Arylamine-substituted hexa-peri-hexabenzocoronenes: Facile synthesis and their potential applications as "coaxial" hole-transport materials

Angewandte Chemie - International Edition

Volumn 43, Issue 40, 2004, Pages 5331-5335

  Wu, Jishan ^a   Baumgarten, Martin ^a   Debije, Michael G ^b   Warman, John M ^b   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Arylamines; Electron transfer; Hole transport; Liquid crystals; Pi interactions

Indexed keywords

ATOMS; SYNTHESIS (CHEMICAL);

FACILE SYNTHESIS; HOLE TRANSPORT;

ORGANIC COMPOUNDS;

AROMATIC AMINE; BENZENE DERIVATIVE; HEXABENZOCORONENE; PALLADIUM; RADICAL; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ATOMIC FORCE MICROSCOPY; ELECTRIC CONDUCTIVITY; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; FILM; HYDROGENATION; LIGHT EMITTING DIODE; LIQUID CRYSTAL; MOLECULAR INTERACTION; OXIDATION; SEMICONDUCTOR; SONOGASHIRA REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 7244254381     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460174     Document Type: Article

References (33)

1. a) C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913-915;
2. b) R. H. Friend, R. W. Gymer, A. B. Holmes, J. H. Burroughes, R. N. Marks, C. Taliani, D. D. C. Bradley, D. A. Dos Santos, J. L. Brédas, M. Lögdlund, W. R. Salaneck, Nature 1999, 397, 121-128.
3. a) C. W. Tang, Appl. Phys. Lett. 1986, 48, 183-185;
4. b) U. Bach, D. Lupo, P. Compte, J. E. Moser, F. Weissörtel, J. Salbeck, H. Spreitzer, M. Grätzel, Nature 1998, 395, 583;
5. c) N. S. Sarififtci, L. Smilowitz, A. J. Heeger, F. Wudl, Science 1992, 258, 1474-1476.
6. Z. Bao, J. A. Rogers, E. Katz, J. Mater. Chem. 1999, 9, 1895-1904.
7. S. J. Zilker, ChemPhysChem 2000, 1, 72-87.
8. M. Thelakkat, Macromol. Mater. Eng. 2002, 287, 442-461.
9. a) M. D. Watson, A. Fechtenkötter, K. Müllen, Chem. Rev. 2001, 101, 1267-1300;
10. b) A. M. van de Craats, J. M. Warman, A. Fechtenkötter, J. D. Brand, M. A. Harbison, K. Müllen, Adv. Mater. 1999, 11, 1469-1472.
11. K. R. Stickley, S. C. Blackstock, J. Am. Chem. Soc. 1994, 116, 11576-11577.
12. a) C. Lambert, G. Nöll, Angew. Chem. 1998, 110, 2239-2242; Angew. Chem. Int. Ed. 1998, 37, 2107-2110;
13. a) C. Lambert, G. Nöll, Angew. Chem. 1998, 110, 2239-2242; Angew. Chem. Int. Ed. 1998, 37, 2107-2110;
14. b) C. Lambert, G. Nöll, J. Am. Chem. Soc. 1999, 121, 8434-8442;
15. c) C. Lambert, G. Nöll, Chem. Eur. J. 2002, 8, 3467-3477.
16. a) J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 1997, 62, 6066-6068;
17. b) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575-5580.
18. S. Ito, M. Wehmeier, J. D. Brand, C. Kübel, R. Epsch, J. P. Rabe, K. Müllen, Chem. Eur. J. 2000, 6, 4327-4342.
19. J. Wu, M. D. Watson, K. Müllen, Angew. Chem. 2003, 115, 5487-5491; Angew. Chem. Int. Ed. 2003, 42, 5329-5333.
20. J. Wu, M. D. Watson, K. Müllen, Angew. Chem. 2003, 115, 5487-5491; Angew. Chem. Int. Ed. 2003, 42, 5329-5333.
21. S. Taskahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630.
22. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
23. C. L. Nesloney, J. W. Kelly, J. Org. Chem. 1996, 61, 3127-3137.
24. J. A. Hyatt, Org. Prep. Proced. Int. 1991, 23, 460-463.
25. 2D WAXD was performed on a mechanically extruded fiber with the X-ray beam perpendicular to the fiber axis. For experimental details, see: I. Fischbach, T. Pakula, P. Minkin, A. Fechtenkötter, K. Müllen, H. W. Spiess, J. Phys. Chem. B 2002, 106, 6408-6418.
26. An approximate 2D monoclinic unit cell a = 2.17, b = 1.56 nm, and χ = 97° can also be determined based on the correlations of the equatorial reflections.
27. At low temperature the intramolecular charge transfer most probably was forbidden, thus only three-line ESR spectra correlated to singly charged amines were observed.
28. a) J. Bonvoisin, J. P. Launay, M. van der Auweraer, F. C. DeSchryver J. Phys. Chem. 1994, 98, 5052-5067;
29. b) V. Coropceanu, M. Malagoli, J. M. André, J. L. Brédas, J. Am. Chem. Soc. 2002, 124, 10519-10530.
30. P. G. Scheuten, J. M. Warman, M. P. de Haas, J. Phys. Chem. 1993, 97, 9863-9870.
31. a) P. M. Borsenberger, L. Pautmeier, R. Richert, H. Bässler, J. Chem. Phys. 1991, 94, 8276-8281;
32. b) P. M. Borsenberger, L. Pautmeier, H. Bässler, J. Chem. Phys. 1991, 94, 5447-5454.
33. A detailed study of the intramolecular charge transfer in the mixed-valence compounds will be presented in a separate publication.