Ferrocenyl oligophenothiazines as organic-organometallic hybrid electrophores - Synthesis, structure, and electronic properties

Journal of Organometallic Chemistry

Volumn 691, Issue 3, 2006, Pages 299-308

  Sailer, Markus ^a   Rominger, Frank ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Cross coupling; Cyclic voltammetry; Ferrocenes; Heterocycles; Oligomers

Indexed keywords

CYCLIC VOLTAMMETRY; ELECTRONIC PROPERTIES; ELECTROPHORESIS; OLIGOMERS; SYNTHESIS (CHEMICAL);

CROSS-COUPLING; FERROCENES; HETEROCYCLES;

ORGANOMETALLICS;

EID: 29444461451     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.08.012     Document Type: Article

References (89)

1. For recent reviews, see e.g. J.M. Seminario Nature Mater. 4 2005 111
2. A.H. Flood, J.F. Stoddardt, D.W. Steuerman, and J.R. Heath Science 306 2004 2055
3. G. Maruccio, R. Cingolani, and R. Rinaldi J. Mater. Chem. 14 2004 542
4. N. Robertson, and C.A. McGowan Chem. Soc. Rev. 32 2003 96
5. R.L. Carroll, and C.B. Gorman Angew. Chem. Int. Ed. 41 2002 4378
6. D. Astruc Acc. Chem. Res. 30 1997 383
7. L. Oriol, and J. Serrano Adv. Mater. 7 1995 348
8. N.G. Connelly, and W.E. Geiger Adv. Organomet. Chem. 23 1984 1
9. N.G. Connelly, and W.E. Geiger Adv. Organomet. Chem. 24 1985 87
10. I. Manners Angew. Chem., Int. Ed. Engl. 35 1996 1602
11. U.H.F. Bunz Angew. Chem., Int. Ed. Engl. 35 1996 968
12. P. Nguyen, P. Gómez-Elipe, and I. Manners Chem. Rev. 99 1999 1515
13. V.W.-W. Yam, K.K.-W. Lo, and K.M.-C. Wong J. Organomet. Chem. 578 1999 3
14. E. Antonelli, P. Rosi, C. Lo Sterzo, and E. Viola J. Organomet. Chem. 578 1999 210
15. For reviews on organometallic NLO chromophores see, e.g. I.R. Whittall, A.M. McDonagh, M.G. Humphrey, and M. Samoc Adv. Organomet. Chem. 42 1998 291
16. I.R. Whittall, A.M. McDonagh, M.G. Humphrey, and M. Samoc Adv. Organomet. Chem. 43 1998 349
17. N.J. Long Angew. Chem., Int. Ed. Engl. 34 1995 6
18. S.R. Marder, and J.W. Perry Adv. Mater. 5 1993 804
19. W. Nie Adv. Mater. 5 1993 520
20. D.R. Kanis, M.A. Ratner, and T.J. Marks Chem. Rev. 94 1994 195
21. For representative novel organometallic NLO chromophores see, e.g. U. Behrens, H. Brussaard, U. Hagenau, J. Heck, E. Hendrickx, J. Körnich, J.G.M. van der Linden, A. Persoons, A.L. Spek, N. Veldman, B. Voss, and H. Wong Chem. Eur. J. 2 1996 98
22. C. Dhenaut, I. Ledoux, I.D.W. Samuel, J. Zyss, M. Bourgault, and H. Le Bozec Nature 374 1995 339
23. M. Tamm, A. Grzegorzeweski, T. Steiner, T. Jentzsch, and W. Werncke Organometallics 15 1996 4984
24. I.R. Whittall, M.G. Humphrey, S. Houbrechts, A. Persoons, and D.C.R. Hockless Organometallics 15 1996 5738
25. I.R. Whittall, M.P. Cifuentes, M.G. Humphrey, B. Luther-Davies, M. Samoc, S. Houbrechts, A. Persoons, G.A. Heath, and D.C.R. Hockless J. Organomet. Chem. 549 1997 127
26. T.J.J. Müller, A. Netz, M. Ansorge, E. Schmälzlin, C. Bräuchle, and K. Meerholz Organometallics 18 1999 5066
27. For reviews on hybrids of ferrocenes and functional π-systems, see e.g. E. Nakamura Pure Appl. Chem. 75 2003 427
