Synthesis, structure and solvatochromism of the emission of cyano-substituted oligo(phenylenevinylene)s

European Journal of Organic Chemistry

Volumn , Issue 15, 2001, Pages 2927-2938

  Detert, Heiner ^a   Schollmeyer, Dieter ^a   Sugiono, Erli ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Fluorescence; Materials science; Oligomers; Solvatochromism; Wittig reactions

Indexed keywords

BENZENE; BENZONITRILE; CYANIDE; OLIGO(PHENYLENEVINYLENE) DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTRON; ELECTRON TRANSPORT; FLUORESCENCE; LUMINESCENCE; REACTION ANALYSIS; SOLVATION; STRUCTURE ANALYSIS;

EID: 0034884673     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200108)2001:15<2927::AID-EJOC2927>3.0.CO;2-V     Document Type: Article

References (48)

1. J. H. Burroughes, D. D. C. Bradley, A. R. Brown, R. N. Marks, K. Mackay, R. H. Friend, P. L. Burns, A. B. Holmes, Nature 1990, 347, 539-541.
2. D. Braun, A. J. Heeger, Appl. Phys. Lett. 1991, 58, 1982-1984.
3. A. Kraft, A. C. Grimsdale, A. B. Holmes, Angew. Chem. 1998, 110, 416-443;
4. Angew. Chem. Int. Ed. 1998, 37, 402-428.
5. H. F. M. Schoo, R. J. C. E. Demandt, Philips J. Res. 1998, 51, 527-533.
6. D.-H. Hwang, S. T. Kim, H. K. Shim, A. B. Holmes, S. C. Moratti, R. H. Friend, Chem. Commun. 1996, 2241-2241.
7. S.-J. Chung, J.-I. Jin, C.-H. Lee, C.-E. Lee, Adv. Mater. 1998, 10, 684-688.
8. A. Mathy, K. Ueberhofen, R. Schenk, H. Gregorius, R. Garay, K. Müllen, C. Bubeck, Phys. Rev. B. 1996, 53, 4367-4376.
9. H. Meier, H. Kretzschmann, M. Lane, W. Fraß, C. Albrecht, K. März, J. Prakt. Chem. 1994, 336, 297-302.
10. A. R. Brown, D. D. C. Bradley, P. L. Burn, J. H. Burroughes, R. H. Friend, N. C. Greenham, A. Kraft, Appl. Phys. Lett. 1994, 61, 2793.
11. N. C. Greenham, S. C. Moratti, D. D. C. Bradley, R. H. Friend, A. B. Holmes, Nature 1993, 365, 628-630.
12. Z. Peng, M. E. Calvin, Chem. Mater. 1998, 10, 1785-1788.
13. Z. Peng, J. Zhang, Synth. Met. 1999, 105, 73-78.
14. Z.-K. Chen, H. Meng, Y.-H. Lai, W. Huang, Macromol. 1999, 32, 4351-4358.
15. T. Christ, B. Glüsen, A. Greiner, A. Kettner, R. Sander, V. Stümpflen, V. Tsukruk, J. J. Wendorff, Adv. Mater. 1997, 9, 48-52
16. R. M. Gurge, M. Hickl, G. Krause, P. M. Lahti, B. Hu, Z. Yang, F. E. Karasz, Polym. Adv. Technol. 1998, 9, 504-510.
17. U. Stalmach, H. Kolshorn, I. Brehm, H. Meier, Liebigs Ann. 1996, 1449-1456.
18. K. Müllen, G. Wegner, Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, New York, 1998.
19. E. Birckner, U.-W. Grummt, H. Rost, A. Hartmann, S. Pfeiffer, H. Tillmann, H.-H. Hörhold, J. Fluoresc. 1998, 8, 73-80.
20. U. Stalmach, H. Detert, H. Meier, V. Gebhardt, D. Haarer, A. Bacher, H.-W. Schmidt, Opt. Mater. 1998, 9, 77-81.
