On/off switching of perylene tetracarboxylic bisimide luminescence by means of substitution at the N-position by electron-rich mono-, Di-, and trimethoxybenzenes

Chemistry - A European Journal

Volumn 16, Issue 45, 2010, Pages 13406-13416

  Flamigni, Lucia ^a   Ventura, Barbara ^a   Barbieri, Andrea ^a   Langhals, Heinz ^b   Wetzel, Fritz ^b   Fuchs, Kerstin ^b   Walter, Andreas ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

bisimides; charge separation; electron transfer; luminescence; supramolecular chemistry

Indexed keywords

BISIMIDES; CHARGE SEPARATIONS; CHARGE-SEPARATED STATE; ELECTRON TRANSFER; ELECTRON-RICH; EMISSION QUANTUM YIELD; LUMINESCENCE PROPERTIES; METHOXY GROUP; METHOXYBENZENE; MODEL COMPOUND; PERYLENE BISIMIDES; PERYLENE TETRACARBOXYLIC; PHOTO-INDUCED ELECTRON TRANSFER; PHOTOPHYSICAL PROPERTIES; QUANTUM-CHEMICAL CALCULATION; RADICAL ANIONS; REDOX POTENTIALS; SOLVENT EFFECTS; STRUCTURAL VARIATIONS; SUBSTITUTION PATTERNS; TIME-RESOLVED SPECTROSCOPIC TECHNIQUES;

ABSORPTION SPECTROSCOPY; FREE RADICAL REACTIONS; LUMINESCENCE; LUMINESCENCE OF INORGANIC SOLIDS; MACROMOLECULES; QUANTUM CHEMISTRY; QUANTUM YIELD; QUENCHING; REDOX REACTIONS; SUPRAMOLECULAR CHEMISTRY;

ELECTRON TRANSITIONS;

EID: 78649879412     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001489     Document Type: Article

References (56)

