The effect of thiophene ring substitution position on the properties and electrochemical behaviour of alkyne-dicobaltcarbonylthiophene complexes

Journal of Organometallic Chemistry

Volumn 693, Issue 23, 2008, Pages 3457-3470

  Arnanz, Avelina ^a   Marcos, María Luisa ^a   Delgado, Salomé ^a   González Velasco, Jaime ^a   Moreno, Consuelo ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Carbonylcobalt complexes; Electrochemistry; Thiophene

Indexed keywords

ACETYLENE; ELECTROCHEMICAL PROPERTIES; THIOPHENE;

CARBONYLCOBALT COMPLEXES; ELECTROCHEMICAL BEHAVIOUR; ELECTROCHEMISTRY; THIOPHENE RINGS;

ORGANIC POLYMERS;

EID: 53349103142     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.08.005     Document Type: Article

References (105)

1. Nast R. Coord. Chem. Rev. 47 (1982) 89-124
2. Ward M.D. Chem. Soc. Rev. 24 (1995) 121-134
3. Paul F., and Lapinte C. Coord. Chem. Rev. 431-509 (1998) 178-180
4. Bunz U.H.F. J. Organomet. Chem. 683 (2003) 267-445
5. Kaim W., and Lahiri G.K. Angew. Chem., Int. Ed. 46 (2007) 1778-1796 and references therein
6. Hahn R.A., and Bloor D. Organic Materials for Non-Linear Optics (1989), The Royal Society of Chemistry, London
7. Stuchky G.D., Marder S.R., and Sohn J. Materials for Nonlinear Optics; Chemical Perspectives (1991), American Chemical Society, Washington, DC
8. Marder S.R. In: Bruce D.W., and O'Hare D. (Eds). Inorganic Materials (1996), Wiley, Chichester 121
9. Haller M., Luo J., Li H., Kim T.-D., Liao Y., Robinson B.H., Dalton L.R., and Jen A.K.-Y. Macromolecules 37 (2004) 688-690
10. Nielsen R.D., Rommel H.L., and Robinson B.H. J. Phys. Chem. B 108 (2004) 8659-8667
11. Cifuentes M.P., Humphrey M.G., Morrall J.P., Samoc M., Paul F., Lapinte C., and Roisnel T. Organometallics 24 (2005) 4280-4288
12. Senge M.O., Fazekas M., Notaras E.G.A., Blau W.J., Zawadzka M., Locos O.B., and Ni Mhuircheartaigh E.M. Adv. Mater. 19 (2007) 2737-2774
13. Zhou G.-J., Wong W.-Y., Ye C., and Lin Z. Adv. Funct. Mater. 17 (2007) 963-975
14. Frapper G., and Kertesz M. Inorg. Chem. 32 (1993) 732-740
15. Low P.J. The Roy. Soc. Chem., Dalton Trans. (2005) 2821-2824
16. Green M.L.H., Marder S.R., Thomson M.E., Bandy J.A., Bloor D., Kolinsky P.V., and Jones R.J. Nature 330 (1987) 360-362
17. Miller J.S., and Epstein A.J. Angew. Chem., Int. Ed. 33 (1994) 385-415
18. Khan M.S., Al-Mandhary M.R.A., Al-Suti M.K., Ahrens B., Mahon M.F., Male L., Raithby P.R., Boothby C.E., and Koehler A. J. Chem. Soc., Dalton Trans. (2003) 74-84
19. Yam V.W.-W., Wong K.M.-C., and Zhu N. Angew. Chem., Int. Ed. 42 (2003) 1400-1403
20. Li P., Ahrens B., Feeder N., Raithby P.R., Teat S.J., and Khan M.S. J. Chem. Soc., Dalton Trans. (2005) 874-883
21. Wong W.-Y. J. Chem. Soc., Dalton Trans. (2007) 4495-4510
22. Dosa P.I., Erben C., Iyer V.S., Vollhardt K.P.C., and Wasser I.M. J. Am. Chem. Soc. 121 (1999) 10430-10431
23. McQuade D.T., Pullen A.E., and Swager T.M. Chem. Rev. 100 (2000) 2537-2574
