Designing systems for a multiple use of light signals

ChemPhysChem

Volumn 5, Issue 3, 2004, Pages 315-320

  Bergamini, Giacomo ^a   Ceroni, Paola ^a   Balzani, Vincenzo ^a   Vögtle, Fritz ^b   Lee, Sang Kyu ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Benzophenon; Dendrimers; Energy transfer; Photochemistry; Sensitization

Indexed keywords

ABSTRACTING; ANTENNAS; DENDRIMERS; ENERGY TRANSFER; FLUORESCENCE; INFRARED DEVICES; PHOSPHORESCENCE; PHOTOCHEMICAL REACTIONS; QUENCHING;

BENZOPHENON; HYDROGEN ABSTRACTION REACTION; INTRAMOLECULAR HYDROGEN; PHOTOPHYSICAL BEHAVIOR; PHOTOPHYSICAL PROCESS; QUENCHING OF THE FLUORESCENCE; SENSITIZATION; SENSITIZED PHOSPHORESCENCE;

EXCITED STATES;

BENZENE DERIVATIVE; BENZOPHENONE; DENDRIMER; HYDROGEN;

ARTICLE; ENERGY TRANSFER; FLUORESCENCE; LIGHT; MOLECULAR INTERACTION; PHOSPHORESCENCE; PHOTOCHEMISTRY; PROCESS DESIGN; ULTRAVIOLET RADIATION;

EID: 2442652832     PISSN: 14394235     EISSN: None     Source Type: Journal    
DOI: 10.1002/cphc.200301076     Document Type: Article

References (82)

