Photophysical properties of cinchona organocatalysts in organic solvents

Journal of Physical Chemistry C

Volumn 113, Issue 27, 2009, Pages 11790-11795

  Qin, Wenwu ^a,b   Vozza, Alessandro ^a   Brouwer, Albert M ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION AND FLUORESCENCE SPECTROSCOPY; ACETONITRILE SOLUTIONS; AMINO GROUP; BROAD EMISSION BANDS; ELECTRON TRANSFER; EMISSION SPECTRUMS; LOCALLY EXCITED; LOCALLY EXCITED STATE; LONG WAVELENGTH BANDS; LONG-WAVELENGTH EMISSIONS; NON-POLAR SOLVENTS; ORGANOCATALYSTS; PHOTOPHYSICAL PROPERTIES; POLAR SOLVENTS; QUINOLINE RINGS; QUINUCLIDINE; STRONG ACIDS;

ABSORPTION SPECTROSCOPY; ACETONITRILE; AMINATION; AMINES; ELECTRON TRANSITIONS; FLUORESCENCE SPECTROSCOPY; ORGANIC SOLVENTS; PROTON TRANSFER; WAVELENGTH;

EMISSION SPECTROSCOPY;

EID: 67650799891     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp901867h     Document Type: Article

References (49)

1. Bredig, G.; Fiske, P. S. Biochem. Z. 1913, 46,1.
2. Hiemstra, H.; Wynberg, H. J. Am. Chem. Soc. 1981, 103, 411.
3. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley- VCH: Weinheim, Germany, 2005.
4. Li, H. M.; Wang, B. M.; Deng, L. J. Am. Chem. Soc. 2006, 128. 132.
5. Vakulya, B.; Varga, S.; Csampai, A.; Soos, T. Org. Lett. 2005, 7, 1961.
6. Wang, Y. Q.; Song, J.; Hong, R.; Li, H. M.; Deng, L. J. Am. Chem. Soc. 2006, 128, 8156.
7. Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
8. Li, H. M.; Wang, Y. Q.; Deng, L. Org. Lett. 2006, 8, 4063.
9. Bella, M.; Jorgensen, K. A. J. Am. Chem. Soc. 2004, 126, 5612.
10. Marcelli, T.; van der Haas, R. N. S.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 929.
11. Marcelli, T.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2006, 45, 1496.
12. Hammar, P.; Marcelli, T.; Hiemstra, H.; Himo, F. Adv. Synth. Catal. 2007, 349, 2531.
13. van Steenis, D.; Marcelli, T.; Lutz, M.; Spek, A. L.; van Maarse-veen, J. H.; Hiemstra, H. Adv. Synth. Catal. 2007, 349, 281.
14. Dondoni, A.; Massi, A. Angew. Chem., Int. Ed. 2008, 47, 4638.
15. Connon, S. J. Chem. Commun. 2008, 2499.
16. Bassan, A.; Zou, W. B.; Reyes, E.; Himo, F.; Cordova, A. Angew. Chem., Int. Ed. 2005, 44, 1028.
17. Fu, A. P.; List, B.; Thiel, W. J. Org. Chem. 2006, 71, 320.
18. Clemente, F. R.; Houk, K. N. Angew. Chem., Int. Ed. 2004, 43, 5166.
19. Lakowicz, J. R. Principlesof Fluorescence Spectroscopy, 3rd ed.; Springer-Verlag: New York, 2006.
20. Haugland, R. P. The Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 10th ed.; Molecular Probes, Inc: Eugene, OR, 2005.
21. Lakowicz, J. R. E. Topics in Fluorescence Spectroscopy, Vol. 1, Techniques; Plenum Press: New York, 1991.
22. Baeyens, W. G. R.; de Keukeleire, D.; Korkidis, K. Luminescence Techniques in Chemical and Biochemical Analysis; Marcel Dekker: New York, 1991.
