Supramolecular organization and photovoltaics of triangle-shaped discotic graphenes with swallow-tailed alkyl substituent

Advanced Materials

Volumn 20, Issue 14, 2008, Pages 2684-2689

  Feng, Xinliang ^a   Liu, Miaoyin ^a   Pisula, Wojciech ^a,b   Takase, Masayoshi ^a   Li, Jiaoli ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b EVONIK DEGUSSA GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; GRAVIMETRIC ANALYSIS; LASER INTERFEROMETRY; PHOTOVOLTAIC EFFECTS; PURIFICATION; SEMICONDUCTING ORGANIC COMPOUNDS; SUPRAMOLECULAR CHEMISTRY; THERMOGRAVIMETRIC ANALYSIS; TRIANGULATION;

ALKYL CHAINS; ALKYL SUBSTITUENTS; DECOMPOSITION TEMPERATURES; DEVICE FABRICATIONS; DISCOTIC; DISCOTICS; FACILE PURIFICATIONS; GRAPHENE; GRAPHENES; LIQUID CRYSTALLINE SEMICONDUCTORS; MONODOMAIN; ORGANIC ELECTRONICS; PHOTOVOLTAICS; SUBSTITUTION PATTERNS; SUPRAMOLECULAR ORGANIZATIONS; SYNTHESIS OF;

DIFFERENTIAL SCANNING CALORIMETRY; POLYCYCLIC AROMATIC HYDROCARBONS;

ALKYL SUBSTITUENT; DISCOTIC LIQUID CRYSTAL; DISCOTICS; GRAPHENES; PHOTOVOLTAICS; SELF ORGANIZATIONS; SELF-HEALING; SUPRAMOLECULAR ORGANIZATIONS;

EID: 54949129796     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/adma.200800642     Document Type: Article

References (39)

