Optically and redox-active ferroceneacetylene polymers and oligomers

Chemistry - A European Journal

Volumn 6, Issue 10, 2000, Pages 1820-1829

  Plenio, Herbert ^a   Hermann, Jörg ^b   Sehring, Alexander ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Acetylenes; Ferrocene; Optical activity; Polymers; Redox properties

Indexed keywords

ACETYLENE; OLIGOMER; POLYMER;

ARTICLE; CATALYSIS; OPTICAL ROTATION; OXIDATION REDUCTION REACTION; REACTION ANALYSIS;

EID: 0034659865     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000515)6:10<1820::aid-chem1820>3.0.co;2-a     Document Type: Article

References (77)

1. Comprehensive Polymer Science (Ed.-in-Chief: G. Allen), Pergamon, Oxford, 1989-1996.
2. a) F. Ciardelli, E. Tsuchida, D. Wöhrle, Macromolecule-Metal Complexes, Springer, Berlin, 1996;
3. b) M. Rehahn, Acta Polym. 1998, 49, 201.
4. a) J. Roncali, Chem. Rev. 1997, 97, 173;
5. b) P. Novak, K. Müller, K. S. V. Santhanam, O. Haas, Chem. Rev. 1997, 97, 207.
6. a) Inorganic and Organometallic Polymers, ACS Symp. Ser. 360, American Chemical Society, Washington DC, 1988;
7. b) Inorganic and Organometallic Polymers II, ACS Symp. Ser. 572, American Chemical Society, Washington DC, 1994;
8. c) Inorganic and Organometallic Oligomers and Polymers (Eds.: R. M. Laine, J. F. Harrod), Kluwer, Amsterdam, 1991.
9. T. J. Peckham, P. Gómez-Elipe, I. Manners, in Metallocenes (Eds.: A. Togni, R. L. Haltermann), p. 723, Wiley-VCH, Weinheim, 1998.
10. a) I. Manners, Can. J. Chem. 1998, 76, 371;
11. b) I. Manners, Angew. Chem. 1996, 108, 1713; Angew. Chem. Int. Ed. Engl. 1996, 35, 1602;
12. b) I. Manners, Angew. Chem. 1996, 108, 1713; Angew. Chem. Int. Ed. Engl. 1996, 35, 1602;
13. c) P. Nguyen, P. Elipe-Gomez, I. Manners, Chem. Rev. 1999, 99, 1515.
14. a) R. Knapp, U. Velten, M. Rehahn, Polymer 1998, 39, 5827;
15. b) A. S. Gamble, J. T. Patton, J. M. Boncella, Makromol. Chem. Rapid Commun. 1993, 13, 109;
16. c) O. Lavastre, M. Even, P. H. Dixneuf, A. Pacreau, J.-P. Vairon, Organometallics 1996, 15, 1530;
17. d) C. E. Stanton, T. R. Lee, R. H. Grubbs, N. S. Lewis, J. K. Pudelski, M. R. Callstrom, M. S. Erickson, M. L. McLaughlin, Macromolecules 1995, 28, 8713;
18. e) M. A. Buretea, T. D. Tilley, Organometallics 1997, 16, 1507;
19. f) T. Yamamoto, T. Moritaka, T. Maruyama, K. Kubota, M. Katada, Macromolecules 1997, 30, 5390;
20. g) R. Bayer, T. Pöhlmann, O. Nuyken, Makromol. Chem. Rapid Commun. 1993, 14, 359;
21. h) R. S. Hsung, C. E. D. Chidsey, L. R. Sita, Organometallics 1995, 14, 4808.
22. a) T. Hirao, M. Kurashina, K. Aramaki, H. Nishihara, J. Chem. Soc. Dalton Trans. 1996, 2929, and references therein;
23. b) E. W. Neuse, L. Bednarik, Macromolecules 1979, 12, 187.
24. a) T. Morikita, T. Maruyama, T. Yamamoto, K. Kubota, M. Katada, Inorg. Chim. Acta 1998, 269, 310;
25. b) R. W. Heo, F. B. Somoza, T. Randall, J. Am. Chem. Soc. 1998, 120, 1621;
26. c) T. Yamamoto, T. Morikita, T. Maruyama, K. Kubota, M. Katada, Macromolecules 1997, 30, 5390;
27. d) M. R. Buchmeiser, N. Schuler, G. Kaltenhauser, K. H. Ongania, I. Lagoja, K. Wurst, H. Schottenberger, Macromolecules 1998, 31, 3175.
28. a) K. Müllen, G. Wegner, Conducting Polymers. The Oligomer Approach, VCH-Wiley, Weinheim, 1998;
29. b) R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440; Angew. Chem. Int. Ed. 1999, 38, 1350.
30. b) R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440; Angew. Chem. Int. Ed. 1999, 38, 1350.
31. F. Paul, C. Lapinte, Coord. Chem. Rev. 1998, 178-180, 431.
32. a) S. Creager, C. J. Yu, C. Bamdad, S. O'Connor, T. MacLean, E. Lam, Y. Chong, G. T. Olsen, J. Luo, M. Gozin, J. F. Kayyem, J. Am. Chem. Soc. 1999, 121, 1059;
33. b) A. Hradsky, B. Bildstein, N. Schuler, H. Schottenberger, P. Jaitner, K.-H. Ogania, K. Wurst. J.-P. Launay, Organometallics 1997, 16, 392.
34. R. P. Kingsborough, T. M. Swager, Prog. Inorg. Chem. 1999, 48, 123.
