M.A., Messmore B.W., Meade T.J., and Stupp S.I. J. Am. Chem. Soc. 130 (2008) 2742
67. Döring K., Taher D., Walfort B., Lutz M., Spek A.L., van Klink G.P.M., Koten G.v., and Lang H. Inorg. Chim. Acta 361 (2008) 2731
68. Lang H., Rößler K., Taher D., Holze R., and Walfort B. Inorg. Chim. Acta 361 (2008) 1659
69. Taher D., Walfort B., and Lang H. Inorg. Chim. Acta 359 (2006) 1899
70. In: Socrates G. (Ed). Infrared Characteristic Group Frequencies (1980), John Wiley and Sons, Inc., New York 7
71. Maiboroda A., Rheinwald G., and Lang H. Inorg. Chem. 39 (2000) 5725
72. Maiboroda A., Fechner A., Zahn D., Hietschold M., and Lang H. Sensor. Actuat. B Chem. Sensor. 75 (2001) 188
73. Maiboroda A., and Lang H. New J. Chem. 25 (2001) 642
74. Maiboroda A., Rheinwald G., and Lang H. Inorg. Chem. Commun. 4 (2001) 381
75. Maiboroda A., Rheinwald G., and Lang H. Eur. J. Inorg. Chem. (2001) 2263
76. Maiboroda A., Rheinwald G., and Lang H. Inorg. Chim. Acta 304 (2000) 122
77. Crutchfield M.M., Dungan C.H., Letcher J.H., Mark V., and van Wazer J.R. Top. Phosphorus Chem. 5 (1963) 1
78. Song Y., Vittal J.J., Soh H., and Leung P.H. Organometallics 18 (1999) 650
79. Sakai K., Kitagawas H., Mitani T., and Yamashita M. Chem. Lett. (1997) 1237
80. Dapporto P., Sacconi L., Stoppioni P., and Zanobini F. Inorg. Chem. 20 (1981) 3834
81. Reddy K.R., Tasai W.W., Surekha K., Lee G.H., Shie-Ming J., Ting J., and Liu S.T. J. Chem. Soc., Dalton Trans. (2002) 1776
82. Allen F.H. Acta Crystallogr. B 58 (2002) 380
83. Campora J., Palma J.A.P., Valerga P., and Spillner E. Angew. Chem., Int. Ed. Engl. 38 (1999) 147
84. Hartley F.R. Organomet. Chem. Rev. A 6 (1970) 119
85. van der Voort E., van der Sluis P., and Spek A.L. Acta Crystallogr. C 43 (1987) 461