1. a) Topics in Current Chemistry: Dendrimers V (Eds.: F. Vögtle, C. Schalley), Springer Verlag, Berlin, 2003;
2. b) R. Newkome, C. Moorefield, F. Vögtle, Dendrimers and Dendrons: Concepts, Syntheses, Perspectives, VCH, Weinheim, 2001;
3. c) Dendrons and other dendritic polymers, (Eds.: J.M.J. Fréchet, D. A. Tomalia), Wiley, New York, 2001.
4. a) 3rd International Dendrimer Symposium, Book of Abstracts, September 17-20, 2003, Berlin/Germany;
5. b) S.-E. Stiriba, H. Frey, R. Haag, Angew. Chem. 1998, 110, 1385; Angew. Chem. Int. Ed. 2002, 41, 1329;
6. b) S.-E. Stiriba, H. Frey, R. Haag, Angew. Chem. 1998, 110, 1385; Angew. Chem. Int. Ed. 2002, 41, 1329;
7. c) B. Romagnoli, W. Hayes, J. Mater. Chem. 2002, 12, 767;
8. d) G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. 2001, 113, 1878; Angew. Chem. Int. Ed. 2001, 40, 1828;
9. d) G. E. Oosterom, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Angew. Chem. 2001, 113, 1878; Angew. Chem. Int. Ed. 2001, 40, 1828;
10. e) D. C. Tully, J. M. J. Fréchet, Chem. Commun. 2001, 1229;
11. f) S. Hecht, J. M. J. Fréchet, Angew. Chem. 2001, 113, 860; Angew. Chem. Int. Ed. 2001, 40, 74;
12. f) S. Hecht, J. M. J. Fréchet, Angew. Chem. 2001, 113, 860; Angew. Chem. Int. Ed. 2001, 40, 74;
13. g) A. D. Schlüter, J. P. Rabe, Angew. Chem. 2000, 112, 860; Angew. Chem. Int. Ed. 2000, 39, 864.
14. g) A. D. Schlüter, J. P. Rabe, Angew. Chem. 2000, 112, 860; Angew. Chem. Int. Ed. 2000, 39, 864.
15. For some leading reviews see: a) V. Balzani, P. Ceroni, M. Maestri, C. Saudan, V. Vicinelli, Top. Curr. Chem. 2003, 228, 159;
16. b) J.-F. Nierengarten, N. Armaroli, G. Accorsi, Y. Rio, J. F. Eckert, Chem. Eur. J. 2003, 9, 36;
17. c) D. Liu, S. De Feyter, M. Cotlet, A. Stefan, U.-M. Wiesler, A. Herrmann, D. Grebel-Koehler, J. Qu, K. Müllen, F. C. De Schryver, Macromolecules 2003, 36, 5918;
18. d) S. Campagna, C. Di Pietro, F. Loiseau, B. Maubert, N. McClenaghan, R. Passalacqua, F. Puntoriero, V. Ricevuto, S. Serroni, Coord. Chem. Rev. 2002, 229, 67;
19. e) V. Balzani, P. Ceroni, A. Juris, M. Venturi, S. Campagna, F. Puntoriero, S. Serroni, Coord. Chem. Rev. 2001, 219-221, 545;
20. f) A. Adronov, J. M. J. Fréchet, Chem. Commun. 2000, 1701.
21. For some recent papers see: a) S. Jordens, G. De Belder, M. Lor, G. Schweitzer, M. Van der Auweraer, T. Weil, E. Reuther, K. Müllen, F. C. De Schryver, Photochem. Photobiol. Sci. 2003, 2, 177;
22. b) U. Hahn, M. Gorka, F. Vögtle, V. Vicinelli, P. Ceroni, M. Maestri, V. Balzani, Angew. Chem. 2002, 114, 3747; Angew. Chem. Int. Ed. 2002, 41, 3595;
23. b) U. Hahn, M. Gorka, F. Vögtle, V. Vicinelli, P. Ceroni, M. Maestri, V. Balzani, Angew. Chem. 2002, 114, 3747; Angew. Chem. Int. Ed. 2002, 41, 3595;
24. c) V. Vicinelli, P. Ceroni, M. Maestri, V. Balzani, M. Gorka, F. Vögtle, J. Am. Chem. Soc. 2002, 124, 6461;
25. d) M.-S. Choi, T. Aida, T. Yamazaki, I. Yamazaki, Chem. Eur. J. 2002, 8, 2668;
26. e) J. M. Serin, D. W. Brousmiche, J. M. J. Fréchet, Chem. Commun. 2002, 2605;
27. f) E. M. Harth, S. Hecht, B. Helms, E. E. Malmstrom, J. M. J. Fréchet, C. J. Hawker, J. Am. Chem. Soc. 2002, 124, 3926;
28. g) M. Kimura, T. Shiba, M. Yamazaki, K. Hanabusa, H. Shirai, N. Kobayashi, J. Am. Chem. Soc. 2001, 123, 5636.
29. a) M.-H. Xu, J. Lin, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2002, 124, 14239;
30. b) V. J. Pugh, Q. S. Hu, X. Zuo, F. D. Lewis, L. Pu, J. Org. Chem. 2001, 66, 6136;
31. c) V. Balzani, P. Ceroni, S. Gestermann, C. Kauffmann, M. Gorka, F. Vögtle, Chem. Commun. 2000, 853.
32. a) T. H. Ghaddar, J. F. Wishart, D. W. Thompson, J. K. Whitesell, M. A. Fox, J. Am. Chem. Soc. 2002, 124, 8285;
33. b) C. S. Rajesh, G. J. Capitosti, S. J. Cramer, D. A. Modarelli, J. Phys. Chem. B 2001, 105, 10175;
34. c) P. Ceroni, V. Vicinelli, M. Maestri, V. Balzani, W.M. Müller, U. Müller, U. Hahn, F. Osswald, F. Vögtle, New J. Chem. 2001, 25, 989.
35. a) C. Saudan, V. Balzani, P. Ceroni, M. Gorka, M. Maestri, V. Vicinelli, F. Vögtle, Tetrahedron 2003, 59, 3845;
36. b) T. H. Ghaddar, J. K. Whitesell, M. A. Fox, J. Phys. Chem. B 2001, 105, 8729;
37. c) M. Maus, S. Mitra, M. Lor, J. Hofkens, T. Weil, A. Herrmann, K. Müllen, F. C. De Schryver, J. Phys. Chem. A 2001, 105, 3961;
38. d) L. Brauge, A.-M. Caminade, J.-P. Majoral, S. Slomkowski, M. Wolszczak, Macromolecules 2001, 34, 5599;