23. Valeur, B. Molecular Fluorescence. Principles and Applications; Wiley-VCH: Weinheim, Germany, 2002.
24. Tanaka, F.; Thayumanavan, R.; Barbas, C. F. J. Am. Chem. Soc. 2003, 125, 8523.
25. Copeland, G. T.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 4306.
26. Stauffer, S. R.; Beare, N. A.; Stambuli, J. P.; Hartwig, J. F. J.Am. Chem. Soc. 2001, 123, 4641.
27. Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2611.
28. De Cremer, G.; Roeffaers, M. B. J.; Baruah, M.; Sliwa, M.; Sels, B. F.; Hofkens, J.; De Vos, D. E. J. Am. Chem. Soc. 2007, 129, 15458.
29. Martinez, V. M.; De Cremer, G.; Roeffaers, M. B. J.; Sliwa, M.; Baruah, M.; De Vos, D. E.; Hofkens, J.; Sels, B. F. J. Am. Chem. Soc. 2008, 130, 13192.
30. Xie, X. S.; Lu, H. P. J. Biol. Chem. 1999, 274, 15961.
31. Xie, X. S. J. Chem. Phys. 2002, 117, 11024.
32. Aloisi, G. G.; Barbafina, A.; Canton, M.; Dall'Acqua, F.; Elisei, F.; Facciolo, L.; Latterini, L.; Viola, G. Photochem. Photobiol. 2004, 79, 248.
33. Fletcher, A. N. J. Phys. Chem. 1968, 72, 2142.
34. Marcelli, T. Cinchona-derived organocatalysts for asymmetric carbon-carbon bond formation. Ph.D. Thesis, University of Amsterdam: Amsterdam, 2006.
35. Melhuish, W. H. J. Phys. Chem. 1961, 65, 229.
36. van Dijk, S. I.; Wiering, P. G.; Groen, C. P.; Brouwer, A. M.; Verhoeven, J. W.; Schuddeboom, W.; Warman, J. M. J. Chem. Soc. Faraday Trans. 1995, 91, 2101.
37. Pant, D.; Tripathi, H. B.; Pant, D. D. J. Photochem. Photobiol. A-Chem. 1991, 56, 201.
38. Mehata, M. S.; Joshi, H. C.; Tripathi, H. B. Chem. Phys. Lett. 2002, 359, 314.
39. Fu, Y.; Liu, L.; Yu, H. Z.; Wang, Y. M.; Guo, Q. X. J. Am. Chem. Soc. 2005, 127, 1221.
40. Mehata, M. S.; Joshi, H. C.; Tripathi, H. B. Chem. Phys. Lett. 2002, 366, 628.
41. Burgi, T.; Baiker, A. J. Am. Chem. Soc. 1998, 120, 12920.
42. Dijkstra, G. D. H.; Kellogg, R. M.; Wynberg, H.; Svendsen, J. S.; Marko, I.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 8069.
43. Hamza, A.; Schubert, G.; Soos, T.; Papai, I. J. Am. Chem. Soc. 2006, 128, 13151.
44. Poizat, O.; Bardez, E.; Buntinx, G.; Alain, V. J. Phys. Chem. A 2004, 108, 1813.
45. Pant, D.; Tripathi, H. B.; Pant, D. D. J. Lumin. 1991, 50, 249.
46. Meech, S. R.; Phillips, D. J. Photochem. 1983, 23, 193.
47. Velapoldi, R. A.; Mielenz, K. D. Standard Reference Materials: A Fluorescence Standard Reference Material: Quinine Sulfate Dihydrate; National Bureau of Standards Special Publication 260-64; National Bureau of Standards: Washington, DC, 1980 http://ts.nist.gov/MeasurementServices/ ReferenceMaterials/upload/SP260-64.pdf.
48. Pedros, J.; Porcar, I.; Gomez, C. M.; Campos, A.; Abad, C. Spectroc. Acta Part A 1997, 53, 421.
49. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X. N.; Takemoto, Y. J. Am. Chem. Soc. 2005, 127, 119.