From branched polyphenylenes to graphite ribbons

Macromolecules

Volumn 36, Issue 19, 2003, Pages 7082-7089

  Wu, Jishan ^a   Gherghel, Lileta ^a   Watson, Mark D ^a   Li, Jixue ^b   Wang, Zhaohui ^a   Simpson, Christopher D ^a   Kolb, Ute ^b   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CRYSTAL DEFECTS; ELECTRONIC PROPERTIES; GRAPHITE; HYDROGENATION; MOLECULAR VIBRATIONS; NANOSTRUCTURED MATERIALS; OXIDATION; RAMAN SPECTROSCOPY; SOLUBILITY; SYNTHESIS (CHEMICAL); TRANSMISSION ELECTRON MICROSCOPY;

GRAPHITE RIBBONS; GRAPHITIC NANORIBBONS; INTRAMOLECULAR OXIDATIVE CYCLODEHYDROGENATION; POLYPHENYLENES;

POLYOLEFINS;

EID: 0141509098     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0257752     Document Type: Article

References (62)

1. (a) Scherf, U. J. Mater. Chem. 1999, 9, 1853-1864.
2. (b) Scherf, U.; Müllen, K. Makromol. Chem. Rapid Commun. 1991, 12, 489.
3. (c) Freund, T.; Scherf, U.; Müllen, K. Macromolecules, 1995, 28, 547.
4. (d) Schlüter, A.; Löffler, M.; Enkelmann, V. Nature (London) 1994, 368, 831-834.
5. (e) Sclicke, B.; Schirmer, H.; Schlüter, A. Adv. Mater. 1995, 7, 544-546.
6. (f) Löffler, M.; Schlüter, A.; Gessler, K.; Saenger, W.; Toussaint, J.; Bredas, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2209-2212.
7. Löffler, M.; Schlüter, A.; Gessler, K.; Saenger, W.; Toussaint, J.; Bredas, J. Angew. Chem. 1994, 106, 2218.
8. (g) Chmil, K.; Scherf, U. Acta Polym. 1997, 48, 208.
9. (h) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc. 1994, 116, 7895.
10. (i) Tour, J. M.; Lamba, J. S. S. J. Am. Chem. Soc. 1993, 115, 4935.
11. (j) Tour, J. M.; Lamba, J. S. S. J. Am. Chem. Soc. 1994, 116, 11723.
12. (k) Tsuda, A.; Osuka, A. Science 2001, 293, 79-82.
13. (l) Tsuda, A.; Osuka, A. Adv. Mater. 2002, 14, 75-79.
14. (a) Watson, M.; Fechtenbötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267-1300.
15. (b) Samori, P.; Fechtenkötter, A.; Jäckel, F.; Böhme, T.; Müllen, K.; Rabe, J. P. J. Am. Chem. Soc. 2001, 123, 11462-11467.
16. (c) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. Science 2001, 293, 1119-1122.
17. (d) Müller, M.; Kübel, C.; Müllen, K. Chem.-Eur. J. 1998, 4, 2099-2109.
18. (e) Iyer, V. S.; Yoshimura, K.; Enkelmann, V.; Epsch, R.; Rabe, J.; Müllen, K. Angew. Chem., Int. Ed. 1998, 37, 2696-2699.
19. Iyer, V. S.; Yoshimura, K.; Enkelmann, V.; Epsch, R.; Rabe, J.; Müllen, K. Angew. Chem. 1998, 110, 2843-2846.
20. (f) Dötz, F.; Brand, J. D.; Ito, S.; Gherghel, L.; Müllen, K. J. Am. Chem. Soc. 2000, 122, 7707-7717.
21. (g) Fechtenbötter, A.; Tchebotareva, N.; Watson, M.; Müllen, K. Tetrahedron Symp. 2001, 57, 3769-3783.
22. (h) Herwig, P.; Kayser, C.; Müllen, K.; Spiess, H. W. Adv. Mater. 1996, 8, 510-513.
23. (i) van de Craats, A. M.; Warman, J. M.; Fechenbötter, A.; Brand, J. D.; Harbison, M. A.; Müllen, K. Adv. Mater. 1999, 11, 1469-1472.
24. (j) Fechtenbötter, A.; Saalwächter, K.; Harbison, M. A.; Müllen, K.; Spiess, J. W. Angew. Chem., Int. Ed. Engl. 1999, 38, 3039-3042.
25. Fechtenbötter, A.; Saalwächter, K.; Harbison, M. A.; Müllen, K.; Spiess, J. W. Angew. Chem. 1999, 111, 3224-3228.
26. (k) Stabel, A.; Herwig, P.; Mullen, K. Angew. Chem. 1995, 107, 335-339.
27. Stabel, A.; Herwig, P.; Mullen, K. J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1609-1611.
