Dialkynylpyrenes: Strongly fluorescent, environment-sensitive DNA building blocks

Journal of the American Chemical Society

Volumn 130, Issue 46, 2008, Pages 15285-15287

  Bittermann, Holger ^a   Siegemund, Doreen ^a   Malinovskii, Vladimir L ^a   Häner, Robert ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DNA HYBRID; OLIGONUCLEOTIDE; PYRENE DERIVATIVE;

ABSORPTION; ARTICLE; CHEMICAL STRUCTURE; DNA SYNTHESIS; FLUORESCENCE; HYDROGEN BOND; ULTRAVIOLET SPECTROSCOPY;

ALKYNES; AMIDES; CIRCULAR DICHROISM; DNA; FLUORESCENT DYES; MOLECULAR STRUCTURE; PHOSPHORIC ACIDS; PYRENES; SPECTROPHOTOMETRY; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 56449101031     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806747h     Document Type: Article

References (46)

1. Langhals, H. Helv. Chim. Acta 2005, 88, 1309-1343.
2. Würthner, F. Chem. Commun. 2004, 1564-1579.
3. Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259-15278.
4. Neuteboom, E. E.; Meskers, S. C. J.; Meijer, E. W.; Janssen, R. A. J. Macromol. Chem. Phys. 2004, 205, 217-222.
5. Wang, W.; Li, L. S.; Helms, G.; Zhou, H. H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
6. Ahrens, M. J.; Sinks, L. E.; Rybtchinski, B.; Liu, W. H.; Jones, B. A.; Giaimo, J. M.; Gusev, A. V.; Goshe, A. J.; Tiede, D. M.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 8284-8294.
7. Wang, H.; Kaiser, T. E.; Uemura, S.; Würthner, F. Chem. Commun. 2008, 1181-1183.
8. Bevers, S.; Schutte, S.; McLaughlin, L. W. J. Am. Chem. Soc. 2000, 122, 5905-5915.
9. Wang, W.; Wan, W.; Zhou, H. H.; Niu, S. Q.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 5248-5249.
10. Zheng, Y.; Long, H.; Schatz, G. C.; Lewis, F. D. Chem. Commun. 2005, 4795-4797.
11. Zheng, Y.; Long, H.; Schatz, G. C.; Lewis, F. D. Chem. Commun. 2006, 3830-3832.
12. Lewis, F. D.; Zhang, L. G.; Kelley, R. F.; McCamant, D.; Wasielewski, M. R. Tetrahedron 2007, 63, 3457-3464.
13. Rahe, N.; Rinn, C.; Carell, T. Chem. Commun. 2003, 2119-2121.
14. Clark, A. E.; Qin, C. Y.; Li, A. D. Q. J. Am. Chem. Soc. 2007, 129, 7586-7595.
15. Baumstark, D.; Wagenknecht, H. A. Angew. Chem., Int. Ed. 2008, 47, 2612-2614.
16. Wang, W.; Han, J. J.; Wang, L. Q.; Li, L. S.; Shaw, W. J.; Li, A. D. Q. Nano Lett. 2003, 3, 455-458.
17. Zhu, L. Y.; Wu, W. W.; Zhu, M. Q.; Han, J. J.; Hurst, J. K.; Li, A. D. Q. J. Am. Chem. Soc. 2007, 129, 3524-3526.
18. Giaimo, J. M.; Lockard, J. V.; Sinks, L. E.; Scott, A. M.; Wilson, T. M.; Wasielewski, M. R. J. Phys. Chem. A 2008, 112, 2322-2330.
19. Wagner, C.; Wagenknecht, H. A. Org. Lett. 2006, 8, 4191-4194.
20. Bouquin, N.; Malinovskii, V. L.; Häner, R. Chem. Commun. 2008, 1974-1976.