35. a) U. H. F. Bunz, Y. Rubin, Y. Tobe, Chem. Soc. Rev. 1999, 28, 107;
36. b) M. Altmann, J. Friedrich, F. Beer, R. Reuter, V. Enkelmann, U. H. F. Bunz, J. Am. Chem. Soc. 1997, 119, 1472;
37. c) S. Setayesh, U. H. F. Bunz, Organometallics 1996, 15, 5470;
38. d) U. H. F. Bunz in Carbon Rich Compounds II (Ed.: A. de Meijere), Topics in Current Chemistry, Vol. 201, Springer, Berlin, 1999;
39. e) M. Altmann, U. H. F. Bunz, Angew. Chem. 1995, 107, 603; Angew. Chem. Int. Ed. Engl. 1995, 34, 569.
40. e) M. Altmann, U. H. F. Bunz, Angew. Chem. 1995, 107, 603; Angew. Chem. Int. Ed. Engl. 1995, 34, 569.
41. H. Plenio, J. Hermann, J. Leukel, Eur. J. Inorg. Chem. 1998, 2063.
42. a) R. Giesa, J. Macromol. Sci. Rev. Macromol. Chem. Phys. 1996, C36, 631;
43. b) C. J. Li, W. T. Slaven, Y. P. Chen, V. T. John, S. H. Rachakonda, Chem. Commun. 1998, 1351;
44. c) L. Kloppenburg, D. Song, U. H. F. Bunz. J. Am. Chem. Soc. 1998, 120, 7973.
45. T. Yamamoto, M. Takagi, K. Kizu, T. Maruyama, K. Kubota, H. Kanbara, T. Kurihara, T. Kaino, Chem. Commun. 1993, 797.
46. a) C. E. Halkyard, M. E. Rampey, L. Kloppenburg, S. L. Studer-Martinez, U. H. F. Bunz, Macromolecules 1998, 31, 8655;
47. b) M. Moroni, J. LeMoigne, T. A. Pham, J.-Y. Bigot, Macromolecules 1997, 30, 1964.
48. O. Riant, O. Samuel, T. Flessner, S. Taudien, H. B. Kagan, J. Org. Chem. 1997, 62, 6733.
49. a) J. B. Campbell in Organocopper Reagents (Ed.: R. J. K. Taylor), Oxford University Press, Oxford, 1994, ch. 10;
50. b) J. Tsuji, Pd Reagents and Catalysts, John Wiley, Chichester, 1995.
51. a) C. G. Cameron, P. G. Pickup, J. Am. Chem. Soc. 1999, 121, 7710;
52. b) S. S. Zhu, T. M. Swager, J. Am. Chem. Soc. 1997, 119, 1172.
53. Z. Peng, A. R. Gharavi, L. Yu, J. Am. Chem. Soc. 1997, 119, 4622.
54. H. Plenio, M. Sanz, unpublished results.
55. J. Zhang, D. J. Pesak, J. L. Ludwick, J. S. Moore, J. Am. Chem. Soc. 1994, 116, 4227.
56. J. M. Tour, Chem. Rev. 1996, 96, 537.
57. V. Snieckus, Chem. Rev. 1990, 90, 879.
58. Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995.
59. a) W. Heitz, Polym. Prepr. 1991, 32, 327;
60. b) V. A. Solomin, W. Heitz, Macromol. Chem. Phys. 1994, 195, 303;
61. c) U. Ziener, A. Godt, J. Org. Chem. 1997, 62, 6137.
62. M. Altmann, V. Enkelmann, F. Beer, U. H. F. Bunz, Organometallics 1996, 15, 394.
63. 3 group does not appear to have a significant influence on the optical properties (at least in the mononuclear ferrocene). Consequently, we consider the optical properties of the two trinuclear ferrocenes to be very similar.
64. R. J. Crutchley, Adv. Inorg. Chem. 1994, 41, 273.
65. C. Creutz, Prog. Inorg. Chem. 1983, 30, 1.
66. S. Barlow, D. O'Hare, Chem. Rev. 1997, 97, 637.
67. N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877.
68. Typically about 10-20 mg of ferrocenes 18, 19, 20, or 20a were allowed to react under a nitrogen atmosphere to prepare the respective mixed-valence ferrocenes.
69. The trinuclear monocations should display two different MMCT bands. The second MMCT band, however, appears to be much weaker than the first one, since the UV/Vis spectrum can be fitted using a single Gaussian band.
70. +-force field was applied.
71. a) E. E. Bunel, L. Valle, N. L. Jones, P. J. Carroll, M. Gonzalez, N. Munoz, J. M. Manriquez, Organometallics 1988, 7, 789;
72. b) Z. Yuan, G. Stringer, I. R. Jobe, D. Kreller, K. Scott, L. Koch, N. J. Taylor, T. B. Marder, J. Organomet. Chem. 1993, 452, 115.
73. C. Levanda, K. Beechgaard, D. O. Cowan, J. Org. Chem. 1976, 41, 2700.
74. A. C. Rihou, J. P. Launay, M. L. Sachtleben, H. Li, C. W. Spangler, Inorg. Chem. 1996, 35, 3735.
75. D. D. Perrin, W. L. Armarego, Purification of Laboratory Chemicals, Pergamon, Oxford, 1989.
76. T. Mangel, A. Eberhardt, U. Scherf, U. H. F. Bunz, K. Müllen, Macromol. Rapid Commun. 1995, 571.
77. R. F. Kovar, M. D. Rausch, H. Rosenberg, Organomet. Chem. Synth. 1970/71, 1, 173.