28. H. Korri-Youssoufi, and B. Makrouf Anal. Chim. Acta 469 2002 85
29. For reviews on organic-inorganic hybrid polymers and hybrid materials, see e.g. M. Rehahn A.-D. Schlüter Synthesis of Polymers Materials Science and Technology Series vol. 20 1999 Wiley-VCH Weinheim 319
30. G. Cerveau, R.J.P. Corriu, and N. Costa J. Non-Cryst. Solids 163 1993 226
31. M. Scherer, J.L. Sessler, M. Moini, A. Gebauer, and V. Lynch Chem. Eur. J. 4 1998 152
32. For conjugated ferrocenyl oligomers, see e.g. E. Peris Coord. Chem. Rev. 248 2004 279
33. H. Nishihara Adv. Inorg. Chem. 53 2002 41
34. G.E. Southard, and M.D. Curtis Synthesis 2002 1177
35. A. Peruga, J.A. Mata, D. Sainz, and E. Peris J. Organomet. Chem. 637-639 2001 191
36. H. Nishihara Bull. Chem. Soc. Jpn. 74 2001 19
37. T. Horikoshi, K. Kubo, and H. Nishihara J. Chem. Soc., Dalton Trans. 19 1999 3355
38. N.J. Long, A.J. Martin, R. Vilar, A.J.P. White, D.J. Williams, and M. Younus Organometallics 18 1999 4261
39. For conjugated ferrocenyl polymers, see e.g. R.W. Heo, J.-S. Park, and T.R. Lee Macromolecules 38 2005 2564
40. M. Murata, H. Nishihara, in: Macromolecules Containing Metal and Metal-Like Elements, vol. 2, 2004, p. 135.
41. R.W. Heo, J.-S. Park, J.T. Goodson, G.C. Claudio, M. Takenaga, T.A. Albright, and T.R. Lee Tetrahedron 60 2004 7225
42. T. Yasuda, J. Abe, H. Yoshida, T. Iyoda, and T. Kawai Adv. Synth. Catal. 344 2002 705
43. T. Morikita, and T. Yamamoto J. Organomet. Chem. 637-639 2001 809
44. H. Plenio, J. Hermann, and A. Sehring Chem. Eur. J. 6 2000 1820
45. S.J. Higgins, C.L. Jones, and S.M. Francis Synth. Met. 98 1998 2110
46. T. Yamamoto, T. Morikita, T. Maruyama, K. Kubota, and M. Katada Macromolecules 30 1997 5390
47. M. Bochmann, J. Lu, and R.D. Cannon J. Organomet. Chem. 518 1996 97
48. B.M. Foxman, D.A. Gronbeck, and M. Rosenblum J. Organomet. Chem. 412 1991 287
49. For electronic communication in ferrocenes-based oligometallic systems, see e.g. M. Scheibitz, J.B. Heilmann, R.F. Winter, M. Bolte, J.W. Bats, and M. Wagner Dalton Trans. 2005 159
50. S. Guo, F. Peters, F. Fabrizi de Biani, J.W. Bats, E. Herdtweck, P. Zanello, and M. Wagner Inorg. Chem. 40 2001 4928
51. L. Ding, K. Ma, F. Fabrizi de Biani, M. Bolte, P. Zanello, and M. Wagner Organometallics 20 2001 1041
52. S. Barlow, and S.R. Marder Chem. Commun. 2000 1555
53. M. Grosche, E. Herdtweck, F. Peters, and M. Wagner Organometallics 18 1999 4669
54. U.H.F. Bunz, G. Roidl, M. Altmann, V. Enkelmann, and K.D. Shimizu J. Am. Chem. Soc. 121 1999 10719
55. W. Skibar, H. Kopacka, K. Wurst, C. Salzmann, K.-H. Ongania, F. Fabrizi de Biani, P. Zanello, and B. Bildstein Organometallics 23 2004 1024
56. S.A. Getty, C. Engtrakul, L. Wang, R. Liu, S.-H. Ke, H.U. Baranger, W. Yang, M.S. Fuhrer, and L.R. Sita Condensed Matter 2004 1 see also: http://xxx.lanl.gov/pdf/cond-mat/0409433
57. C. Hortholary, and C. Coudret J. Org. Chem. 68 2003 2167
58. Y. Zhu, and M.O. Wolf J. Am. Chem. Soc. 122 2000 10121
59. C.J. Yu, Y. Chong, J.F. Kayyem, and M. Gozin J. Org. Chem. 64 1999 2070