21. Malakhov, A. D.; Skorobogatyi, M. V.; Prokhorenko, I. A.; Gontarev, S. V.; Kozhich, D. T.; Stetsenko, D. A.; Stepanova, I. A.; Shenkarev, Z. O.; Berlin, Y. A.; Korshun, V. A. Eur. J. Org. Chem. 2004, 1298-1307.
22. Huang, T. H.; Chen, Y. J.; Lo, S. S.; Yen, W. N.; Mai, C. L.; Kuo, M. C.; Yeh, C. Y. Dalton Trans. 2006, 2207-2213. (and references cited therein).
23. Venkataramana, G.; Sankararaman, S. Eur. J. Org. Chem. 2005, 4162-4166.
24. Malinovskii, V. L.; Häner, R. Eur. J. Org. Chem. 2006, 3550-3553.
25. Maeda, H.; Maeda, T.; Mizuno, K.; Fujimoto, K.; Shimizu, H.; Inouye, M. Chem. - Eur. J. 2006, 12, 824-831.
26. Xiao, J. C.; Xu, J. L.; Cui, S.; Liu, H. B.; Wang, S.; Li, Y. L. Org. Lett. 2008, 10, 645-648.
27. Langenegger, S. M.; Häner, R. Chem. Commun. 2004, 2792-2793.
28. Langenegger, S. M.; Häner, R. ChemBioChem 2005, 6, 848-851.
29. Langenegger, S. M.; Häner, R. Bioorg. Med. Chem. Lett. 2006, 16, 5062-5065.
30. Trkulja, I.; Häner, R. J. Am. Chem. Soc. 2007, 129, 7982-7989.
31. Trkulja, I.; Häner, R. Bioconjugate Chem. 2007, 18, 289-292.
32. Malinovskii, V. L.; Samain, F.; Häner, R. Angew. Chem., Int. Ed. 2007, 46, 4464-4467.
33. Trkulja, I.; Biner, S. M.; Langenegger, S. M.; Häner, R. ChemBioChem 2007, 8, 25-27.
34. Looser, V.; Langenegger, S. M.; Häner, R.; Hartig, J. S. Chem. Commun. 2007, 4357-4359.
35. Werder, S.; Malinovskii, V. L.; Häner, R. Org. Lett. 2008, 10, 2011-2014.
36. Grimshaw, J.; Trochagr, J. J. Chem. Soc., Perkin Trans. 1 1972, 1622-1623.
37. Recently, the isolation of the 1,6-isomer from an isomeric mixture has been reported: Arai, R.; Uemura, S.; Irie, M.; Matsuda, K. J. Am. Chem. Soc. 2008, 130, 9371-9379.
38. Shyamala, T.; Sankararaman, S.; Mishra, A. K. Chem. Phys. 2006, 330, 469-477.
39. Benniston, A. C.; Harriman, A.; Howell, S. L.; Sams, C. A.; Zhi, Y. G. Chem. - Eur. J. 2007, 13, 4665-4674 (and references cited therein).
40. For a recent example in which hysteresis is ascribed to hydrogen bonding and hydrophobicity acting in a nonconcerted way, see: Sorrells, J. L.; Menger, F. M. J. Am. Chem. Soc. 2008, 130, 10072-10073.
41. Berova, N.; Nakanishi, K.; Woody, R. W. Circular Dichroism - Principles and Applications; Wiley-VCH: New York, 2000.
42. Boiadjiev, S. E.; Lightner, D. A. Monatsh. Chem. 2005, 136, 489-508.
43. Lewis, F. D.; Zhang, L. G.; Liu, X. Y.; Zuo, X. B.; Tiede, D. M.; Long, H.; Schatz, G. C. J. Am. Chem. Soc. 2005, 127, 14445-14453.
44. Ranasinghe, R. T.; Brown, T. Chem. Commun. 2005, 5487-5502.
45. Cuppoletti, A.; Cho, Y. J.; Park, J. S.; Strassler, C.; Kool, E. T. Bioconjugate Chem. 2005, 16, 528-534.
46. Venkatesan, N.; Seo, Y. J.; Kim, B. H. Chem. Soc. Rev. 2008, 37, 648-663.