Ultrafast photoinduced charge separation resulting from self-assembly of a green perylene-based dye into π-stacked arrays

Journal of Physical Chemistry A

Volumn 109, Issue 6, 2005, Pages 970-975

  Fuller, Michael J ^a   Sinks, Louise E ^a   Rybtchinski, Boris ^a   Giaimo, Jovan M ^a   Li, Xiyou ^a   Wasielewski, Michael R ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE SEPARATION; GREEN CHROMOPHORE; MONODISPERSE PENTAMERS; PHOTOINDUCED CHARGE GENERATION;

ABSORPTION SPECTROSCOPY; CONDENSATION; DIMERS; GROUND STATE; LIGHT ABSORPTION; ORGANIC COMPOUNDS; SELF ASSEMBLY; X RAY SCATTERING;

DYES;

EID: 14544280989     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp044796q     Document Type: Article

References (44)

1. Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; Mackenzie, J. D. Science 2001, 293, 1119-1122.
2. van de Craats, A. M.; Stutzmann, N.; Bunk, O.; Nielsen, M. M.; Watson, M.; Müllen, K.; Chanzy, H. D.; Sirringhaus, H.; Friend, R. H. Adv. Mater. 2003, 75, 495-499.
3. Schenning, A. P. H. J.; van Herrikhuyzen, J.; Jonkheijm, P.; Chen, Z.; Würthner, F.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 10252-10253.
4. Miura, A.; Chen, Z.; Uji-i, H.; De Feyter, S.; Zdanowska, M.; Jonkheijm, P.; Schenning, A. P. H. J.; Meijer, E. W.; Würthner, F.; De Schryver, F. C. J. Am. Chem. Soc. 2003, 725, 14968-14969.
5. Neuteboom, E. E.; Meskers, S. C. J.; Van Hal, P. A.; Van Duren, J. K. J.; Meijer, E. W.; Janssen, R. A. J.; Dupin, H.; Pourtois, G.; Cornil, J.; Lazzaroni, R.; Bredas, J.-L.; Beljonne, D. J. Am. Chem. Soc. 2003, 125, 8625-8638.
6. Neuteboom, E. E.; Meskers, S. C. J.; Meijer, E. W.; Janssen, R. A. J. Macromol. Chem. Phys. 2004, 205, 217-222.
7. van Herrikhuyzen, J.; Syamakumari, A.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2004, 126, 10021-10027.
8. Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. Eur. J. 2001, 7, 2245-2253.
9. Cormier, R.; Gregg, B. A. J. Phys. Chem. B 1997, 101, 11004-11006.
10. Cormier, R.; Gregg, B. A. Chem. Mater. 1998, 10, 1309-1319.
11. Gregg, B. A. J. Phys. Chem. B 2003, 707, 4688-4698.
12. Liu, S.-G.; Sui, G.; Cormier, R. A.; Leblanc, R. M.; Gregg, B. A. J. Phys. Chem. B 2002, 706, 1307-1315.
13. Struijk, C. W.; Sieval, A. B.; Dakhorst, J. E. J.; van Dijk, M.; Kimkes, P.; Koehorst, R. B. M.; Donker, H.; Schaafsma, T. J.; Picken, S. J.; van de Craats, A. M.; Warman, J. M.; Zuilhof, H.; Sudholter, E. J. R. J. Am. Chem. Soc. 2000, 722, 11057-11066.
14. Rohr, U.; Schlichting, P.; Böhm, A.; Gross, M.; Meerholz, K.; Bräuchte, C.; Müllen, K. Angew. Chem., Int. Ed. 1998, 37, 1434-1437.
15. Rohr, U.; Kohl, C.; Müllen, K.; van de Craats, A. M.; Warman, J. J. Mater. Chem. 2001, 11, 1789-1799.