24. Robertson N., and McGowan C.A. Chem. Soc. Rev. 32 (2003) 96-103
25. Elsevier C.J., Reedijk J., Walton P.H., and Ward M.D. J. Chem. Soc., Dalton Trans. (2003) 1869-1880
26. Stahl J., Bohling J., James C., Bauer E.B., Eike B., Peters T.B., Mohr W., Martin-Alvarez J.M., Hampel F., Gladysz J.A., and John A. Angew. Chem., Int. Ed. 41 (2002) 1871-1876
27. De Quadras L., Bauer E.B., Mohr W., Bohling J.C., Peters T.B., Martin-Alvarez J.M., Hampel F., and Gladysz J.A. J. Am. Chem. Soc. 129 (2007) 8296-8309
28. Molecular and biomolecular electronics. In: Birge R.R. (Ed). Advances in Chemistry Series 240 (1994), American Chemical Society
29. In: Kirk W.P., and Reed M.A. (Eds). Nanostructures and Mesoscopic Systems (1992), Academic, New York
30. Molecular electronics: science and technology. In: Aviram A. (Ed). Conference Proceedings No. 262 (1992), American Institute of Physics, New York
31. Astruc D. Electron Transfer and Radical Processes in Transition-Metal Chemistry (1995), VCH Publishers, New York
32. Andres R.P., Bielefeld J.D., Henderson J.I., Janes D.B., Kolagunta V.R., Kubiak C.P., Mahoney W.J., and Osifchin R.G. Science 273 (1996) 1690-1693
33. Feldheim D.L., and Keating C.D. Chem. Soc. Rev. 27 (1998) 1-12
34. Adams R.D., Qu B., and Smith M.D. Inorg. Chem. 40 (2001) 2932-2934
35. Bruce M.I., Costuas K., Halet J.-F., May B.C., Low P.J., Nicholson B.K., Skelton B.W., and White A.H. J. Chem. Soc., Dalton Trans. (2002) 383-398
36. Yao H., Sabat M., Grimes R.N., Fabrizi de Biani F., and Zanello P. Angew. Chem., Int. Ed. 42 (2003) 1002-1005
37. Yao H., Sabat M., Grimes R.N., Zanello P., and Fabrizi de Biani F. Organometallics 22 (2003) 2581-2593
38. Tanifuji N., Matsuda K., and Irie M. Mol. Cryst. Liq. Cryst. 430 (2005) 75-79
39. Roncali J. Chem. Rev. 92 (1992) 711-738
40. Caballero A., Tárraga A., Velasco M.D., and Molina P. J. Chem. Soc., Dalton Trans. (2006) 1390-1398
41. Robinson B.H., and Simpson J. In: Chanon M. (Ed). Paramagnetic Organometallic Species in Activation: Selectivity Catalysis (1989), Kluwer, Dordrecht 357
42. Roncali J. Chem. Rev. 97 (1997) 173-205
43. Adams R.D., and Qu B. Organometallics 19 (2000) 2411-2413
44. Jiao H., and Gladysz J.A. New J. Chem. 25 (2001) 551-562
45. Moreno C., Marcos M.L., Domínguez G., Arnanz A., Farrar D.H., Teeple R., Lough A., González-Velasco J., and Delgado S. J. Organomet. Chem. 631 (2001) 19-28
46. Marcos M.L., Macazaga M.J., Medina R.M., Moreno C., Castro J.A., Gómez J.L., Delgado S., and González-Velasco J. Inorg. Chim. Acta 312 (2001) 249-255
47. Ceccon A., Santi S., Orian L., and Bisello A. Coord. Chem. Rev. 248 (2004) 683-724
48. Le Narvor N., Toupet L., and Lapinte C. J. Am. Chem. Soc. 117 (1995) 7129-7138
49. Bartik T., Bartik B., Brady M., Dembinski R., and Gladysz J.A. Angew. Chem., Int. Ed. 35 (1996) 414-417
50. Coat F., and Lapinte C. Organometallics 15 (1996) 477-479