60. A. Hradsky, B. Bildstein, N. Schuler, H. Schottenberger, P. Jaitner, K.-H. Ongania, K. Wurst, and J.-P. Launay Organometallics 16 1997 392
61. A.E.-W. Sarhan, Y. Nouchi, and T. Izumi Tetrahedron 59 2003 6353
62. A.E.-W.A.O. Sarhan, M. Murakami, and T. Izumi Monatsh. Chem. 133 2002 1055
63. A. Gonzalez-Cabello, P. Vazquez, and T. Torres J. Organomet. Chem. 637-639 2001 751
64. S.-G. Liu, I. Perez, N. Martin, and L. Echegoyen J. Org. Chem. 65 2000 9092
65. For a Fc-polymer with two different redox centers, see e.g. K. Naka, T. Uemura, and Y. Chujo Macromolecules 33 2000 6965
66. T.J. Zimmermann, and T.J.J. Müller Synthesis 2002 1157
67. C.S. Krämer, K. Zeitler, and T.J.J. Müller Tetrahedron Lett. 42 2001 8619
68. C.S. Krämer, and T.J.J. Müller Eur. J. Org. Chem. 2003 3534
69. M. Sailer, R.-A. Gropeanu, and T.J.J. Müller J. Org. Chem. 68 2003 7509
70. C.S. Krämer, T.J. Zimmermann, M. Sailer, and T.J.J. Müller Synthesis 2002 1163
71. T.J. Zimmermann, and T.J.J. Müller Eur. J. Org. Chem. 2002 2269
72. T.J. Zimmermann, O. Freundel, R. Gompper, and T.J.J. Müller Eur. J. Org. Chem. 2000 3305
73. C.S. Krämer, K. Zeitler, and T.J.J. Müller Org. Lett. 2 2000 3723
74. T.J.J. Müller Tetrahedron Lett. 40 1999 6563
75. For Pd-catalyzed arylation of ferrocene diboronic acid, see e.g. R. Knapp, and M. Rehahn J. Organomet. Chem. 452 1993 235
76. C. Imrie, C. Loubser, P. Engelbrecht, and C.W. McCleland J. Chem. Soc., Perkin Trans. 1 1999 2513
77. For the presence and the absence of π-stacking in 1,1′- diarylferrocenes, see e.g. U. Siemeling, U. Vorfeld, B. Neumann, H.-G. Stammler, M. Fontani, and P. Zanello J. Organomet. Chem. 637-639 2001 733
78. M.D. Blanchard, R.P. Hughes, T.E. Concolino, and A.L. Rheingold Chem. Mater. 12 2000 1604
79. I.R. Butler, L.J. Hobson, S.J. Coles, M.B. Hursthouse, and K.M. Abdul Malik J. Organomet. Chem. 540 1997 27
80. F. Gelin, and R.P. Thummel J. Org. Chem. 57 1992 3780
81. As implemented in PC spartan 02, Wavefunction Inc., Irvine, CA, 2002.
82. Applying BP (Becke, Perdew) G-31** non-local density functionals as implemented in PC spartan 02, Wavefunction Inc., Irvine, CA, 2002.
83. A. Haaland, and J.E. Nilsson Acta Chem. Scand. 22 1968 2653
84. P. Zanello A. Togni T. Hayashi Ferrocenes 1995 VCH Weinheim, New York, Basel, Cambridge, Tokyo 317
85. Applying BP (Becke, Perdew) G-31* non-local density functionals as implemented in PC spartan 02, Wavefunction Inc., Irvine, CA, 2002.
86. H.G.O. Becker, W. Berger, G. Domschke, E. Fanghänel, J. Faust, M. Fischer, F. Gentz, K. Gewald, R. Gluch, R. Mayer, K. Müller, D. Pavel, H. Schmidt, K. Schollberg, K. Schwetlick, E. Seiler, and G. Zeppenfeld Organikum 20th ed. 1996 Johann Ambrosius Barth Verlag Heidelberg, Leipzig
87. I.R. Butler, S.B. Wilkes, S.J. Mcdonald, L.J. Hobson, A. Taralp, and C.P. Wilde Polyhedron 12 1993 129
88. G.M. Sheldrick, Program sadabs V2.03 for absorption correction, Bruker Analytical X-ray-Division, Madison, WI, 2001.
89. G.M. Sheldrick, Software package shelxtl V6.12 for structure solution and refinement, Bruker Analytical X-ray-Division, Madison, WI, 2000.