Folding a conjugated chain: Oligo(o-phenyleneethynylene-alt-p- phenyleneethynylene)

Organic Letters

Volumn 10, Issue 19, 2008, Pages 4283-4286

  Zhu, Ningbo ^a   Hu, Wei ^a   Han, Shuliang ^a   Wang, Qi ^a   Zhao, Dahui ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZENE DERIVATIVE; OILGO(2 PHENYLENEETHYNYLENE ALT 4 PHENYLENEETHYNYLENE); OILGO(2-PHENYLENEETHYNYLENE-ALT-4-PHENYLENEETHYNYLENE); POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ULTRAVIOLET SPECTROPHOTOMETRY;

ALKYNES; BENZENE DERIVATIVES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYMERS; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 55449107766     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801677s     Document Type: Article

References (38)

1. Kiebooms, R.; Lee, K.; Menon, R. Synthesis, Electrical, and Optical Properties of Conjugated Polymers. In Handbook of Advanced Electronic and Photonic Materials and Devices; Nalwa, H. S., Ed.; Academic Press: 2000; Vol. 8, pp 1-102.
2. Reese, C.; Roberts, M.; Ling, M.; Bao, Z. Mater. Today 2004, 7 (9), 20.
3. (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.; Bredas, J. L.; Logdlund, M.; Salaneck, W. R. Nature 1999, 397, 121.
4. (b) Braun, D. Mater. Today 2002, 5 (6), 32.
5. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007, 107, 1324.
6. (a) Thomas, S. W., III; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339.
7. (b) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
8. Samuel, I. D. W.; Turnbull, G. A. Mater. Today 2004, 7 (9), 28.
9. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491.
10. Han, J. J.; Shaller, A. D.; Wang, W.; Li, A. D. Q. J. Am. Chem. Soc. 2008, 130, 6974.
11. Bradford, V. J.; Iverson, B. L. J. Am. Chem. Soc. 2008, 130, 1517.
12. (a) Foldamers: Structure, Properties and Applications; Hecht, S., Hue, I., Eds.; Wiley-VCH: Weinheim, 2007.
13. (b) Smaldone, R. A.; Moore, J. S. Chem.-Eur. J. 2008, 14, 2650.
14. (c) Cheng, P. Curr. Opin. Struct. Biol. 2004, 14, 512.
15. (d) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
16. (e) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219, and references therein.
17. For most recent studies on foldamers and their functions, see: (a) Cai, W.; Wang, G.-T.; Xu, Y.-X.; Jiang, X.-K.; Li, Z.-T. J. Am. Chem. Soc. 2008, 130, 6936.
18. (b) Meudtner, R. M.; Hecht, S. Angew. Chem., Int. Ed. 2008, 47, 4926.
19. (c) Bao, C.; Kauffmann, B.; Gan, Q.; Srinivas, K.; Jiang, H.; Hue, I. Angew. Chem., Int. Ed. 2008, 47, 4153.
20. (d) Home, W. S.; Boersma, M. D.; Windsor, M. A.; Gellman, S. H. Angew. Chem., Int. Ed. 2008, 47, 2853, and ref 9.
21. (a) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793.
22. (b) Stone, M. T.; Heemstra, J. M.; Moore, J. S. Acc. Chem. Res. 2006, 39, 11.
23. (c) Smaldone, R. A.; Moore, J. S. J. Am. Chem. Soc. 2007, 129, 5444.
24. (d) Tan, C.; Pinto, M. R.; Schanze, K. S. Adv. Mater. 2004, 16, 1208.
25. (e) Ishitsuka, Y.; Arm, L.; Majewski, J.; Frey, S.; Ratajczek, M.; Kjaer, K.; Tew, G. N.; Lee, K. Y. C. J. Am. Chem. Soc. 2006, 128, 13123.
26. (a) Grubbs, R. H.; Kratz, D. Chem. Ber. Reel. 1993, 126, 149.
27. (b) Shotwell, S.; Windschief, P. M.; Smith, M. D.; Bunz, U. H. F. Org. Lett. 2004, 6, 4151.
28. (c) Khan, A.; Hecht, S. J. Polym. Sci., Pan A 2006, 44, 1619.
29. (a) Jones, T. V.; Blatchly, R. A.; Tew, G. N. Org. Lett. 2003, 5, 3297.
30. (b) Jones, T. V.; Slutsky, M. M.; Laos, R.; de Greef, T. F. A.; Tew, G. N. J. Am. Chem. Soc. 2005, 127, 17235.
31. (c) Slutsky, M. M.; Jones, T. V.; Tew, G. N. J. Org. Chem. 2007, 72, 342.
32. (d) Jones, T. V.; Slutsky, M. M.; Tew, G. N. New J. Chem. 2008, 32, 676.
33. Anand, S.; Varnavski, O.; Marsden, J. A.; Haley, M. M.; Schlegel, H. B.; Goodson, T., III. J. Phys. Chem. A. 2006, 110, 1305.
34. For examples of previously reported molecules containing the p-PE-o-PE unit, see: (a) Ohkita, M.; Ando, K.; Suzuki, T.; Tsuji, T. J. Org. Chem. 2000, 65, 4385.
35. (b) Anderson, S. Chem.-Eur. J. 2001, 7, 4706.
36. (c) Nierengarten, J.-F.; Zhang, S.; Gegout, A.; Urbani, M.; Armaroli, N.; Marconi, G.; Rio, Y. J. Org. Chem. 2005, 70, 7550.
37. (d) Shirai, Y.; Osgood, A. J.; Zhao, Y.; Yao, Y.; Saudan, L.; Yang, H.; Yu-Hung, C.; Alemany, L. B.; Sasaki, T.; Morin, J.-F.; Guerrero, J. M.; Kelly, K. F.; Tour, J. M. J. Am. Chem. Soc. 2006, 128, 4854.
38. The emission quantum yield of 1 in cyclohexane did not decrease with increasing concentration, which also suggested that no significant intermolecular aggregation occurred.