51. Jung T.S., Kim J.H., Jang E.K., Kim D.H., Sim Y.-B., Park B., and Shin S.C. J. Organomet. Chem. 599 (2000) 232-237
52. Medina R.M., Moreno C., Marcos M.L., Castro J.A., Benito F., Arnanz A., Delgado S., González-Velasco J., and Macazaga M.J. Inorg. Chim. Acta 357 (2004) 2069-2080
53. Arnanz A., Marcos M.L., Moreno C., Farrar D.H., Lough A.J., Yu J.O., Delgado S., and González-Velasco J. J. Organomet. Chem. 689 (2004) 3218-3231
54. Arnanz A., Moreno C., Marcos M.L., González-Velasco J., and Delgado S. Eur. J. Inorg. Chem. (2007) 5215-5225
55. Sugihara Y., Yagi T., Murata I., and Imamura A. J. Am. Chem. Soc. 114 (1992) 1479-1481
56. Sugihara Y., Miyatake R., and Yagi T. Chem. Lett. (1993) 933-936
57. Sahu B., Namboothiri I.N.N., and Persky R. Tetrahedron Lett. 46 (2005) 2593-2597
58. Perrin D.D., Armarego S.L.F., and Perrin D.R. Purification of Laboratory Chemicals (1980), Pergamon Press, New York
59. Cotton F.A. Inorg. Synth. 13 (1972) 121
60. Coulson D.R. Inorg. Synth. (Reagents Transition Met. Complex Organomet. Synth.) 28 (1990) 107-109
61. Noeth V.H., Meinel L., and Anorg Z. Allg. Chem. 349 (1967) 225-240
62. smart v. 5.625, Area-Detector Software Package, Bruker AXS, Madison, WI, 2001.
63. Bruker axs shelxtl version 6.10, Structure Determination Package, Bruker AXS, Madison, WI, 2000.
64. Mariden J.A., and Haley M.M. Cross-coupling reactions to sp carbon atoms. In: de Meijere A., and Diederich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley, Weinheim 318-345
65. Brandsma L., and Verkruijsse H.D. Synth. Commun. 20 (1990) 2275-2277
66. Dana B.H., Robinson B.H., and Simpson J. J. Organomet. Chem. 648 (2002) 251-269
67. Fringuelli F., Marino G., Taticchi A., and Grandolini G. J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. 4 (1974) 332-337
68. Lewis J., Long N.J., Raithby P.R., Shields G.P., Wong W.-Y., and Younus M. J. Chem. Soc., Dalton Trans. (1997) 4283-4288
69. Sakar A., and Haley M.M. Chem. Commun. (2000) 1733-1734
70. Colbert M.C.B., Ingham S.L., Nicholas J.L., Long N.J., and Raithby P.R. J. Chem. Soc., Dalton Trans. (1994) 2215-2216
71. Jutzi P., and Kleinebekel B. J. Organomet. Chem. 545 (1997) 573-576
72. Guldi D.M., Maggini M., Scorrano G., and Prato M. J. Am. Chem. Soc. 119 (1997) 974-980
73. Draper S.M., Delamesiere M., Champeil E., Twamley B., Byrne J.J., and Long C. J. Organomet. Chem. 589 (1999) 157-167
74. Bor G. Spectrochim. Acta 19 (1963) 1209-1224
75. Nicholas K.M., Nestle M.O., and Seyferth D. In: Alper H. (Ed). Transition Metal Organometallics in Organic Synthesis vol. 2 (1978), Academic Press, New York 2
76. Davison J.L. In: Braterman P.S. (Ed). Reactions of Coordinated Ligands vol. I (1986), Plenum Press, New York 825
77. Lewis J., Lin B., Khan M.S., Al-Mandhary M.R.A., and Raithby P.R. J. Organomet. Chem. 484 (1994) 161-167
78. Wong W.-Y., Lam H.-Y., and Lee S.-M. J. Organomet. Chem. 648 (2000) 70-80
