Water-soluble oligomer dimers based on paracyclophane: A new optical platform for fluorescent sensor applications

Journal of the American Chemical Society

Volumn 124, Issue 40, 2002, Pages 11868-11869

  Hong, Janice W ^a   Gaylord, Brent S ^b   Bazan, Guillermo C ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b University of California   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; OLIGOMER; PARACYCLOPHANE DERIVATIVE;

ARTICLE; CONJUGATION; FLUORESCENCE; LIGHT SCATTERING; MOLECULAR MECHANICS; OLIGOMERIZATION; PHOTOCHEMICAL QUENCHING; PHOTOLUMINESCENCE; POLYMERIZATION; SENSOR; SOLUBILITY; STRUCTURE ANALYSIS; SURFACE TENSION;

BIOSENSING TECHNIQUES; BRIDGED COMPOUNDS; ETHERS; FLUORESCENT DYES; LIGHT; POLYMERS; QUATERNARY AMMONIUM COMPOUNDS; SCATTERING, RADIATION; SOLUBILITY; SPECTROMETRY, FLUORESCENCE; SURFACE-ACTIVE AGENTS; WATER;

EID: 0037048718     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027170r     Document Type: Article

References (28)

1. (a) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
2. (b) Wosnick, J. H.; Swager, T. M. Curr. Opin. Chem. Biol. 2000. 100, 2537.
3. (c) Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.; Klewer Academic/Plenum Publishers: New York, 1999.
4. (d) Chen, L.; McBranch. D. W.; Wang, H.; Helgeson, R.; Wudl, F.; Whitten, D. G. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12287.
5. (a) Shi, S.; Wudl, F. Macromolecules 1990, 23, 3, 2119.
6. (b) Chen, L.; McBranch, D. W.; Wang, H. L.; Helgeson, R.; Wudl, F.; Whitten, D. G. Proc. Natl. Acad. Sci. U.S.A. 2000, 96, 12287.
7. Water solubility can also be achieved by incorporating pH-dependent functionalities, or polyether sidegroups. See: (a) McCullough, R. D.; Ewbank, P. C.; Loewe, R. S J. Am. Chem. Soc. 1997, 119, 63. (b) Kim, B. S.; Osada, Y. Korea Polym. J. 1999, 7, 350. (c) Aida, T.; Takemura, A.; Fuse, M.; Inoue, S. J. Chem. Soc., Chem. Commun. 1988, 3, 191. (d) Kiji, J.; Okano, T. Rev. Heteroat. Chem. 1994, 11, 191.
8. Water solubility can also be achieved by incorporating pH-dependent functionalities, or polyether sidegroups. See: (a) McCullough, R. D.; Ewbank, P. C.; Loewe, R. S J. Am. Chem. Soc. 1997, 119, 63. (b) Kim, B. S.; Osada, Y. Korea Polym. J. 1999, 7, 350. (c) Aida, T.; Takemura, A.; Fuse, M.; Inoue, S. J. Chem. Soc., Chem. Commun. 1988, 3, 191. (d) Kiji, J.; Okano, T. Rev. Heteroat. Chem. 1994, 11, 191.
9. Water solubility can also be achieved by incorporating pH-dependent functionalities, or polyether sidegroups. See: (a) McCullough, R. D.; Ewbank, P. C.; Loewe, R. S J. Am. Chem. Soc. 1997, 119, 63. (b) Kim, B. S.; Osada, Y. Korea Polym. J. 1999, 7, 350. (c) Aida, T.; Takemura, A.; Fuse, M.; Inoue, S. J. Chem. Soc., Chem. Commun. 1988, 3, 191. (d) Kiji, J.; Okano, T. Rev. Heteroat. Chem. 1994, 11, 191.
10. Water solubility can also be achieved by incorporating pH-dependent functionalities, or polyether sidegroups. See: (a) McCullough, R. D.; Ewbank, P. C.; Loewe, R. S J. Am. Chem. Soc. 1997, 119, 63. (b) Kim, B. S.; Osada, Y. Korea Polym. J. 1999, 7, 350. (c) Aida, T.; Takemura, A.; Fuse, M.; Inoue, S. J. Chem. Soc., Chem. Commun. 1988, 3, 191. (d) Kiji, J.; Okano, T. Rev. Heteroat. Chem. 1994, 11, 191.
11. Stork, M. S.; Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2001, 123, 6417.
12. DTA was chosen for comparison against other studies (see refs 6, 7).
13. Gaylord, B. S.; Wang, S.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2001, 123, 6417.
14. Chen, L.; Xu, S.; McBranch, D.; Whitten, D. J. Am. Chem. Soc. 2000, 122, 9302.
15. See also: Lakowicz, J. R. Anal. Biochem. 2001, 298, 1.
16. (a) Basic DNA and RNA Protocols; Harwood, A. J., Ed.; Humana Press: Totowa, NJ, 1996.
17. (b) Pattarkine, Mrunalini V.; Ganesh, Krishna N. Biochem. Biophys. Res. Commun. 1999, 263, 41.
18. Scholes, G. D. J. Phys. Chem. 1996, 100, 18731.
19. Wang, S.; Bazan, G. C.; Tretiak, S.; Mukamel, S. J. Am. Chem. Soc. 2000, 122, 1298.
20. Bazan, G. C.; Oldham, W. J., Jr.; Lachiocotte, R. J.; Tretiak, S.; Mukamel, S. J. Am. Chem. Soc. 1998, 120, 9188.
21. Voegtle, F. Cyclophane Chemistry; J. Wiley & Sons: New York, 1993.
22. Bartholomew, G. P.; Bazan, G. C. Acc. Chem. Rev. 2001, 34, 30.
23. For synthesis, see: Bartholomew, G. P.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 5182.
24. It is significant that the chromophore-building steps in Scheme 1 do not rely on a C-C bonding reaction in water. These tend to be problematic in circumstances were multiple attachments are required. See ref 6.
25. Using the Wyatt EOS MALS software package.
26. Relative to 9,10-diphenylanthracene. See: Maciejewski, A.; Steer, R. D. J. Photochem. 1986, 35, 59.
27. Wang, J.; Wang, D.; Miller, E. K.; Moses, D.; Bazan, G. C.; Heeger, A. J. Macromolecules 2000, 33, 5153.
28. 4Br and studies of 2 with an equimolar amount of NaBr), with results similar to those reported in Figure 2. See the Supporting Information.