Atropisomeric 3,3′,4,4′,5,5′-Hexaferrocenyl-2,2′- bithiophene: Synthesis, solid-state structure, and electrochemistry

Organometallics

Volumn 31, Issue 5, 2012, Pages 1975-1982

  Speck, J Matthäus ^a   Schaarschmidt, Dieter ^a   Lang, Heinrich ^a  

^a CHEMNITZ UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPISOMERISM; BITHIOPHENES; BOND DISTANCE; ELECTRON DELOCALIZATION; ELECTRONIC AND STRUCTURAL PROPERTIES; FERROCENYL; H NMR SPECTROSCOPY; IN-SITU; INNER ROTATION; NEGISHI CROSS-COUPLING; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; SQUARE WAVE VOLTAMMETRY; SUPPORTING ELECTROLYTE; UV-VIS SPECTROSCOPY;

DICHLOROMETHANE; SPECTROELECTROCHEMISTRY; ULTRAVIOLET SPECTROSCOPY; ULTRAVIOLET VISIBLE SPECTROSCOPY;

X RAY DIFFRACTION;

EID: 84858141575     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om201266y     Document Type: Article

References (62)

1. Ogawa, S.; Muraoka, H.; Sato, R. Tetrahedron Lett. 2006, 47, 2479
2. Paul, F.; Goeb, S.; Justaud, F.; Argouarch, G.; Toupet, L.; Ziessel, R. F.; Lapinte, C. Inorg. Chem. 2007, 46, 9036
3. Bildstein, B.; Malaun, M.; Kopacka, H.; Fontani, M.; Zanello, P. Inorg. Chim. Acta 2000, 300-302, 16
4. Patoux, C.; Coudret, C.; Launay, J.-P.; Joachim, C.; Gourdon, A. Inorg. Chem. 1997, 36, 5037
5. Mathur, P.; Chatterjee, S.; Das, A.; Lahiri, G. K.; Maji, S.; Mobin, S. M. J. Organomet. Chem. 2007, 692, 1601
6. Packheiser, R.; Lohan, M.; Bräuer, B.; Justaud, F.; Lapinte, C.; Lang, H. J. Org. Chem. 2008, 693, 2898
7. Packheiser, R.; Ecorchard, P.; Walfort, B.; Lang, H. J. Organomet. Chem. 2008, 693, 933
8. Richardson, D. E.; Taube, H. Coord. Chem. Rev. 1984, 60, 107
9. Kaim, W.; Sarkar, B. Coord. Chem. Rev. 2007, 251, 584
10. Jones, S. C.; Barlow, S.; O'Hare, D. Chem.-Eur. J. 2005, 11, 4473
11. Barlow, S.; O'Hare, D. Chem. Rev. 1997, 97, 637
12. Bruce, I. M. Coord. Chem. Rev. 1997, 166, 91
13. Ratner, M.; Jortner, J. Molecular Electronics; Blackwell Science: Malden, MA, 1997.
14. Tour, M. J. Acc. Chem. Res. 2000, 33, 791
15. Collier, P. C.; Wong, W. E.; Belohradsky, M.; Raymo, M. F.; Stoddart, F. J.; Kuekes, J. P.; Williams, S. R.; Heath, R. J. Science 1999, 285, 391
16. Carroll, R. L.; Gorman, Ch. B. Angew. Chem., Int. Ed. 2002, 41, 4378
17. Robertson, N.; McGowan, C. A. Chem. Soc. Rev. 2003, 32, 96
18. Yu, Y; Bond, A. D.; Leonard, P. W.; Lorenz, U. J.; Timofeeva, T. V.; Vollhardt, K. P. C.; Whitener, G. D.; Yakovenko, A. A. Chem. Commun. 2006, 2572-2574
19. Diallo, A. K.; Daran, J.-C.; Varret, F.; Ruiz, J.; Astruc, D. Angew. Chem., Int. Ed. 2009, 48, 3141
20. Iyoda, M.; Kondo, T.; Okabe, T.; Matsuyama, H.; Sasaki, S.; Kuwatani, Y. Chem. Lett. 1997, 26, 35
21. Jin, B.; Tao, F.; Liu, L. J. Electroanal. Chem. 2008, 624, 179
22. Ogawa, S.; Muraoka, H.; Kikuta, K.; Saito, F.; Sato, R. J. Organomet. Chem. 2007, 692, 60
23. Kowalski, K.; Winter, R. F. J. Organomet. Chem. 2008, 693, 2181
24. Kowalski, K.; Winter, R. F. J. Organomet. Chem. 2009, 694, 1041
25. Hildebrandt, A.; Rüffer, T.; Erasmus, E.; Swarts, J. C.; Lang, H. Organometallics 2010, 29, 4900
26. Hildebrandt, A.; Schaarschmidt, D.; Lang, H. Organometallics 2011, 30, 556
27. Hildebrandt, A.; Schaarschmidt, D.; van As, L.; Swarts, J. C.; Lang, H. Inorg. Chim. Acta 2011, 374, 122