1. See the following reviews and references therein
2. A. P. dea Silva, T. S. Moody, G. D. Wright, Analyst 2009, 134, 2385-2393
3. T. Gunnlaugsson, M. Glynn, G. M. Tocci, P. E. Kruger, F. M. Pfeffer, Coord. Chem. Rev. 2006, 250, 3094-3117
4. C. W. Rogers, M. O. Wolf, Coord. Chem. Rev. 2002, 233, 341-350.
5. See the following reviews and references therein
6. A. Credi, Angew. Chem. 2007, 119, 5568-5572
7. Angew. Chem. Int. Ed. 2007, 46, 5472-5475
8. A. P. dea Silva, S. Uchiyama, Nat. Nanotechnol. 2007, 2, 399-410
9. A. P. dea Silva, T. P. Vance, M. E. S. West, G. D. Wright, Org. Biomol. Chem. 2008, 6, 2468-2481.
10. H. Langhals, Helv. Chim. Acta 2005, 88, 1309-1343
11. H. Langhals, Heterocycles 1995, 40, 477-500
12. H. Langhals, Molecular Devices. Chiral Bichromophoric Silicones: Ordering Principles in Complex Molecules in Silicon Based Polymers (Eds.,. F. Ganachaud, S. Boileau, B. Boury,), Springer, Heidelberg, 2008, pp. 51-63.
13. H. Langhals, J. Karolin, L. B.-Å. Johansson, J. Chem. Soc. Faraday Trans. 1998, 94, 2919-2922.
14. H. Langhals, A. J. Esterbauer, Chem. Eur. J. 2009, 15, 4793-4796
15. F. Würthner, Chem. Commun. 2004, 1564-1579
16. F. Ilhan, D. S. Tyson, D. J. Stasko, K. Kirschbaum, M. A. Meador, J. Am. Chem. Soc. 2006, 128, 702-703
17. S. Vajiravelu, L. Ramunas, G. J. Vidas, G. Valentas, J. Vygintas, S. Valiyaveettil, J. Mater. Chem. 2009, 19, 4268-4275
18. J. Fortage, M. Séverac, C. Houarner-Rassin, Y. Pellegrin, E. Blart, F. Odobel, J. Photochem. Photobiol. A 2008, 197, 156-169
19. H. Langhals, A. Obermeier, Eur. J. Org. Chem. 2008, 6144-6151
20. H. Langhals, S. Poxleitner, O. Krotz, T. Pust, A. Walter, Eur. J. Org. Chem. 2008, 4559-4562.
21. H. Langhals, A Obermeier, Y. Floredo, A. Zanelli, L. Flamigni, Chem. Eur. J. 2009, 15, 12733-12744.
22. A. S. Lukas, Y. Zhao, S. E. Miller, M. R. Wasielewski, J. Phys. Chem. B 2002, 106, 1299-1306
23. F. Würthner, A. Sautter, D. Schmid, P. J. A. Weber, Chem. Eur. J. 2001, 7, 894-902
24. W. E. Ford, H. Hiratsuka, P. V. Kamat, J. Phys. Chem. 1989, 93, 6692-6696.
25. L. Flamigni, B. Ventura, M. Tasior, T. Becherer, H. Langhals, D. T. Gryko, Chem. Eur. J. 2008, 14, 169-183
26. L. Flamigni, B. Ventura, C.-C. You, C. Hippius, F. Würthner, J. Phys. Chem. C 2007, 111, 622-630
27. A. I. Oliva, B. Ventura, F. Würthner, A. Camara-Campos, C. A. Hunter, P. Ballester, L. Flamigni, Dalton Trans. 2009, 4023-4037
28. 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.
29. S. Xiao, Y. Li, Y. Li, J. Zhuang. N. Wang, H. liu, B. Ning, Y. liu, F. Lu, L. Fan, C. Yang, Y. Li, D. Zhu, J. Phys. Chem. B 2004, 108, 16677-16685
30. W. Xu, H. Chen, Y. Wang, C. Zhao, X. Li, S. Wang, Y. Weng, ChemPhysChem 2008, 9, 1409-1415
31. B. Rybtchinski, L. E. Sinks, M. R. Wasielewski, J. Am. Chem. Soc. 2004, 126, 12268-12269
32. C. Flors, I. Oesterling, T. Schnitzler, E. Fron, G. Schweitzer, M. Sliwa, A. Herrmann, M. vana dera Auweraer, F. C. dea Schryver, K. Müllen, J. Hofkens, J. Phys. Chem. C 2007, 111, 4861-4870
33. R. F. Kelley, W. S. Shin, B. Rybtchinski, L. E. Sinks, M. R. Wasielewski, J. Am. Chem. Soc. 2007, 129, 3173-3181
34. 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
35. M. J. Arhens, R. F. Kelley, Z. E. X. Dance, M. R. Wasielewski, Phys. Chem. Chem. Phys. 2007, 9, 1469-1478
36. A. Prodi, C. Chiorboli, F. Scandola, E. Iengo, E. Alessio, R. Dobrawa, F. Würthner, J. Am. Chem. Soc. 2005, 127, 1454-1462
37. F. J. Céspedez -Guirao, K. Ohkubo, S. Fukuzumi, A. Sastre-Santos, F. Fernández-Lázaro, J. Org. Chem. 2009, 74, 5871-5880
38. N. Vana Anh, F. Schlosser, M. M. Groeneveld, I. H. M. vana Stokkum, F. Würthner, R. Williams, J. Phys. Chem. C 2009, 113, 18358-18368.
39. H. Kaiser, J. Lindner, H. Langhals, Chem. Ber. 1991, 124, 529-535.
40. H. Langhals, Chem. Ber. 1985, 118, 4641-4645.
41. H. Langhals, S. Demmig, H. Huber, Spectrochim. Acta 1988, 44A, 1189-1193.
42. P. B. Merkel, P. Luo, J. P. Dinnocenzo, S. Farid, J. Org. Chem. 2009, 74, 5163-5173.
43. A. Zweig, W. G. Hodgson, W. H. Jura, J. Am. Chem. Soc. 1964, 86, 4124-4129.
44. M. Montalti, A. Credi, L. Prodi, M. T. Gandolfi, Handbook of Photochemistry, 3 rd ed., CRC Press, Boca Raton, 2006, pp. 624-627.
45. G. L. Gaines a III, M. P. O'Neil, W. A. Svec, M. P. Niemczyk, M. R. Wasielewski, J. Am. Chem. Soc. 1991, 113, 719-721
46. L. Flamigni, E. Baranoff, J.-P. Collin, J.-P. Sauvage, Chem. Eur. J. 2006, 12, 6592-6606.
47. W. E. Ford, P. V. Kamat, J. Phys. Chem. 1987, 91, 6373-6380.
48. 2. Given the level of approximation involved in the present discussion, we consider the simplification acceptable and convenient.
49. R. A. Marcus, Angew. Chem. 1993, 105, 1161-1172
50. Angew. Chem. Int. Ed. Engl. 1993, 32, 1111-1121, and references therein.
51. P. O'Neill, S. Steenken, D. Schulte-Frohlinde, J. Phys. Chem. 1975, 79, 2773-2779.
52. J. Salbeck, H. Kumkely, H. Langhals, R. W. Saalfrank, J. Daub, Chimia 1989, 43, 6-9
53. T. Kircher, H. G. Löhmannsröben, Phys. Chem. Chem. Phys. 1999, 1, 3987-3992.
54. A. A. Rachford, S. Goeb, F. N. Castellano, J. Am. Chem. Soc. 2008, 130, 2766-2767.
55. L. Flamigni, B. Ventura, A. I. Oliva, P. Ballester, Chem. Eur. J. 2008, 14, 4214-4224, and references therein.
56. 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.