86. Vicente J., Abad J.A., Frankland A.D., and Ramírez der Arellano M.C. Chem. Eur. J. 5 (1995) 3066
87. Flemming J.P., Pilon M.C., Borbulevitch O.Y., Antipin M.Y., and Grushin V.V. Inorg. Chim. Acta 280 (1998) 87
88. Veya P., Floriani C., Chiesivilla A., and Rizzoli C. Organometallics 12 (1993) 4899
89. Vicent J., Abad J.A., Rink B., Hernández F.S., and Ramírezde Arellano M.C. Organometallics 16 (1997) 5269
90. Crociani B., Sala M., Polo A., and Bombieri G. Organometallics 5 (1986) 1369
91. Ozawa F., Sugawara M., Hasebe K., and Hayashi T. Inorg. Chim. Acta 296 (1999) 19
92. Benetollo F., Bombieri G., Dibianca F., and Crociani B. Inorg. Chim. Acta 188 (1991) 51
93. Trotter J. Acta Crystallogr. 14 (1961) 1135
94. Charbonneau G.P., and Delugeard Y. Acta Crystallogr. B 33 (1977) 1586
95. Casalone G., Gavezzotti A., and Simonetta M. J. Chem. Soc., Perkin Trans. (1973) 342
96. Boonstra E. Acta Crystallogr. 16 (1963) 816
97. Casalone G., Mariana C., Mugnoli A., and Simonetta M. Acta Crystallogr. B 25 (1969) 1741
98. Farag M.S., and Kader N.A. J. Chem. U. A. R. 3 (1960) 1
99. Manna J., Kuehl C.J., Whiteford J.A., and Stang P.J. Organometallics 16 (1997) 1897
100. Sinnokrot M.O., Valeev E.F., and Sherril C.D. J. Am. Chem. Soc. 124 (2002) 10887
101. For an introductory overview see:. Jutand A. Chem. Rev. 108 (2008) 2300
102. K. Rößler, Diploma Thesis, Chemnitz, 2005.
103. Rößler K., Rüffer T., Walfort B., Packheiser R., Holze R., Zharnikov M., and Lang H. J. Organomet. Chem. 692 (2007) 1530
104. Weidner T., Rössler K., Ecorchard P., Lang H., Grunze M., and Zharnikov M. J. Electroanal. Chem. 621 (2008) 159
105. ox,FeC = 1.16 V as reported before in Ref. [20].
106. Lash T.D., Colby D.A., Grahamur S.R., Ferrence G.M., and Szczepura L.F. Inorg. Chem. 42 (2003) 7326
107. Seligson A.L., and Trogler W.C. J. Am. Chem. Soc. 114 (1992) 7085
108. Amatore C., Azzabi M., and Jutand A. J. Am. Chem. Soc. 113 (1991) 8375
109. Campora J., Palma P., del Río D., López J.A., and Alvarez E. Organometallics 24 (2005) 3624
110. Toma S.H., Uemi M., Nikolaou S., Tomazela D.M., Eberlin M.N., and Toma H.E. Inorg. Chem. 43 (2004) 3521
111. Kaim W., Schwederski B., Dogan A., Fiedler J., Kuehl C.J., and Stang P. Inorg. Chem. 41 (2002) 4025
112. Vatsadze S., Al-Anber M., Thiel W.R., Lang H., and Holze R. J. Solid State Electrochem. 9 (2005) 764
113. Vatsadze S., Al-Anber M., Holze R., Thiel W.R., and Lang H. J. Chem. Soc., Dalton Trans. (2005) 3632
114. S. Vatsadze, M. Al-Anber, R. Holze, W. Thiel, H. Lang, Electrochemical studies and semiempirical calculations on π -conjugated dienones and related compounds, in: J. Lessard, P. Hapiot, I. Nishiguchi (Eds.), Proceedings of the Sixth International M. Baizer Award Symposium in Honor of Dennis H. Evans and Masao Tokuda - Analytical Mechanistic and Synthetic Organic Electrochemistry, The Electrochemical Society, PV 2004-10, vol. 197, Pennington, USA, 2004.
115. Jude H., Bauer J.K.B., and Connick W.B. Inorg. Chem. 43 (2004) 725
116. Jude H., Bauer J.K.B., and Connick W.B. Inorg. Chem. 41 (2002) 2275
117. Moriuchi T., Bandoh S., Kamikawa M., and Hirao T. Chem. Lett. (2000) 148
118. A conversion of given electrode potentials to the standard normal hydrogen electrode scale is possible:. Strehlow H., Knoche W., and Schneider H. Ber. Bunsenges. Phys. Chem. 77 (1973) 760
119. Gritzner G., and Kuta J. Pure Appl. Chem. 56 (1984) 461
120. Komiya S. Synthesis of Organometallic Compounds (1997), Wiley, Chichester, UK
121. Stalke D. Chem. Soc. Rev. 27 (1998) 171
122. Bruker AXS Inc., Madison, WI, USA, 1998.
123. G.M. Sheldrick, sadabs V2.01, Program for Empirical Absorption Correction of Area Detection Data, University of Göttingen, Germany, 2000.
124. Sheldrick G.M. Acta Crystallogr. Sect. A 46 (1990) 467
125. G.M. Sheldrick, shelxs 97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.