39. e) S. F. Swallen, Z. Zhu, J. S. Moore, R. Kopelman, J. Phys. Chem. B 2000, 104, 3988;
40. f) L. A. Baker, R. M. Crooks, Macromolecules 2000, 33, 9034.
41. a) D. Grebel-Koehler, D. Liu, S. De Feyter, V. Enkelmann, T. Weil, C. Engels, C. Samyn, K. Müllen, F. C. De Schryver, Macromolecules 2003, 36, 578;
42. b) J. Hayakawa, A. Momotake, T. Arai, Chem. Commun. 2003, 94;
43. c) M. Uda, A. Momotake, T. Arai, Org. Biomol. Chem. 2003, 1, 1635;
44. d) M. Imai, T. Arai, Tetrahedron Lett. 2002, 43, 5265;
45. e) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857.
46. a) R.-M. Sebastián, J.-C. Blais, A.-M. Caminade, J.-P. Majoral, Chem. Eur. J. 2002, 8, 2172;
47. b) S. Li, D. V. McGrath, J. Am. Chem. Soc. 2000, 122, 6795;
48. c) M. Drobizhev, A. Rebane, C. Sigel, E. H. Elandaloussi, C. W. Spangler, Chem. Phys. Lett. 2000, 375;
49. d) H. Meier, M. Lehmann, Angew. Chem. 1998, 110, 666; Angew. Chem. Int. Ed. 1998, 37, 643.
50. d) H. Meier, M. Lehmann, Angew. Chem. 1998, 110, 666; Angew. Chem. Int. Ed. 1998, 37, 643.
51. a) F. Vögtle, M. Gorka, R. Hesse, P. Ceroni, M. Maestri, V. Balzani, Photochem. Photobiol. Sci. 2002, 1, 45;
52. b) A. Dirksen, E. Zuidema, R. M. Williams, L. De Cola, C. Kauffmann, F. Vögtle, A. Roque, F. Pina, Macromolecules 2002, 35, 2743;
53. c) G. C. Dol, K. Tsuda, J.-W. Weener, M. J. Bartels, T. Asavei, T. Gensch, J. Hofkens, L. Latterini, A. P. H. J. Schenning, B. W. Meijer, F. C. De Schryver, Angew. Chem. 2001, 113, 1760; Angew. Chem. Int. Ed. 2001, 40, 1710;
54. c) G. C. Dol, K. Tsuda, J.-W. Weener, M. J. Bartels, T. Asavei, T. Gensch, J. Hofkens, L. Latterini, A. P. H. J. Schenning, B. W. Meijer, F. C. De Schryver, Angew. Chem. 2001, 113, 1760; Angew. Chem. Int. Ed. 2001, 40, 1710;
55. d) K. Tsuda, G. C. Dol, T. Gensch, J. Hofkens, L. Latterini, J. W. Weener, E. W. Meijer, F. C. De Schryver, J. Am. Chem. Soc. 2000, 122, 3445;
56. e) A. Archut, G. C. Azzellini, V. Balzani, L. De Cola, F. Vögtle, J. Am. Chem. Soc. 1998, 120, 12191;
57. f) A. Archut, F. Vögtle, L. De Cola, G. C. Azzellini, V. Balzani, P. S. Ramanujam, R. H. Berg, Chem. Eur. J. 1998, 4, 699.
58. a) A. Gilbert, J. Baggot, Essential of molecular photochemistry, Blackwell scientific publications, Oxford, 1991;
59. b) N.J. Turro, Modern Molecular Photochemistry, The Benjamin/Cummings Publishing Co., Menlo Park, 1978.
60. a) P. J. Wagner, R. J. Truman, A. E. Puchalski, R. Wake, J. Am. Chem. Soc. 1986, 108, 7727;
61. b) P. J. Wagner, R. J. Truman, J. C. Scaiano, J. Am. Chem. Soc. 1985, 107, 7093;
62. c) U. Pischel, S. Abad, L. R. Domingo, F. Boscá, M. A. Miranda, Angew. Chem. 2003, 115, 2635; Angew. Chem. Int. Ed. 2003, 42, 2531.
63. c) U. Pischel, S. Abad, L. R. Domingo, F. Boscá, M. A. Miranda, Angew. Chem. 2003, 115, 2635; Angew. Chem. Int. Ed. 2003, 42, 2531.
64. a) A. Beeby, L. M. Bushby, D. Maffeo, J. A. G. Williams, J. Chem. Soc. Perkin Trans. 2 2000, 1281;
65. b) M. H. V. Werts, M. A. Duin, J. W. Hofstraat, J. W. Verhoeven, Chem. Commun. 1999, 799;
66. c) A. P. Darmanyan, C. S. Foote, J. Phys. Chem. 1993, 97, 5032;
67. d) A. A. Lamola, P. A. Leermakers, G. W. Byers, G. S. Hammond, J. Am. Chem. Soc. 1965, 87, 2322.
68. S. Hecht, J. M. J. Fréchet, J. Am. Chem. Soc. 2001, 123, 6959.
69. D. R. Kearns, W. A. Case, J. Am. Chem. Soc. 1966, 88, 5087.
70. V. Balzani, A. Credi, M. Venturi, Chem. Eur. J. 2002, 8, 5525.
71. J. Saltiel, H. C. Curtis, L. Metts, J. W. Miley, J. Winterle, M. Wrighton, J. Am. Chem. Soc. 1970, 92, 410.
72. In deaerated acetonitrile solution benzophenone shows a phosphorescence band very similar to that of DMBP with τ = 70 μs.
73. J. Chilton, L. Giering, C. Steel, J. Am. Chem. Soc. 1976, 98, 1865.
74. a) P. J. Wagner, M. A. Meador, J. C. Scaiano, J. Am. Chem. Soc. 1984, 106, 7988;
75. b) E. F. Zwicker, L. I. Grossweiner, N. C. Yang, J. Am. Chem. Soc. 1963, 85, 2671.
76. C. Schweitzer, Z. Mehrdad, A. Noll, E.-W. Grabner, R. Schmidt, Helv. Chim. Acta 2001, 84, 2493.
77. 3+ emission is accompanied by the complete quenching of the benzophenone phosphorescence.
78. 3+ by the competing intramolecular photoreaction.
79. C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1990, 112, 7638.
80. J. N. Demas, G. A. Crosby, J. Phys. Chem. 1971, 75, 991.
81. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, Academic Press, London, 1965.
82. C. G. Hatchard, C. A. Parker, Proc. R. Soc. London Ser. A 1956, 235, 518.