79. R.S. Dickinson, P.J. Fraser, in: F.G.A. Stone, R. West (Eds.), Advances in Organometallic Chemistry, vol. 12, 1974, pp. 323-377
80. Diederich F., Rubin Y., Chapman O.L., and Goroff N.S. Helv. Chim. Acta 77 (1994) 1441-1457
81. Happ B., Bartik T., Zucchi C., Rossi M.C., Ghelfi F., Pályi G., Váradi G., Szalontai G., Horváth I.T., Chiesi-Villa A., and Guastini C. Organometallics 14 (1995) 809-819
82. Cetini G., Gambino O., Rosetti R., and Sappa E. J. Organomet. Chem. 8 (1967) 149-154
83. Housecroft C.E., Johnson B.F.G., Khan M.S., Lewis J., Raithby P.R., Robson M.E., and Wilkinson D.A. J. Chem. Soc., Dalton Trans. (1992) 3171-3178
84. Aime S., Milone L., Rossetti R., and Stanghellini P.L. Inorg. Chim. Acta 22 (1977) 135-139
85. Harris R.K. Nuclear Magnetic Resonance Spectroscopy: A Physiochemical View (1983), Pitman, London
86. Castro J., Moyano A., Pericas M.A., Riera A., Maestro M.A., and Mahía J. Organometallics 19 (2000) 1704-1712
87. Snaith T.J., Low P.J., Rousseau R., Pushmann H., and Howard J.A.K. J. Chem. Soc., Dalton Trans. (2001) 292-299
88. Champeil E., and Draper S.M.J. Chem. Soc., Dalton Trans. (2001) 1440-1447
89. Lang H., Lay U., and Weinmann M. J. Organomet. Chem. 436 (1992) 265-276
90. Bartik T., Happ B., Iglewsky M., Badmann H., Boese R., Heimbach P., Hoffmann T., and Wenschuh E. Organometallics 11 (1992) 1235-1241
91. Jeffery J.C., Pereira R.M.S., Vargas M.D., and Went M.J. J. Chem. Soc., Dalton Trans. (1995) 1805-1811 and references therein
92. Bruce M.I., Kelly B.D., Skelton B.W., and White A.H. J. Chem. Soc., Dalton Trans. (1999) 847-852
93. Sumner G.G., Klug H.P., and Alexander L.E. Acta Crystallogr. 17 (1964) 732-742
94. Weng W., Bartik T., Brady M., Bartik B., Ramsden J.A., Arif A.M., and Gladysz J.A. J. Am. Chem. Soc. 117 (1995) 11922-11931
95. Bartik B., Dembinski R., Bartik T., Arif A.M., and Gladysz J.A. New J. Chem. 21 (1997) 739-750
96. Brady M., Weng W., Zhou Y., Seyler J.W., Amoroso A.J., Arif A.M., Boehme M., Frenking G., and Gladysz J.A. J. Am. Chem. Soc. 119 (1997) 775-788
97. Moreno C., Gómez J.L., Medina R.-M., Macazaga M.-J., Arnanz A., Lough A., Farrar D.H., and Delgado S. J. Organomet. Chem. 579 (1999) 63-74
98. Bezems G.J., Rieger P.H., and Visco S.J. J. Chem. Soc., Chem. Commun. (1981) 265-266
99. Arewgoda C.M., Rieger P.H., Robinson B.H., Simpson J., and Visco S.J. J. Am. Chem. Soc. 104 (1982) 5633-5640
100. Osella D., and Fiedler J. Organometallics 11 (1992) 3875-3878
101. Osella D., Milone L., Nervi C., and Ravera M. J. Organomet. Chem. 488 (1995) 1-7
102. Duffy N.W., McAdam J., Nervi C., Osella D., Ravera M., Robinson B.H., and Simpson J. Inorg. Chim. Acta 247 (1996) 99-104
103. Osella D., Milone L., Nervi C., and Ravera M. Eur. J. Inorg. Chem. (1998) 1473-1477
104. Sowa J.R., and Angelici R.J. Inorg. Chem. 30 (1991) 3534-3537
105. Bard A.J., and Faulkner L.R. Electrochemical Methods: Fundamentals and Applications. 2nd ed. (2001), Wiley, New York p. 505