Light-driven charge separation in isoxazolidine-perylene bisimide dyads

Chemistry - A European Journal

Volumn 15, Issue 46, 2009, Pages 12733-12744

  Langhals, Heinz ^a   Obermeier, Andreas ^a   Floredo, Yvonne ^a   Zanelli, Alberto ^b   Flamigni, Lucia ^b  

^a UNIVERSITY OF MUNICH   (Germany)

^b CNR   (Italy)

Author keywords

Charge separation; Charge transfer; Electron transfer; Photochemistry; Supramolecular chemistry

Indexed keywords

AMINO GROUP; CHARGE RECOMBINATION REACTIONS; CHARGE SEPARATION; CHARGE SEPARATIONS; CURRENT THEORIES; ELECTRON ACCEPTOR; ELECTRON DONORS; ELECTRON TRANSFER; ISOXAZOLIDINES; PERYLENE BISIMIDES; PERYLENE TETRACARBOXYLIC; SOLVENT POLARITY;

AMINES; CHARGE TRANSFER; CHROMOPHORES; DICHLOROMETHANE; ELECTRON TRANSITIONS; FLUORINE CONTAINING POLYMERS; ION EXCHANGE; MACROMOLECULES; MASS TRANSFER; SOLVENTS; TOLUENE;

SUPRAMOLECULAR CHEMISTRY;

EID: 71549118833     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901839     Document Type: Article

References (56)

