Conjugated organomettallic ploymers containing Vollhardt's cyclobutadiene complex: Aggregation and morphologies

Chemistry - A European Journal

Volumn 7, Issue 1, 2001, Pages 117-126

  Steffen, Winfried ^a   Köhler, Bernhard ^b   Altmann, Markus ^b   Scherf, Ullrich ^b   Stitzer, Katherine ^a   Zur Loye, Hans Conrad ^a   Bunz, Uwe H F ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

^b MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Aggregation; Conjugation; Liguid crystals; Organometallic compounds; Polymers; Supramolecular chemistry

Indexed keywords

1,3 BUTADIENE; BENZENE DERIVATIVE; COBALT DERIVATIVE; CYCLOBUTADIENE; CYCLOBUTANE; ORGANOMETALLIC COMPOUND; PALLADIUM; POLYMER; POTASSIUM HYDROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; CIRCULAR DICHROISM; DIFFERENTIAL SCANNING CALORIMETRY; OPTICS; POLYMERIZATION; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

EID: 0035808376     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010105)7:1<117::aid-chem117>3.0.co;2-5     Document Type: Article

References (68)

1. M. M. Bouman, E. E. Havinga, R. A. J. Janssen, H. F. M. Shoo, H. P. J. M. Dekkers, E. W. Meijer, Mol. Cryst. Liq. Cryst. 1994, 256, 439; E. Peeters, M. P. T. Christiaans, R. A. J. Janssen, H. F. M. Shoo, H. P. J. M. Dekkers, E. W. Meijer, J. Am. Chem. Soc. 1997, 119, 9909.
2. M. M. Bouman, E. E. Havinga, R. A. J. Janssen, H. F. M. Shoo, H. P. J. M. Dekkers, E. W. Meijer, Mol. Cryst. Liq. Cryst. 1994, 256, 439; E. Peeters, M. P. T. Christiaans, R. A. J. Janssen, H. F. M. Shoo, H. P. J. M. Dekkers, E. W. Meijer, J. Am. Chem. Soc. 1997, 119, 9909.
3. For aggregation of other conjugated polymers see: a) J. K. Politis, F. B. Somoza, J. W. Kampf, M. D. Curtis, Chem. Mater. 1999, 11, 2274;
4. b) E. Conwell, Trends Polym. Sci. 1997, 5, 218;
5. c) S. A. Jenekhe, A. Osaheni, Science 1994, 265, 765;
6. d) T. Yamamoto, D. Komarudin, M. Arai, B. L. Lee, H. Sugamuna, N. Asakawa, Y. Inoue, K. Kubota, S. Sasaki, T. Fukuda, H. Matsuda, J. Am. Chem. Soc. 1998, 120, 2047.
7. a) C. E. Halkyard, M. E. Rampey, L. Kloppenburg, S. L. Studer-Martinez, U. H. F. Bunz, Macromolecules 1998, 31, 8655;
8. b) R. Fiesel, C. E. Halkyard, M. E. Rampey, L. Kloppenburg, S. L. Studer-Martinez, U. Scherf, U H. F. Bunz, Macromol. Rapid Commun. 1999, 20, 107.
9. S. D. D. V. Rughooputh, S. Hotta, A. J. Heeger, F. Wudl, J. Polym. Sci. B 1987, 25, 1071.
10. a) P. Samori, V. Francke, K. Müllen, J. R. Rabe, Chem. Eur. J. 1999, 5, 2312;
11. b) J. M. Tour, M. Kosaki, J. M. Seminario, J. Am. Chem. Soc. 1998, 120, 8486.
12. a) I. Manners, Chem. Commun. 1999, 857;
13. b) P. Nguyen, P. Gomez-Elipe, I. Manners, Chem. Rev. 1999, 99, 1515;
14. c) I. Manners, Angew. Chem. 1996, 108, 1712; Angew. Chem. Int. Ed. Engl. 1996, 35, 1603;
15. c) I. Manners, Angew. Chem. 1996, 108, 1712; Angew. Chem. Int. Ed. Engl. 1996, 35, 1603;
16. d) U. H. F. Bunz, Pure Appl. Chem. 1996, 68, 309;
17. e) D. W. Bruce, D. D'Hare, Inorganic Materials, Wiley, Chichester, 1992;
18. f) G. E. Southard, M. D. Curtis, Organometallics 1997, 16, 5618;
19. g) P. Espinet, J. L. Serrano, L. A. Oro, M. A. Esteruelas, Coord. Chem. Rev. 1992, 117, 215;