28. (l) Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen, K. Angew. Chem., Int. Ed. 1997, 36, 1604-1607.
29. Iyer, V. S.; Wehmeier, M.; Brand, J. D.; Keegstra, M. A.; Müllen K. Angew. Chem. 1997, 109, 1676-1679.
30. (m) Müller, M.; Iyer, V. S.; Kübel, C.; Enkelmann, V.; Müllen, K. Angew. Chem. 1997, 109, 1679-1682.
31. (n) Simpson, C. D.; Brand, J. D.; Berresheim, A. J.; Przybilla, L.; Räder, H. J.; Müllen, K. Chem.-Eur. J. 2002, 8, 1424-1429.
32. (o) Clar, E. Polycyclic Hydrocarbons; Springer: Berlin, Göttingen, and Heidelberg Germany; Academic Press Inc.: London, 1964; Vols. I and II.
33. (p) Clar, E. The Aromatic Sextet; Wiley: London, 1972.
34. (q) Armitt, J. W.; Robinson, R. J. Chem. Soc. 1925, 1604.
35. (r) Gherghel, L.; Müllen, K. Manuscript in preparation.
36. Marting, R. E.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1999, 38, 1350-1377
37. Marting, R. E.; Diederich, F. Angew. Chem. 1999, 111, 1440-1469.
38. (a) Shifrina, Z. B.; Averina, M. S.; Rusanov, A. L.; Wagner, M.; Müllen, K. Macromolecules 2000, 33, 3525-3529.
39. (b) Mukamal, H.; Harris, F. W.; Rakutis, R. O.; Stille, J. K. Polym. Prepr. (Am. Chem. Soc. Div. Polym. Chem.) 1967, 8, 496.
40. (c) Stille, J. K.; Harris, F. W.; Rakutis, R. O.; Mukamal H. J. Polym. Sci., Part B 1966, 4, 791.
41. (d) Stille, J. K.; Rakutis, R. O.; Mukamul, H.; Harris, F. W. Macromolecules 1968, 1, 431.
42. (e) Stille, J. K.; Noren, G. K. J. Polym. Sci., Part B 1969, 7, 525.
43. (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
44. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
45. Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578-4593.
46. Taskahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
47. Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem., Int. Ed. 1994, 33, 1306
48. Schumm, J. S.; Pearson, D. L.; Tour, J. M. Angew. Chem. 1994, 106, 1445.
49. 78 graphite segment (as shown in Chart 1). Simpson, C. D.; Müllen, K.; et al. Manuscript in preparation.
50. Jones, R. N, Sandorfy, C. Chemical Applications of Spectroscopy; In Techniques of organic chemistry; Weissberger, A., Ed.; Interscience: New York, 1956, Vol. IX.
51. (a) Castiglioni, C.; Mapelli, C.; Negri, F.; Zerbi, G. J. Chem. Phys. 2001, 114, 963-974.
52. (b) Castiglioni, C.; Negri, F.; Rigolio, M.; Zerbi, G. J. Chem. Phys. 2001, 115, 3769-3778.
53. (c) Negri, F.; Castiglioni, C.; Tommasini, M.; Zerbi, G. J. Phys. Chem. A 2002, 106, 3306-3317.
54. (d) Mapelli, C.; Castiglioni, C.; Zerbi, G.; Müllen, K. Phys. Rev. B 1999, 60, 12710-12725.
55. (e) Mapelli, C.; Castiglioni, C.; Meroni, E.; Zerbi, G. J. Mol. Struct. 1999, 481, 615-620.
56. (f) Rigolio, M.; Castiglioni, C. Zerbi, G.; Negri, F. J. Mol. Struct. 2001, 563-564, 79-87.
57. Ferrari, A. C.; Robertson, J. Phys. Rev. B 2000, 61, 1.
58. Yamamoto, T.; Morita, A.; Miyazaki, Y.; Maruyama, T.; Wakayama, H.; Zhou, Z.-H.; Nakamura, Y.; Kanbara, T.; Sasaki, S.; Kubota, K. Macromolecules 1992, 25, 1214.
59. Weiss, K.; Beernink, G.; Dötz, F.; Birkner, A.; Müllen, K.; Wöll, C. H. Angew. Chem., Int. Ed. Engl. 1999, 38, 3748.
60. Sautter, A.; Thalacker, C.; Würthner, F. Angew. Chem., Int. Ed. 2001, 40, 4425-28.
61. Li, L.-S.; Walda, J.; Manna, L.; Alivisatos, A. P. Nano Lett. 2002, 2, 557-560.
62. Przybilla, L.; Brand, J. D.; Yoshimura, K.; Räder, J.; Müllen, K. Anal. Chem. 2000, 72, 4591.