Toward photoswitchable dendritic hosts. Interaction between azobenzene- functionalized dendrimers and eosin

Journal of the American Chemical Society

Volumn 120, Issue 47, 1998, Pages 12187-12191

  Archut, Andreas ^a   Azzellini, Gianluca Camillo ^b,c   Balzani, Vincenzo ^b   De Cola, Luisa ^b   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

AZOBENZENE; DENDRIMER; EOSIN;

ARTICLE; CHEMICAL REACTION; ELECTRON TRANSPORT; FLUORESCENCE; ISOMERISM; MOLECULAR DYNAMICS;

EID: 0032477319     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9822409     Document Type: Article

References (33)

1. Buhleier, E.; Wehner, W.; Vögtle, F. Synthesis 1978, 155.
2. '(3) (a) Newkome, G. R.; Moorefield, C.; Vögtle, F. Dendritic Macromolecules: Concepts, Syntheses, Perspectives; VCH: Weinheim, 1996.
3. (b) Tomalia, D. A.; Durst, H. D. Top. Curr. Chem. 1993, 165, 193.
4. (c) Gorman, C. Adv. Mater. 1998, 10, 295.
5. Jansen, J. F. G. A.; de Brabander-van der Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226.
6. (a) Fréchet, J. M. J. Science 1994, 263, 1710.
7. (b) Turro, C; Niu, S.; Bossmann, S. H.; Tomalia, D. A.; Turro, N. J. J. Phys. Chem. 1995, 99, 5512.
8. (c) Naylor, A. M.; Goddard, W. A., III; Kiefer, G. E.; Tomalia, D. A. J. Am. Chem. Soc. 1989. 111, 2339.
9. Jansen, J. F. G. A,; Meijer, E. W. J. Am. Chem. Soc. 1995, 117, 4417.
10. See also: Miklis, P.; Cagin, T.; Goddard, W. A., III. J. Am. Chem. Soc. 1997, 119, 7458.
11. Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, 1991. Balzani, V.; Scandola, F. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 10, p 687.
12. Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, 1991. Balzani, V.; Scandola, F. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 10, p 687.
13. Archut, A.; Vögtle, F.; De Cola, L.; Azzellini, G. C.; Balzani, V.; Ramanujam, P. S.; Berg, R. H. Chem. Eur. J. 1998, 4, 669.
14. (a) Rau, H. In Photochromism, Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 1990; Chapter 4.
15. (b) Kumar, G. S.; Neckers, D. C. Chem. Rev. 1989, 89, 1915.
16. (a) Shinkai, S.; Manabe, O. Top. Curr. Chem. 1984, 121, 67.
17. (b) Shinkai, S. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1, p 671.
18. (a) Junge, D. M.; McGrath, D. V. Chem. Commun. 1997, 857.
19. (b) Jiang, D.-L.; Aida, T. Nature 1997, 388, 454.
20. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry; Dekker: New Yok, 1993.
21. Ronayette, J.; Arnaud, R.; Lemaire, J. Can. J. Chem. 1974, 52, 1858.
22. A certain polydispersity, particularly of the higher generations originating from imperfections of the polyamine dendrimer skeletons, cannot be eliminated with the current workup procedures. MALDI-TOF mass spectroscopy does not show peaks that could be attributed to impurities originating from structural defects of the polyamine precursor or from incomplete conversion with the activated esters up to generation 3. In the case of generation 4 there are additional peaks below the molecule ion peak that originate from imperfect polyamine starting material, that is dendritic polyamines with less than 32 propylene amine arms in the periphery. For the sake of reliability of the photochemical investigations we have thus not extended our study to generation 5 azobenzene dendrimers. Structural defects in poly(propyleneimine) dendrimers have been investigated and categorized recently: Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Nepogodiev, S. A.; Meijer, E. W.; Peerlings, H. W. I; Stoddart, J. F. Chem. Eur. J. 1997, 3, 974. Hummelen, J. C.; van Dogen, J. L. J.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1493.
23. A certain polydispersity, particularly of the higher generations originating from imperfections of the polyamine dendrimer skeletons, cannot be eliminated with the current workup procedures. MALDI-TOF mass spectroscopy does not show peaks that could be attributed to impurities originating from structural defects of the polyamine precursor or from incomplete conversion with the activated esters up to generation 3. In the case of generation 4 there are additional peaks below the molecule ion peak that originate from imperfect polyamine starting material, that is dendritic polyamines with less than 32 propylene amine arms in the periphery. For the sake of reliability of the photochemical investigations we have thus not extended our study to generation 5 azobenzene dendrimers. Structural defects in poly(propyleneimine) dendrimers have been investigated and categorized recently: Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Nepogodiev, S. A.; Meijer, E. W.; Peerlings, H. W. I; Stoddart, J. F. Chem. Eur. J. 1997, 3, 974. Hummelen, J. C.; van Dogen, J. L. J.; Meijer, E. W. Chem. Eur. J. 1997, 3, 1493.
24. Valdes-Aguilera, O.; Neckers, D. C. Acc. Chem. Res. 1989, 22, 171.
25. Lakowicz, J. H. Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1986; Chapter 2.
26. Credi, A.; Prodi, L. Spectrochim. Acta A 1998, 54,159.
27. (a) Turro, N. J. Modern Molecular Photochemistry; Benjamin: Menlo Park, 1978.
28. (b) Gilbert, A.; Baggot, J. Essentials of Molecular Photochemistry; Blackwell: Oxford, 1991.
29. Moser, J.; Grätzel, M. J. Am. Chem. Soc. 1984, 106, 6567.
30. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-aqueous Systems; Dekker: New York, 1970.
31. 19 An equivalent equation can be written for the oxidative quenching.
32. Photosensitized oxidation of tertiary aliphatic amines by eosin has been observed: Bartholomeu, R. F.; Davidson, R. S. J. Chem. Soc. (C) 1971, 2347.
33. In the case of azobenzene, sensitization by triplet energy transfer is very efficient (Φ = 1) for the Z → and very inefficient (Φ = 0.015) for the E → Z reaction: Bortolus, P.; Monti, S. J. Phys. Chem. 1979, 83, 648.