21. J.-L. Brédas, Adv. Mater. 1995, 7, 263-274.
22. N. Dam, R. D. Scurlock, B. Wang, L. Ma, M. Sundahl, P. R. Ogilby, Chem. Mater. 1999, 11, 1302-1305.
23. U. Stalmach, H. Detert, J. Prakt. Chem. 2000, 10-16.
24. H. Tillmann, H.-H. Hörhold, presented at the 37th IUPAC Congress, Berlin, 1999, Abstract EXP-2-084, p. 694.
25. A. Lux, S. C. Moratti, W.-C. Li, A. C. Grimsdale, J. E. Davies, P. R. Raithby, J. Grüner, F. Cacialli, R.-H. Friend, A. B. Holmes, Polym. Prepr. 1996, 37, 202.
26. [25a] R. E. Gill, P. van Hutten, A. Meetsma, G. Hadziioannou, Chem. Mater. 1996, 8, 1341-1346. -
27. [25b] R. E. Gill, Proefschrift, Rijksuniversiteit Groningen, 1996.
28. H. Detert, E. Sugiono, J. Phys. Org. Chem. 2000, 13, 587-590.
29. D. Hohnholz, K.-H. Schweikart, L. R. Subamanian, M. Hanack, Adv. Mater. 1999, 8, 646-649.
30. D.-H. Hwang, M.-S. Jang, L.-M. Do, H. Y Chu, H. K. Shim. T. Zyung, Mol. Cryst. Liq. Cryst. 1999, 327, 193-196.
31. E. Lippert, Z. Elektrochem. 1957, 61, 962-975.
32. J.-L. Brédas, Adv. Mater. 1995, 7, 263-274.
33. I. D. W. Samuel, G. Rumbles, C. J. Collison, S. C. Moratti, A. B. Holmes, Chem. Phys. 1998, 227, 75-82.
34. A. Botrel, A. Le Beuze, P. Jacques, H. Straub, J. Chem. Soc., Faraday Trans. 2 1984, 80, 1235-1239.
35. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, Weinheim, 1988, pp. 286-311.
36. M. M. de Souza, G. Rumbles, I. D. W Samuel, S. C. Moratti, A. B. Holmes, Synth. Met. 1999, 101, 631-632.
37. W. Liptay, Angew. Chem. 1969, 81, 195-206.;
38. Angew. Chem. Int. Ed. Engl. 1969, 8, 177-187.
39. P. F. van Hutten, J. Wildeman, A. Meetsma, G. Hadziioannou, J. Am. Chem. Soc. 1999, 121, 5910-5918.
40. Atomic coordinates, bond lengths and angles, and thermal parameters of 4 (CCDC-149204) and 12 (CCDC-149205) can be obtained on request from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (int.) + 44-1223/336-033, E-mail: deposit@ccdc.cam.ac.uk].
41. J. R. Lackowicz, Principles of Fluorescence Spectroscopy, 2nd ed., Kluwer Academic/Plenum, New York, 1999.
42. K. Meerholz, H. Gregorius, K. Müllen, J. Heinze, Adv. Mater. 1994, 6, 671.
43. G. M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement, University of Göttingen, Germany, 1997.
44. S. Hartley, J. Chem. Soc. 1939, 1828-1836.
45. R. Brettle, D. A. Dunmur, N. J. Hindley, C. M. Marson, J. Chem. Soc., Chem. Commun. 1992, 5, 410-411.
46. A. Franke, F. F. Frickel, R. Schlecker, P. C. Thieme, Synthesis 1979, 712-714.
47. J. H. Musser, U. R. Chakraborty, S. Sciortino, R. J. Gordon, A. Khandwala, J. Med. Chem. 1987, 30, 96-104.
48. W. Stilz, H. Pommer, K. H. Koenig, BASF, DE 1112072, 1959, Chem. Abstr. 1962, 56, 2378.