28. Hildebrandt, A.; Pfaff, U.; Lang, H. Rev. Inorg. Chem. 2011, 31, 111
29. Hildebrandt, A.; Schaarschmidt, D.; Claus, R.; Lang, H. Inorg. Chem. 2011, 50, 10623
30. Speck, J. M.; Claus, R.; Hildebrandt, A.; Rüffer, T.; Erasmus, E.; van As, L.; Swarts, J. C.; Lang, H. In preparation.
31. Hildebrandt, A.; Lang, H. Dalton Trans. 2011, 40, 11831
32. Kaleta, K.; Hildebrandt, A.; Strehler, F.; Arndt, P.; Jiao, H.; Spannenberg, A.; Lang, H.; Rosenthal, U. Angew. Chem., Int. Ed. 2011, 50, 11248
33. Clark, H. C.; Goel, A. B.; Goel, R. G.; Goel, S.; Ogini, W. O. Inorg. Chim. Acta 1978, 31, L441
34. Goel, A. B.; Goel, S. Chim. Acta 1985, 98, 67
35. Program DNMR5 by Stephenson, D. G.; Binsch, G. Quantum Chemistry Program Exchange, No 569.
36. Günther, H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry, 2 nd ed.; John Wiley & Sons: New York, 1996.
37. Standard deviation is given in parentheses.
38. Wong, W.-Y.; Lu, G.-L.; Ng, K.-F.; Choi, K.-H.; Lin, Z. J. Chem. Soc., Dalton Trans. 2001, 3250
39. Morgan, I. S.; D'Aleo, D. N.; Hudolin, M. L.; Chen, A.; Assoud, A.; Jenkins, H. A.; MacKinnon, C. D. J. Mater. Chem. 2009, 19, 8162
40. Imrie, C.; Engelbrecht, P.; Loubser, C.; McCleland, C. W.; Nyamori, V. O.; Bogardi, R.; Levendis, D. C.; Tolom, N.; van Rooyen, J.; Williams, N. J. Organomet. Chem. 2002, 645, 65
41. Smith, M. B.; March, J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 5 th ed.; Wiley: New York, 2001; p 18 ff.
42. Yu, Y.; Bond, A. D.; Leonard, P. W.; Vollhardt, K. P. C.; Whitener, G. D. Angew. Chem., Int. Ed. 2006, 45, 1794
43. Barrière, F.; Camire, N.; Geiger, W. E.; Mueller-Westerhoff, U. T.; Sanders, R. J. Am. Chem. Soc. 2002, 124, 7262
44. Barrière, F.; Geiger, W. E. J. Am. Chem. Soc. 2006, 128, 3980, and references therein
45. Gritzner, G; Kuta, J. Pure Appl. Chem. 1984, 56, 461
46. Swarts, J. C.; Nafady, A.; Roudebush, J. H.; Trupia, S.; Geiger, W. E. Inorg. Chem. 2009, 48, 2156
47. Krejčik, M.; Daněk, M.; Hartl, F. J. Electroanal. Chem. 1991, 317, 179
48. Robin, M. B.; Day, P. Adv. Inorg. Chem. Radiochem. 1967, 10, 247
49. Barlow, S. Inorg. Chem. 2001, 40, 7047
50. Caballero, A.; García, R.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2006, 72, 1161
51. Sohn, Y. S.; Hendrickson, D. N.; Gray, H. B. J. Am. Chem. Soc. 1971, 93, 3603
52. Duggan, D. E. M.; Hendrickson, D. N. Inorg. Chem. 1975, 14, 955
53. Zanello, P.; Opromolla, G.; Fabrizi de Biani, F.; Ceccanti, A.; Giorgi, G. Inorg. Chim. Acta 1997, 255, 47
54. Zhu, Y.; Wolf, M. O. Chem. Mater. 1999, 11, 2995
55. Lohan, M.; Ecorchard, P.; Rüffer, T.; Justaud, F.; Lapinte, C.; Lang, H. Organometallics 2009, 28, 1878
56. Paul, F.; Toupet, L.; Thépot, J.-Y.; Costuas, K.; Halet, J.-F.; Lapinte, C. Organometallics 2005, 24, 5464
57. Atwood, C. G.; Geiger, W. E. J. Am. Chem. Soc. 1994, 116, 10849
58. LeSuer, R. J.; Buttolph, C.; Geiger, W. E. Anal. Chem. 2004, 76, 6395
59. Fulmer, G. R.; Miller, A. J. M.; Sherden, N. H.; Gottlieb, H. E; Nudelman, A.; Stoltz, B. M.; Bercaw, J. E.; Goldberg, K. I. Organometallics 2010, 29, 2176
60. Nafady, A.; Geiger, W. E. Organometallics 2008, 27, 5624
61. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467
62. Sheldrick, G. M. SHELXL-97, Program for Crystal Structure Refinement; University of Göttingen, 1997.