Synthesis, characterization, and electron-transport property of perfluorinated phenylene dendrimers [16]

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1832-1833

  Sakamoto, Youichi ^a   Suzuki, Toshiyasu ^a   Miura, Atsushi ^b   Fujikawa, Hisayoshi ^b   Tokito, Shizuo ^b   Taga, Yasunori ^b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b Rd Management Section   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; DENDRIMER; OLIGOMER; PERFLUORO COMPOUND; PHENYL GROUP;

BROMINATION; DIFFERENTIAL SCANNING CALORIMETRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; LETTER; LIGHT EMITTING DIODE; MASS SPECTROMETRY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TEMPERATURE; THERMOSTABILITY;

EID: 0034049214     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja994083z     Document Type: Letter

References (29)

1. Electronic Materials: The Oligomer Approach; Müllen, K., Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998.
2. For recent reviews, see: (a) Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121-128. (b) Sheats, J. R.; Antoniadis, H.; Hueschen, M.; Leonard, W.; Miller, J.; Moon, R.; Roitman, D.; Stocking A. Science 1996, 273, 884-888.
3. For recent reviews, see: (a) Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121- 128. (b) Sheats, J. R.; Antoniadis, H.; Hueschen, M.; Leonard, W.; Miller, J.; Moon, R.; Roitman, D.; Stocking A. Science 1996, 273, 884-888.
4. (a) Dendrimers; Vögtle, F., Ed.; Topics in Current Chemistry No. 197; Springer-Verlag: Berlin, 1998.
5. (b) Carbon Rich Compounds I; Meijere, A. de, Ed.: Topics in Current Chemistry No. 196; Springer-Verlag: Berlin, 1998.
6. (a) Strukelj, M.; Papadimitrakopoulos, F.; Miller, T. M.; Rothberg, L, J. Science 1995, 267, 1969-1972.
7. (b) Tamao, K.; Uchida, M.; Izumizawa, T.; Furukawa, K.; Yamaguchi, S. J. Am. Chem. Soc. 1996, 118, 11974-11975.
8. (c) Noda, T.; Shirota, Y. J. Am. Chem. Soc. 1998, 120, 9714-9715 and references therein.
9. Miller et al. reported partially fluorinated phenylene dendrimers. Miller T. M.; Neenan, T. X.; Zayas, R.; Bair, H. E. J. Am. Chem. Soc. 1992, 114, 1018-1025.
10. (a) Chemistry of Organic Fluorine Compounds II: A Critical Review; Hudlický, M., Pavlath, A. E., Eds.; ACS Monograph 187; American Chemical Society: Washington, DC, 1995.
11. (b) Organofluorine Chemistry: Principle and Commercial Applications; Banks, R. E., Smart, B. E., Tatlow, J. C., Eds.; Topics in Applied Chemistry; Plenum Press: New York, 1994.
12. For example, perfluoro-3,3′,5,5′-tetrakis(phenyl)-1,1′-biphenyl: Kobrina, L. S.; Salenko, V. L.; Yakobson, G. G. J. Fluorine Chem. 1976, 8, 193-207.
13. Cairncross, A.; Sheppard, W. A.; Wonchoba, E. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. VI, pp 875-882.
14. Cairncross, A.; Sheppard, W. A.; Wonchoba, E. Organic Syntheses; Wiley & Sons: New York, 1988; Collect. Vol. VI, pp 875-882.
15. Pozdnyakovich, Yu. V.; Shteingarts, V. D. Zh. Org. Khim. 1977, 13, 1911-1917.
16. 3 and 6 in the presence of Pd(0) or Pd(II) catalysts gave 1 in 5%. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley & Sons: New York, 1998. (b) Deacon, G. B.; Gatehouse B. M.; Nelson-Reed, K. T. J. Organomet. Chem. 1989, 359, 267-283.
17. 3 and 6 in the presence of Pd(0) or Pd(II) catalysts gave 1 in 5%. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley & Sons: New York, 1998. (b) Deacon, G. B.; Gatehouse B. M.; Nelson-Reed, K. T. J. Organomet. Chem. 1989, 359, 267-283.
18. See Supporting Information for the experimental details.
19. The reaction of perfluoro-3,5-bis(phenyl)phenylcopper and 6 gave a complex mixture.
20. Wagner, H. J.; Loutfy, R. O.; Hsiao, C.-K. J. Mater. Sci. 1982, 17, 2781-2791.
21. Tanaka, H.; Tokito, S.; Taga, Y.; Okada, A. J. Chem. Soc., Chem. Commun. 1996, 2175-2176.
22. (a) Hung, L. S.; Tang, C. W.; Mason, M. G. Appl. Phys. Lett. 1997, 70, 152-154.
23. (b) Mori, T.; Fujikawa, H.; Tokito, S.; Taga, Y. Appl. Phys. Lett. 1998, 73, 2763-2765.
24. After a few days, a decrease of luminance was observed for the device with 3 because of crystallization.
25. 3 is -2.36 V under the same conditions.
26. 3. Curioni, A.; Andreoni, W. J. Am. Chem. Soc. 1999, 121, 8216-8220 and references therein.
27. (a) Tokuhisa, H.; Era, M.; Tsutsui, T.; Saito, S. Appl. Phys. Lett. 1995, 66, 3433-3435.
28. (b) Redecker, M.; Bradley, D. D. C.; Jandke, M.; Strohriegl, P. Appl. Phys. Lett. 1999, 75, 109-111.
29. 2 at 13.7 V. Further experiments are being carried out and will be reported elsewhere. Heidenhain, S.; Sakamoto, Y.; Miura, A.; Fujikawa, H. Unpublished work, 1999.