1. a) C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 2001, 11, 15-26;
2. b) S. Günes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 207, 1324-1338.
3. a) M. Grätzel, Nature 2001, 414, 338-344;
4. b) H. Choi, S. Kim, S. O. Kang, J. Ko. M, -S. Kang, J. N. Clifford, A. Forneli, E. Palomares, M. K. Nazeeruddin, M. Grätzel, Angew. Chem. 2008, 120, 8383-8387;
5. Angew. Chem. Int. Ed. 2008, 47, 8259-8263;
6. c)F. Gao, Y. Wang, D. Shi, J. Zhang, M. Wang, X. Jing, R. Humphry-Baker, P. Wang, S. M. Zakeeruddin, M. Grätzel, J. Am. Chem. Soc. 2008, 130, 10720-10728.
7. a) D. Gust, T. A. Moore, A. L. Moore, Acc. Chem Res. 2001, 34, 40-48;
8. b) M. R. Wasielewski, J. Org. Chem. 2006, 71, 5051-5066.
9. a) H. Langhals, Helv. Chim. Acta 2005, 88, 1309-1343;
10. b) H. Langhals, Heterocycles 1995, 40, 477-500;
11. c)"Molecular Devices. Chiral, Bichromophoric Silicones: Ordering Principles in Complex Molecules": H. Langhals in Silicon Based Polymers (Eds.: F. Ganachaud, S. Boileau, B. Boury), Springer, Heidelberg, 2008, pp. 51-63.
12. H. Langhals, J. Karolin, L. B.-Å. Johansson, J. Chem. Soc. Faraday Trans 1998, 94, 2919-2922.
13. a) W. E. Ford, H. Hiratsuka, P. V Kamat, J. Phys. Chem. 1989, 93, 6692-6696;
14. b) F. Würthner, Chem. Commun. 2004, 1564-1579;
15. c) B. Rybtchinski, L. E. Sinks, M. R. Wasielewski, J. Am. Chem. Soc. 2004, 126, 12268-12269;
16. d) C. Flors, I. Oesterling, T. Schnitzler, E. Fron, G. Schweitzer, M. Sliwa, A. Herrmann, M. van der Auweraer, F. C. de Schryver, K. Müllen, J. Hofkens, J. Phys. Chem. C 2007, 111, 4861-4870;
17. e) R. E. Kelley, W. S. Shin, B. Rybtchinski, L. E. Sinks, M. R. Wasielewski, J. Am. Chem. Soc. 2007, 129, 3173-3181;
18. f) S. I. Yang, S. Prathapan, M. A. Miller, J. Seth, D. F Bocian, J. S. Lindsey, D. Holten, J. Phys Chem. B 2001, 105, 8249-8258;
19. g) M. J. Arhens, R. F. Kelley, Z. E. X. Dance, M. R. Wasielewski, Phys. Chem. Chem. Phys 2007, 9, 1469-1478;
20. h) A. Prodi, C. Chiorboli, F. Scandola, E. Iengo, E. Alessio, R. Dobrawa, F. Würthner, J. Am. Chem. Soc. 2005, 127, 1454-1462.
21. a) A. S. Lukas, Y. Zhao, S. E. Miller, M. R. Wasielewski, J. Phys. Chem. B 2002, 106, 1299-1306;
22. b)E. Würthner, A. Sautter, D. Schmid, P. J. A. Weber, Chem. Eur. J. 2001, 7, 894-902.
23. a) L. Flamigni, B. Ventura, M. Tasior, T. Becherer, H. Langhals, D. T. Gryko, Chem. Eur. J. 2008, 14, 169-183;
24. b) L. Flamigni, B. Ventura, C-C You, C Hippius, F Würthner, J. Phys. Chem. C 2007, 111, 622-630;
25. c) A. I. Oliva, B. Ventura, F Würthner, A. CamaraCampos, C. A. Hunter, P. Ballester, L. Flamigni, Dalton Trans. 2009, 4023-4037.
26. a) H. Langhals, W. Jona, Chem. Eur. J. 1998, 4, 2110-2116;
27. b) G. J. Mohr, U. E. Spichiger, W. Jona, H. Langhals, Anal. Chem. 2000, 72, 1084-1087.
28. H. Langhals, A. Obermeier, Eur. J. Org. Chem. 2008, 6144-6155.
29. H. Langhals, P. Blanke, Dyes Pigm. 2003, 59, 109-116.
30. H. Langhals, T. Becherer, J. Lindner, A. Obermeier, Eur. J. Org. Chem. 2007, 4328-4336.
31. a) R. Huisgen, R. Grashey, H. Hauck, H. Seidl, Chem. Ber. 1968, 101, 2548-2558;
32. b) R. Grashey, R. Huisgen, H. Leitermann, Tetrahedron Lett. 1960, 2, 9-13;
33. c) C. W. Brown, K. Marsden, M. T. A. Rogers, C. M. B. Taylor, R. Wright, Proc. Chem. Soc. 1960, 254-255;
34. d) G. R. Delpierre, M. Lamchen, Proc. Chem. Soc. 1960, 386-387.
35. R. Huisgen, R. Grashey, H. Hauck, H. Seidl, Chem. Ber. 1968, 101, 2568-2584.
36. H. Langhals, S. Demmig, H. Huber, Spedrochim. Acta 1988, 44, 1189-1193.
37. a) G. L. Gaines III, M. P. O'Neil, W. A. Svec, M. P. Niemczyk, M. R. Wasielewski, J. Am. Chem. Soc. 1991, 113, 719 -721;
38. b) L. Flamigni, E. Baranoff, J.-P. Collin, J.-P. Sauvage, Chem. Eur. J. 2006, 12, 6592-6606.
39. a) J. Salbeck, H. Kumkely, H. Langhals, R. W. Saalfrank, J. Daub, Chimia 1989, 43, 6-9;
40. b) T. Kircher, H. G. Löhmannsröben, Phys. Chem. Chem. Phys. 1999, 2, 3987-3992.
41. 2 is used to ensure oxidation of IA.
42. J. Gritzner, J. Kuta, Pure Appl. Chem. 1984, 56, 461-466.
43. a) L. Segura, R. Gomez , E. Reinold, Org. Lett. 2005, 7, 2345-2348;
44. b) M. Tasior, D. T. Gryko, J. Shen, K. M. Kadish, T. Becherer, H. Langhals, B. Ventura, L. Flamigni, J. Phys. Chem. C 2008, 112, 19699-19709.
45. S. K. Lee, Y. Zu, A. Hermann, Y. Geerts, K. Mullen, A. J. Bard, J. Am. Chem. Soc. 1999, 121, 3513-3520.
46. A. Weiler, Z. Phys. Chem. (Muenchen Ger.) 1982, 133, 93-98.
47. D = 3.5 ̊
48. a) N Mataga, H . Chosrowjan, S. Taniguchi, Y. Shibata, N. Yoshida, A Osuka, T. Kikuzawa, T. Okada, J. Phys. Chem. A 2002, 106, 12191-12201;
49. b) M. Tasior, D. T. Gryko, M. Cembor, J. S. Jaworski, B. Ventura, L. Flamigni, New J. Chem. 2007, 31, 247-259.
50. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172;
51. Angew. Chem. Int. Ed. Engl. 1993, 32,1111-1121, and references therein.
52. W. Korytnyk, N Angelino, C. Dave, L. Caballas, J. Med. Chem. 1978, 21, 507-513.
53. L. Flamigni, B. Ventura, A. I. Oliva, P. Ballester, Chem. Eur. J. 2008, 14, 4214-4224, and references therein.
54. L. Flamigni, A. M. Talarico, S. Serroni, F. Puntoriero, M. J. Gunter, M. R. Johnston, T. P. Jeynes, Chem. Eur. J. 2003, 9, 2649-2659, and references therein.
55. L. Flamigni, J. Phys Chem. 1992, 96, 3331-3337.
56. CS Chem. 3D Ultra CambridgeSoft. Com, Cambridge MA, USA, 2000.