Synthesis and spectroscopic properties of finite Ph 2N-containing oligo(arylenevinylene) derivatives that emit blue to red fluorescence

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1131-1134

  Li, Chien Le ^a   Shieh, Shwu Ju ^b   Lin, Shien Chang ^b   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b Development Center   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

NITRILE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONJUGATION; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0141742107     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034246v     Document Type: Article

References (33)

1. (a) Oelkrug, D.; Tompert, A.; Gierschner, J.; Egelhaaf, H.-J.; Hanack, M.; Hohloch, M.; Steinhuber, E. J. Phy. Chem. B 1998, 102, 1902-1907.
2. (b) Electronic Materials: The Oligomer Approach; Mullen, K., Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
3. (c) Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
4. (d) Bunz, U. F. W. Chem. Rev. 2000, 100, 1605.
5. (a) Tang, C. W.; Van Slyke, S. A. Appl. Phys. Lett. 1987, 51, 913-915.
6. (b) Tang, C. W.; Van Slyke, S. A.; Chen, C. H. J. Appl. Phys. 1989, 65, 3610-3616.
7. (c) Service, R. F. Science 1996, 273, 878-880.
8. (d) Sheats, J. R.; Antoniadis, H.; Mueschen, M.; Leonard, W.; Miller, J. ; Moon, R.; Roitman, D.; Stocking, A. Science 1996, 273, 884-888.
9. (a) Irie, M. Chem. Rev. 2000, 100, 1685.
10. (b) Repinec, S. T.; Sension, R. J.; Szarka, A. Z.; Hochstrasser, R. M. J. Phys. Chem. 1991, 95, 10380
11. (a) Bosshard, C.; Sutter, K.; Pretre, P.; Hulliger, J.; Florsheimer, M.; Kaatz, P.; Gunter, P. Organic Nonlinear Optical Materials; Gordon and Breach Science Publishers: Amsterdam, The Netherlands, 1995; Vol. 1.
12. (b) Nalwa, H. S.; Myata, S. Nonlinear Optics of Organic Molecules and Polymers; CRC Press: Boca Raton, FL, 1997
13. (a) Wienk, M. M.; Janssen, R. A. J. J. Am. Chem. Soc. 1996, 118, 10625.
14. (b) Wienk, M. M.; Janssen, R. A. J. J. Am. Chem. Soc. 1997, 119, 4492.
15. (a) Maddux, T.; Li, W.; Yu, L. J. Am. Chem. Soc. 1997, 119, 844-845.
16. (b) Shrishendu, K. D.; Maddux, T.; Yu, L. J. Am. Chem. Soc. 1997, 119, 9079-9080.
17. (a) Ohmori, Y.; Tada, N.; Fujii, A. Thin Solid Films 1998, 331 (1-2), 89-95.
18. (b) Fukuda, Y.; Watanabe, T.; Wakimoto, T. Synth. Met. 2000, 111, 1-6.
19. (a) Yang, J.-S.; Chiuo, S.-Y.; Liau, K.-L. J. Am. Chem. Soc. 2002, 124, 2518-2528.
20. (b) Lewis, F. D.; Kalgutkar, R. S.; Yang, J.-S. J. Am. Chem. Soc. 1999, 121, 12045-12053.
21. (c) Lewis, F. D.; Yang, J.-S. J. Am. Chem. Soc. 1997, 119, 3834-3835.
22. (d) Lewis, F. D.; Weigel, W. J. Phys. Chem. A 2000, 104, 8146-8153.
23. (a) Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863-1874.
24. (b) Albota, M.; Beljonne, D.; Bredas, J. L.; Ehrlich, J. E.; Fu, J. Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCordMaughon, D.; Perry, J. W.; Rockel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X. L.; Xu, C. Science 1998, 281, 1653-1656.
25. (a) In a model reaction, the 1,1-regioisomer in the Heck reaction was separated in less than 4% yield: Peng, Z. H.; Yu, L. Manuscript in preparation.
26. Also see: (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558.
27. (c) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. Synlett 1992, 871.
28. (a) Manfred, T. R.; Gunther, L.; Renate, S. Angew Chem., Int. Ed. 1998, 37, 481-483.
29. (b) Rajender, S. V.; Kannan, P. N.; Per, J. L. Tetrahedron Lett. 1999, 40, 2075-2078.
30. Gu, Y.; Pritzkow, H.; Siebert, W. Eur. J. Inorg. Chem. 2001, 373-380.
31. Brannon, J. H.; Magde, D. Absolute quantum yield determination by thermal blooming. Fluorescein, J. Phys. Chem. 1978, 82, 705-709.
32. Calculation of dihedral angles between two phenyl planes is performed on the ground-state structure using MOPAC-AM1 computations.
33. o′= + 0.55 V vs Ag/AgCl (satd).