Synthesis and characterization of novel para- and meta-phenylenevinylene derivatives: Fine tuning of the electronic and optical properties of conjugated materials

Journal of Physical Chemistry B

Volumn 106, Issue 25, 2002, Pages 6442-6450

  Pascal, L ^a   Vanden Eynde, J J ^a   Van Haverbeke, Y ^a   Dubois, P ^b   Michel, A ^b   Rant, U ^c   Zojer, E ^c   Leising, G ^d   Van Dorn, L O ^e   Gruhn, N E ^e   Cornil, J ^b,e   Bredas J L ^b,e  

^a Universiteó de Mons Hainaut   (Belgium)

^b UNIVERSITY OF MONS   (Belgium)

^c GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^d AT&S Austria Technologie & Systemtechnik Aktiengesellschaft   (Austria)

^e UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ULTRAVIOLET PHOTOELECTRON SPECTROSCOPY;

ELECTRONIC PROPERTIES; LIGHT ABSORPTION; LIGHT EMISSION; MOLECULAR STRUCTURE; PHOTOELECTRON SPECTROSCOPY; SYNTHESIS (CHEMICAL);

ORGANIC POLYMERS;

EID: 0037183058     PISSN: 10895647     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp025748d     Document Type: Article

References (55)

1. Sheats, J.R.; Antoniadis, H.; Hueschen, M.; Leonard, W.; Miller, J.; Moon, R.; Roitman, D.; Stocking, A. Science 1996, 273, 884.
2. 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.
3. Tang, C.W.; van Slyke, S.A. Appl. Phys. Lett. 1987, 51, 913.
4. Pardo, D.A.; Jabbour, G.E.; Peyghambarian, N. Adv. Mater. 2000, 12, 1249.
5. Greenham, N.C.; Moratti, S.C.; Bradley, D.D.C.; Friend, R.H.; Holmes, A.B. Nature 1993, 365, 268.
6. Chung, S.J.; Kwon, K.Y.; Lee, S.W.; Jin, J.I.; Lee, C.H.; Lee, C.E.; Park, Y. Adv. Mater. 1998, 10, 1112.
7. Zheng, M.; Ding, L.M.; Gurel, E.E.; Lahti, P.M., Karasz, F.E. Macromolecules 2001, 34, 4124.
8. Lee, Y.; Chen, X.; Chen, S.A.; Wei, P.K.; Fann, W.S. J. Am. Chem. Soc. 2001, 123, 2296.
9. Cao, Y.; Parker, I.D.; Yu, G.; Zhang, C.; Heeger, A.J. Nature 1999, 397, 414.
10. Ohmori, Y.; Hironaka, Y.; Yoshida, R.; Fujii, A.; Tada, N.; Yoshino, K. Polym. Adv. Technol. 1997, 8, 403.
11. Sariciftci, N.S.; Smilowitz, L.; Heeger, A.J.; Wudl, F. Science 1992, 258, 1474.
12. Halls, J.J.M.; Walsh, C.A.; Greenham, N.C.; Marseglia, E.A.; Friend, R.H.; Moratti, S.C.; Holmes, A.B. Nature 1995, 376, 498.
13. Smolenyak, P.; Peterson, R.; Nebesny, K.; Törker, M.; O'Brien, D.F.; Armstrong, N.R. J. Am. Chem. Soc. 1999, 121, 8628.
14. Yu, G.; Wang, J.; McElvain, J.; Heeger, A.J. Adv. Mater. 1998, 17, 1431.
15. Halls, J.J.M.; Cornil, J.; dos Santos, D.A.; Silbey, R.; Wang, D. H.; Holmes, A.B.; Brédas, J.L.; Friend, R.H. Phys. Rev. B 1999, 60, 5721.
16. Baldo, M.A.; O'Brien, D.F.; You, Y.; Shoustikov, A.; Silbey, S.; Thompson, M.E.; Forrest, S.R. Nature 1998, 395, 151.
17. Cleave, V.; Yahioglu, G.; Le Barny, P.; Friend, R.H.; Tessler, N. Adv. Mater. 1999, 11, 285.
18. Vanden Eynde, J.J.; Pascal, L.; Dubois P.; Van Haverbeke Y. Synth. Commun. 2001, 31, 3167.
19. Kraft, A.; Grimsdale, A.C.; Holmes, A.B. Angew. Chem., Int. Ed. 1998, 37, 403.
20. Primary Photoexcitations in Conjugated Polymers: Molecular Exciton versus Semiconductor Band Model; Saficiftci, N.S., Ed.; World Scientific: Singapore, 1997.
21. Lhost, O.; Brédas, J.L. J. Chem. Phys. 1992, 96, 5279.
22. Karabunarliev, S.; Baumgarten, M.; Tyutyulkov, N.; Müllen, K. J. Phys. Chem. 1994, 98, 11892.