20. h) K. D. Ley, K. S. Schanze, Coord. Chem. Rev. 1998, 171, 287.
21. a) S. S. H. Mao, F. Q. Liu, T. D. Tilley, J. Am. Chem. Soc. 1998, 120, 1193;
22. b) S. S. H. Mao, T. D. Tilley, J. Organomet. Chem. 1996, 521, 425;
23. c) M. A. Buretea, T. D. Tilley, Organometallics 1997, 16, 1507;
24. d) S. S. H. Mao, T. D. Tilley, Macromolecules 1996, 29, 6362;
25. e) R. W. Heo, F. B. Somoza, T. R. Lee, J. Am. Chem. Soc. 1998, 120, 1621.
26. D. A. Foucher, B. Z. Tang, I. Manners, J. Am. Chem. Soc. 1992, 114, 6246; R. Rulkens, A. J. Lough, I. Manners, J. Am. Chem. Soc. 1994, 116, 797; R. Rulkens, Y. Ni, I. Manners, J. Am. Chem. Soc. 1994, 116, 12121; I. Manners, Chem. Commun. 1999, 857; J. A. Masay, K. N. Power, M. A. Winnik, I. Manners, Adv. Mater. 1998, 10, 1559.
27. D. A. Foucher, B. Z. Tang, I. Manners, J. Am. Chem. Soc. 1992, 114, 6246; R. Rulkens, A. J. Lough, I. Manners, J. Am. Chem. Soc. 1994, 116, 797; R. Rulkens, Y. Ni, I. Manners, J. Am. Chem. Soc. 1994, 116, 12121; I. Manners, Chem. Commun. 1999, 857; J. A. Masay, K. N. Power, M. A. Winnik, I. Manners, Adv. Mater. 1998, 10, 1559.
28. D. A. Foucher, B. Z. Tang, I. Manners, J. Am. Chem. Soc. 1992, 114, 6246; R. Rulkens, A. J. Lough, I. Manners, J. Am. Chem. Soc. 1994, 116, 797; R. Rulkens, Y. Ni, I. Manners, J. Am. Chem. Soc. 1994, 116, 12121; I. Manners, Chem. Commun. 1999, 857; J. A. Masay, K. N. Power, M. A. Winnik, I. Manners, Adv. Mater. 1998, 10, 1559.
29. D. A. Foucher, B. Z. Tang, I. Manners, J. Am. Chem. Soc. 1992, 114, 6246; R. Rulkens, A. J. Lough, I. Manners, J. Am. Chem. Soc. 1994, 116, 797; R. Rulkens, Y. Ni, I. Manners, J. Am. Chem. Soc. 1994, 116, 12121; I. Manners, Chem. Commun. 1999, 857; J. A. Masay, K. N. Power, M. A. Winnik, I. Manners, Adv. Mater. 1998, 10, 1559.
30. D. A. Foucher, B. Z. Tang, I. Manners, J. Am. Chem. Soc. 1992, 114, 6246; R. Rulkens, A. J. Lough, I. Manners, J. Am. Chem. Soc. 1994, 116, 797; R. Rulkens, Y. Ni, I. Manners, J. Am. Chem. Soc. 1994, 116, 12121; I. Manners, Chem. Commun. 1999, 857; J. A. Masay, K. N. Power, M. A. Winnik, I. Manners, Adv. Mater. 1998, 10, 1559.
31. For the formation of micelles in an organometallic block copolymer see: a) R. Resendes, J. A. Massey, H. Dorn, K. N. Power, M. A. Winnik, I. Manners, Angew. Chem. 1999, 111, 2738; Angew. Chem. Int. Ed. 1999, 38, 2570;
32. For the formation of micelles in an organometallic block copolymer see: a) R. Resendes, J. A. Massey, H. Dorn, K. N. Power, M. A. Winnik, I. Manners, Angew. Chem. 1999, 111, 2738; Angew. Chem. Int. Ed. 1999, 38, 2570;
33. b) for thermotropic organometallic polymers see: M. Altmann, U. H. F. Bunz, Angew. Chem. 1995, 107, 603; Angew. Chem. Int. Ed. Engl. 1995, 34, 569;
34. b) for thermotropic organometallic polymers see: M. Altmann, U. H. F. Bunz, Angew. Chem. 1995, 107, 603; Angew. Chem. Int. Ed. Engl. 1995, 34, 569;
35. c) M. Altmann, V. Enkelmann, G. Lieser, U. H. F. Bunz, Adv. Mater. 1995, 7, 726;
36. d) A. A. Dembek, R. R. Burch, A. E. Feiring, J. Am. Chem. Soc. 1993, 115, 2087;
37. e) I. L. Rozhanskii, I. Tomita, T. Endo, Macromolecules 1997, 30, 1222; I. Tomita, A. Nishio, T. Endo, Macromolecules 1994, 27, 7009;