16. Würthner, F.; Chen, Z.; Hoeben, F. J. M.; Osswald, P.; You, C.-C.; Jonkheijm, P.; Herrikhuyzen, J. v.; Schenning, A. P. H. J.; van der School. P. P. A. M.; Meijer, E. W.; Beckers, E. H. A.; Meskers, S. C. J.; Janssen, R. A. J. J. Am. Chem. Soc. 2004, 726, 10611-10618.
17. Ahrens, M. J.; Fuller, M. J.; Wasielewski, M. R. Chem. Mater. 2003, 15, 2684-2686.
18. Zhao, Y.; Wasielewski, M. R. Tetrahedron Lett. 1999, 40, 7047-7050.
19. Lukas, A. S.; Zhao, Y.; Miller, S. E.; Wasielewski, M. R. J. Phys. Chem. B 2002, 106, 1299-1306.
20. Giaimo, J. M.; Gusev, A. V.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 8530-8531.
21. Staab, H. A.; Riegler, N.; Diederich, F.; Krieger, C; Schweitzer, D. Chem. Ber. 1984, 117, 246-259.
22. Kang, T. J.; Kahlow, M. A.; Giser, D.; Swallen, S.; Nagarajan, V.; Jarzeba, W.; Barbara, P. F. J. Phys. Chem. 1988, 92, 6800-6807.
23. Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971-988.
24. Lathrop, E. J. P.; Friesner, R. A. J. Phys. Chem. 1994, 98, 3056-3066.
25. Won, Y.; Friesner, R. A. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 5511-5515.
26. Parson, W. W.; Scherz, A.; Warshel, A. Springer Ser. Chem. Phys. (Antennas React Cent. Photosynth. Bacteriol.) 1985, 42, 122-130.
27. Laporte, L. L.; Palaniappan, V.; Kirmaier, C.; Davis, D. G.; Schenck, C. C.; Holten, D.; Bocian, D. F. J. Phys. Chem. 1996, 100, 17696-17707.
28. Rybtchinski, B.; Sinks, L. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 12268-12269.
29. Percec, V.; Ahn, C.-R; Bera, T. K.; Ungar, G.; Yeardley, D. J. P. Chem. - Eur. J. 1999, 5, 1070-1083.
30. Seifert, S.; Winans, R. E.; Tiede, D. M.; Thiyagarajan, P. J. Appl. Crystallogr. 2000, 33, 782-784.
31. Guinier, A.; Fournet,G. Small Angle Scattering; Wiley: New York, 1955.
32. Svergun, D. I.; Koch, M. H. Rep. Prog. Phys. 2003, 66, 1735-1782.
33. Svergun, D. I. J. Appl. Crystallogr. 1992, 25, 495-503.
34. Svergun, D. I.; Semenyuk, A. V.; Feigin, L. A. Acta Crystallogr., Sect. A 1988, 44, 244-251.
35. Svergun, D. I. Biophys. J. 1999, 76, 2879-2886.
36. Volkov, V. V.; Svergun, D. I. J. Appl. Crystallogr. 2003, 36, 860-864.
37. Rybtchinski, B.; Sinks, L. E.; Wasielewski, M. R. J. Phys. Chem. A 2004, 108, 7497-7505.
38. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 311-392.
39. Glatter, O. In Neutron, X-ray and Light Scattering; Lindner, P., Zemb, T., Eds.; Elsevier. Amsterdam, 1991; pp 33-82.
40. Glatter, O.; Kratky, O. In Small-Angle X-ray Scattering; Academic Press: London, 1982.
41. Ahrens, M. J.; Sinks, L. E.; Rybtchinski, B.; Liu, W.; 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.
42. Li, X.; Sinks, L. E; Rybtchinski, B.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 10810-10811.
43. PM3 calculations were performed using HyperChem (TM). Hypercube Inc., 1115 NW 1114th Street, Gainesville, FL 32601.
44. Weller, A. Z. Phys. Chem. 1982, 133, 93-98.