23. Wienk, M.M.; Janssen, R.A.J. J. Am. Chem. Soc. 1997, 119, 4492.
24. Cornil, J.; Gruhn, N.E.; dos Santos, D.A.; Malagoli, M.; Lee, P.A.; Barlow, S.; Thayumanavan, S.; Marder, S.R.; Armstrong, N.R.; Brédas, J.L. J. Phys. Chem. A 2001, 105, 5206.
25. Cornil, J.; Beljonne, D.; dos Santos, D.A.; Brédas, J.L. Synth. Met. 1996, 76, 101.
26. Cornil, J.; dos Santos, D.A.; Beljonne, D.; Brédas, J.L. J. Phys. Chem. 1995, 99, 5604.
27. Horowitz, G. Adv. Mater. 1998, 10, 365.
28. Katz, H.E.; Lovinger, A.J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.Y.; Dodabalapur, A. Nature 2000, 404, 478.
29. Peeters, E.; Ramos, A.M.; Meskers, S.C.J.; Janssen, R.A.J. J. Chem. Phys. 2000, 112, 9445.
30. Cornil, J.; Beljonne, D.; Heller, C.M.; Campbell, I.H.; Laurich, B.K.; Smith, D.L.; Bradley, D.D.C.; Müllen, K.; Brédas, J.L. Chem. Phys. Lett. 1997, 278, 139.
31. Burroughes, J.H.; Bradley, D.D.C.; Brown, A.R.; Marks, R.N.; Friend, R.H.; Burn, P.L.; Holmes, A.B. Nature 1990, 347, 359.
32. Lane, P.A.; Cadby, A.J.; Mellor, H.; Martin, S.J.; Lidzey, D.G.; Bradley, D.D.C.; Lipson, S.M.; O'Brien, D.F.; Blau, W. Phys. Rev. B 2000, 62, 15718.
33. Liao, L.; Pang, Y.; Ding, L.; Karasz, F.E. Macromolecules 2001, 34, 7300.
34. Pascal, L.; Vanden Eynde, J.J.; Van Haverbeke, Y.; Dubois, P.; Cornil, J.; Brédas, J.L. Manuscript in preparation.
35. Egelhaaf, H.J.; Gierschner, J.; Oelkrug, D. Synth. Met. 1996, 83, 221.
36. Wang, H.; Helgeson, R.; Ma, B.; Wudl, F. J. Org. Chem. 2000, 65, 5862.
37. Müllner, R.; Winkler, B.; Stelzer, F.; Tasch, S.; Hochfilzer, C.; Leising, G. Synth. Met. 1999, 105, 129.
38. Gierschner, J.; Lüer, L.; Oelkrug, D.; Musluoglu, E.; Behnisch, B.; Hanack, M. Adv. Mater. 2000, 12, 757.
39. Beljonne, D.; Shuai, Z.; Pourtois, G.; Brédas, J.L. J. Phys. Chem. A 2001, 105, 3899.
40. Hertel, D.; Setayesh, S.; Nothofer, H.G.; Scherf, U.; Müllen, K.; Bässler, H. Adv. Mater. 2001, 13, 65.
41. Ephardt, H.; Fromherz, P. J. Phys. Chem. 1989, 93, 7717.
42. Gabriel, S.; Colman, J. Chem. Ber. 1903, 36, 3379.
43. Haroutounian, S.; Katzenellenbogen, J. Tetrahedron 1995, 51, 1585.
44. Hasegawa, M.; Endo, Y.; Aoyama, M.; Saigo, K. Bull. Chem. Soc. Jpn. 1989, 62, 1556.
45. Strul, M.; Zugravescu, I. Rev. Roum. Chim. 1971, 16, 1877.
46. Reynolds, G.A.; Drexhage, K.H. Opt. Commun. 1975, 13, 222.
47. Westcott, B.L.; Gruhn, N.E.; Enemark, J.H. J. Am. Chem. Soc. 1998, 120, 3382 and references therein.
48. Lichtenberger, D.L.; Copenhaver, A.S. J. Electron Spectrosc. Relat. Phenom. 1990, 50, 335.
49. Reynolds, G.A.; Drexhage, K.H. Opt. Commun. 1975, 13, 222.
50. Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902.
51. Zerner, M.C.; Loew, G.H.; Kichner, R.F.; Mueller-Westerhoff, U.T. J. Am. Chem. Soc. 1980, 102, 589.
52. Cornil, J.; Vanderdonckt, S.; Lazzaroni, R.; dos Santos, D.A.; Thys, G.; Geise, H.J.; Yu, L.M.; Szablewski, M.; Bloor, D.; Lögdlund, M.; Salaneck, W.R.; Gruhn, N.E.; Lichtenberger, D.L.; Lee, P.A.; Armstrong, N.R.; Brédas, J.L. Chem. Mater. 1999, 11, 2436.
53. Hill, I.G.; Kahn, A.; Cornil, J.; dos Santos, D.A.; Brédas, J.L. Chem. Phys. Lett. 2000, 317, 444.
54. Cornil, J.; dos Santos, D.A.; Crispin, X.A.; Silbey, R.; Brédas, J. L. J. Am. Chem. Soc. 1998, 120, 1289.
55. Brédas, J.L.; Cornil, J.; Beljonne, D.; dos Santos, D.A.; Shuai, Z. Acc. Chem. Res. 1999, 32, 267.