38. e) I. L. Rozhanskii, I. Tomita, T. Endo, Macromolecules 1997, 30, 1222; I. Tomita, A. Nishio, T. Endo, Macromolecules 1994, 27, 7009;
39. f) N. Hagihara, K. Sonogashira, S. Takahashi, Adv. Polym. Sci. 1981, 41, 149;
40. g) S. J. Davies, B. F. G. Johnson, M. S. Kahn, J. Lewis, J. Chem. Soc. Chem. Commun. 1991, 187.
41. The term ADIMET was coined by K. Weiss: a) K. Weiss, A. Michel, E. M. Auth, U. H. F. Bunz, T. Mangel, K. Müllen, Angew. Chem. 1997, 109, 522; Angew. Chem. Int. Ed. Engl. 1997, 36, 506;
42. The term ADIMET was coined by K. Weiss: a) K. Weiss, A. Michel, E. M. Auth, U. H. F. Bunz, T. Mangel, K. Müllen, Angew. Chem. 1997, 109, 522; Angew. Chem. Int. Ed. Engl. 1997, 36, 506;
43. b) L. Kloppenburg, D. Song, U. H. F. Bunz, J. Am. Chem. Soc. 1998, 120, 7973;
44. c) U. H. F. Bunz, V. Enkelmann, L. Kloppenburg, D. Jones, K. D. Shimizu, J. B. Claridge, H. C. zur Loye, G. Lieser, Chem. Mater. 1999, 11, 1416;
45. d) L. Kloppenburg, D. Jones, J. B. Claridge, H. C. zur Loye, U. H. F. Bunz, Macromolecules 1999, 32, 4460.
46. a) U. H. F. Bunz, L. Kloppenburg, Angew. Chem. 1999, 110, 489; Angew. Chem. Int. Ed. 1999, 38, 478;
47. a) U. H. F. Bunz, L. Kloppenburg, Angew. Chem. 1999, 110, 489; Angew. Chem. Int. Ed. 1999, 38, 478;
48. b) N. Kaneta, K. Hikichi, M. Mori, Chem. Lett. 1995, 1055; A. Mortreux, M. Blanchard, J. Chem. Soc. Chem. Commun. 1974, 786.
49. b) N. Kaneta, K. Hikichi, M. Mori, Chem. Lett. 1995, 1055; A. Mortreux, M. Blanchard, J. Chem. Soc. Chem. Commun. 1974, 786.
50. a) J. R. Fritch, K. P. C. Vollhardt, Organometallics 1982, 1, 580;
51. b) see as well: G. Roidl, V. Enkelmann, R. D. Adams, U. H. F. Bunz, J. Organomet. Chem. 1999, 578, 144.
52. a) U. H. F. Bunz, Chem. Rev. 2000, 100, 1605;
53. b) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 50, 4467;
54. c) In our experience, aryl iodides couple best in the presence of piperidine as base, while aryl bromides seem to work better with diisopropylamine or Hünigs base. For an in depth discussion see ref. [13a].
55. a) L. Kloppenburg, D. Jones, U. H. F. Bunz, Macromolecules 1999, 32, 4194;
56. b) M. Rehahn, A. D. Schlüter, G. Wegner, W. J. Feast, Polymer 1989, 30, 1060;
57. c) M. Rehahn, A. D. Schlüter, G. Wegner, Makromol. Chem. 1990, 191, 1991.
58. J. M. Tour, Chem. Rev. 1996, 96, 537.
59. U. Ziener, A. Godt, J. Org. Chem. 1997, 62, 6137; H. Kukula, S. Veit, A. Godt, Eur. J. Org. Chem. 1999, 277.
60. U. Ziener, A. Godt, J. Org. Chem. 1997, 62, 6137; H. Kukula, S. Veit, A. Godt, Eur. J. Org. Chem. 1999, 277.
61. H. Hager, W. Heitz, Macromol. Chem. Phys. 1998, 199, 1821.
62. 6]. It is not clear at the moment, why a high amount of catalyst is necessary.
63. a) R. Fiesel, U. Scherf, Macromol. Rapid Commun. 1998, 19, 427;
64. b) T. Miteva, L. Palmer, L. Kloppenburg, D. Neher, U. H. F. Bunz, Macromolecules 2000, 33, 652.
65. D. Neher, Adv. Mater. 1995, 7, 691.
66. a) H. Schnablegger, M. Antonietti, C. Göltner, J. Hartmann, H. Cölfen, P. Samori, J. P. Rabe, H. Hager, W. Heitz, J. Colloid Interface. Sci. 1999, 212, 24;
67. b) A. F. Thünemann, Adv. Mater. 1999, 11, 127;
68. c) P. Samori, J. P. Rabe, K. Müllen, Adv. Mater. 2000, 12, 579.