1. a) J. Wu, W. Pisula, K. Müllen, Chem. Rev. 2007, 107, 718.
2. b) S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hagele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni, Angew. Chem. 2007, 119, 4916;
3. Angew. Chem. Int. Ed. 2007, 46, 4837.
4. c) S. Sergeyev, W. Pisula, Y. H. Geerts, Chem. Soc. Rev. 2007, 36, 1902.
5. a) A. M. van de Craats, N. Stutzmann, O. Bunk, M. M. Nielsen, M. Watson, K. Müllen, H. D. Chanzy, H. Sirringhaus, R. H. Friend, Adv. Mater. 2003, 15, 495.
6. b) W. Pisula, A. Menon, M. Stepputat, I. Lieberwirth, U. Kolb, A. Tracz, H. Sirringhaus, T. Pakula, K. Müllen, Adv. Mater. 2005, 17, 684.
7. c) S. Xiao, J. Tang, T. Beetz, X. Guo, N. Tremblay, T. Siegrist, Y. Zhu, M. Steigerwald, C. Nuckolls, J. Am. Chem. Soc. 2006, 128, 10700.
8. a) L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R. H. Freind, J. D. MacKenzie, Science 2001, 293, 1119.
9. b) J. Li, M. Kastler, W. Pisula, J. W. F. Fobertson, D. Wasserfallen, A. C. Grimsdale, J. Wu, K. Müllen, Adv. Funct. Mater. 2007, 17, 2528.
10. F. Jäckel, M. D. Watson, K. Müllen, J. P. Rabe, Phys. Rev. Lett. 2004, 92, 188303.
11. a) A. R. Murphy, J. M. J. Frechet, Chem. Rev. 2007, 107, 1066.
12. b) S. Gunes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324.
13. a) W. Pisula, M. Kastler, D. Wasserfallen, T. Pakula, K. Müllen, J. Am. Chem. Soc. 2004, 126, 8074.
14. b) W. Pisula, M. Kastler, D. Wasserfallen, M. Mondeshki, J. Piris, I. Schnell, K. Müllen, Chem. Mater. 2006, 18, 3634.
15. a) I. Mcculloch, M. Heeney, C. Bailey, K. Genevicius, I. Macdonald, M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. Zhang, M. L. Chabinyc, R. J. Kline, M. D. Mcgehee, M. F. Toney, Nat. Mater. 2006, 5, 328.
16. b) B. S. Ong, Y. Wu, P. Liu, S. Gardner, J. Am. Chem. Soc. 2004, 126, 3378.
17. c) J. C. Maunoury, J. R. Howse, M. L. Turner, Adv. Mater. 2007, 19, 805.
18. d) K. H. Kim, Z. Chi, M. J. Cho, J. I. Jin, M. Y. Cho, S. J. Kim, J. S. Joo, D. H. Choi, Chem. Mater. 2007, 19, 4925.
19. a) M. Funahashi, F. Zhang, N. Tamaoki, Adv. Mater. 2007, 19, 353.
20. b) K. Oikawa, H. Monobe, K. Nakayama, T. Kimoto, K. Tsuchiya, B. Heinrich, D. Guillon, Y. Shiraizu, M. Yokoyama, Adv. Mater. 2007, 19, 1864.
21. c) A. J. J. M. van Breemen, P. T. Herwig, C. H. T. Chlon, J. Sweelssen, H. F. M. Schoo, S. Setayesh, W. M. Hardeman, C. A. Martin, D. M. de Leeuw, J. J. P. Valeton, C. W. M. Bastiaansen, D. J. Broer, A. R. Popa-Merticaru, S. C. J. Meskers, J. Am. Chem. Soc. 2006, 128, 2336.
22. Only the plastic crystalline phase was observed over a broad temperature range. Examples see: a) W. Pisula, Ž. Tomović, M. D. Watson, K. Müllen, J. Kussmann, C. Ochsenfeld, T. Metzroth, J. Gauss, J. Phys. Chem. B. 2007, 111, 7481.
23. b) X. Feng, W. Pisula, K. Müllen, J. Am. Chem. Soc. 2007, 129, 14116.
24. c) X. Feng, W. Pisula, L. Zhi, M. Takase, K. Müllen, Angew. Chem. 2008, 120, 1727;
25. Angew. Chem. Int. Ed. 2007, 47, 1703.
26. a) X. Yang, J. Loos, Macromolecules 2007, 40, 1353.
27. b) T. Kietzke, R. Y. C. Shin, D. A. M. Egbe, Z. K. Chen, A. Sellinger, Macromolecules 2007, 40, 4424.
28. X. Feng, J. Wu, M. Ai, W. Pisula, L. Zhi, J. P. Rabe, K. Müllen, Angew. Chem. 2007, 119, 3093:
29. Angew. Chem. Int. Ed. 2007, 46, 3033.
30. a) X. Feng, J. Wu, V. Enkelmann, K. Müllen, Org. Lett. 2006, 8, 1145.
31. b) X. Feng, W. Pisula, M. Ai, S. Gröper, J. P. Rabe, K. Müllen, Chem. Mater. 2008, 20, 1191.
32. S. Huo, Org. Lett. 2003, 5, 423.
33. 1H NMR characterizations of large PAHs are so far only available for the carbon number within 60.
34. The intensity of the α-band is too low to be detected. However, the β-band at 391 nm and the p-band as the shoulder at 440 nm are clearly resolved and show a significant bathochromic shift with respect to the hexa-perl-hexabenzocoronenes (the β-band at 360 nm).
35. a) J. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Moses, A. J. Heeger, G. C. Bazan, Nat. Mater. 2007, 6, 497. See recent reviews:
36. b) B. C. Thompson, J. M. J. Frechet, Angew. Chem. Int. Ed. 2008, 47, 58.
37. c) M. T. Lloyd, J. E. Anthony, G. G. Malliaras, Mater. Today 2007, 10, 34.
38. d) C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 2001, 11, 15.
39. W. Pisula, Ž. Tomović, C. Simpson, M. Kastler, T. Pakula, K. Müllen, Chem. Mater. 2005, 17, 4296.