Azobenzene-functionalized cascade molecules: Photoswitchable supramolecular systems

Chemistry - A European Journal

Volumn 4, Issue 4, 1998, Pages 699-706

  Archut, Andreas ^a   Vögtle, Fritz ^a   De Cola, Luisa ^b   Azzellini, Gianluca Camillo ^b,d   Balzani, Vincenzo ^a,b   Ramanujam, P S ^c   Berg, Rolf H ^c  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^d UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

Azo compounds; Dendrimers; Holographic data storage; Photochemistry; Supramolecular chemistry

Indexed keywords

EID: 0344836053     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19980416)4:4<699::aid-chem699>3.3.co;2-0     Document Type: Article

References (60)

1. G. R. Newkome, C. Moorefield, F. Vögtle, Dendritic Molecules: Concepts, Syntheses, Perspectives, VCH, Weinheim 1996, and references therein.
2. a) E. Buhleier, W. Wehner, F. Vögtle, Synthesis 1978, 155-158;
3. b) R. Moors, F. Vögtle, Chem. Ber. 1993, 126, 2133-2136;
4. c) C. Wörner, R. Mülhaupt, Angew. Chem. 1993, 105, 1367-1370; Angew. Chem. Int. Ed. Engl. 1993, 32, 1306-1308;
5. c) C. Wörner, R. Mülhaupt, Angew. Chem. 1993, 105, 1367-1370; Angew. Chem. Int. Ed. Engl. 1993, 32, 1306-1308;
6. d) E. M. M. de Brabander-van den Berg, E.W. Meijer, Angew. Chem. 1993, 105, 1370-1372; Angew. Chem., Int. Ed. Engl. 1993, 32, 1308-1310.
7. d) E. M. M. de Brabander-van den Berg, E.W. Meijer, Angew. Chem. 1993, 105, 1370-1372; Angew. Chem., Int. Ed. Engl. 1993, 32, 1308-1310.
8. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1991, 113, 4252-4261; C. J. Hawker, J. M. J. Fréchet, ibid. 1990, 112, 7638-7647.
9. K. L. Wooley, C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1991, 113, 4252-4261; C. J. Hawker, J. M. J. Fréchet, ibid. 1990, 112, 7638-7647.
10. D. A. Tomalia, H. Baker, J. R. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith, Polym. J. 1985, 17, 117-132; Macromolecules 1986, 19, 2466-2468.
11. D. A. Tomalia, H. Baker, J. R. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, P. Smith, Polym. J. 1985, 17, 117-132; Macromolecules 1986, 19, 2466-2468.
12. a) C. Kim, K. An, Bull. Korean Chem. Soc. 1997, 18, 164-170;
13. b) K. Lorenz, R. Mülhaupt, H. Frey, U. Rapp, F. J. Mayer-Posner, Macromolecules 1995, 28, 6657-6661;
14. c) D. Seyferth, D. Y. Son, A. L. Rheingold, R. L. Ostrander, Organometallics 1994, 13, 2682-2690;
15. d) A. W. van der Made, P. W. N. M. van Leeuwen, J. C. de Wilde, R. A. C. Brandes, Adv. Mater. 1993, 5, 466-468;
16. e) A. W. van der Made, P. W. N. M. van Leeuwen, J. Chem. Soc. Chem. Commun. 1992, 1400-1401.
17. a) N. Launay, A.-M. Caminade, R. Lahana, J.-P. Majorai, Angew. Chem. 1994, 106, 1682-1684; Angew. Chem. Int. Ed. Engl. 1994, 33, 1589-1592;
18. a) N. Launay, A.-M. Caminade, R. Lahana, J.-P. Majorai, Angew. Chem. 1994, 106, 1682-1684; Angew. Chem. Int. Ed. Engl. 1994, 33, 1589-1592;
19. b) M.-L. Lartigue, M. Slany, A.-M. Caminade, J.-P. Majoral, Chem. Eur. J. 1996, 2, 1417-1426.
20. S. Serroni, A. Juris, M. Venturi, S. Campagna, I. R. Resino, G. Denti, A. Credi, V. Balzani, J. Mater. Chem. 1997, 7, 1227-1236.
21. PAMAM dendrimers are available from Aldrich; poly(propylene imine) dendrimers can be obtained from the DSM corporation, Netherlands, and from Aldrich.
22. J. Issberner, R. Moors, F. Vögtle, Angew. Chem. 1994, 106, 2507-2514; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413-2420.
23. J. Issberner, R. Moors, F. Vögtle, Angew. Chem. 1994, 106, 2507-2514; Angew. Chem. Int. Ed. Engl. 1994, 33, 2413-2420.
24. a) For an introduction to nanotechnology see: K. E. Drexler, Nanosystems, Wiley-Interscience, New York, 1992; b) switchable devices in supramolecular chemistry: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim,1995; c) photochemical devices in supramolecular chemistry: V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester, 1991.
25. a) For an introduction to nanotechnology see: K. E. Drexler, Nanosystems, Wiley-Interscience, New York, 1992; b) switchable devices in supramolecular chemistry: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim,1995; c) photochemical devices in supramolecular chemistry: V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester, 1991.
26. a) For an introduction to nanotechnology see: K. E. Drexler, Nanosystems, Wiley-Interscience, New York, 1992; b) switchable devices in supramolecular chemistry: J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim,1995; c) photochemical devices in supramolecular chemistry: V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester, 1991.
27. H. Vennen, Hoechst High Chem Magazin 1994, 15, 57-59.
28. C. Bräuchle, N. Hampp, D. Oesterhelt, Adv. Mater. 1991, 3, 420-428.
29. For pertinent reviews see: a) S. Shinkai, O. Manabe, Topics Curr. Chem. 1984, 121, 67-104; b) G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915-1925; c) H. Rau in Photochromism, Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam 1990, chapter 4; V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester 1991, chapter 7.
30. For pertinent reviews see: a) S. Shinkai, O. Manabe, Topics Curr. Chem. 1984, 121, 67-104; b) G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915-1925; c) H. Rau in Photochromism, Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam 1990, chapter 4; V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester 1991, chapter 7.
31. For pertinent reviews see: a) S. Shinkai, O. Manabe, Topics Curr. Chem. 1984, 121, 67-104; b) G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915-1925; c) H. Rau in Photochromism, Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam 1990, chapter 4; V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester 1991, chapter 7.
32. For pertinent reviews see: a) S. Shinkai, O. Manabe, Topics Curr. Chem. 1984, 121, 67-104; b) G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915-1925; c) H. Rau in Photochromism, Molecules and Systems (Eds.: H. Dürr, H. Bouas-Laurent), Elsevier, Amsterdam 1990, chapter 4; V. Balzani, F. Scandola, Supramolecular Photochemistry, Horwood, Chichester 1991, chapter 7.
33. F. Würthner, J. Rebek, Jr., Angew. Chem. 1995, 107, 503-505; Angew. Chem. Int. Ed. Engl. 1995, 34, 446-448.
34. F. Würthner, J. Rebek, Jr., Angew. Chem. 1995, 107, 503-505; Angew. Chem. Int. Ed. Engl. 1995, 34, 446-448.
35. T. Ikeda, O. Tsutsumi, Science 1995, 268, 1873-1875.
36. M. Bauer, F. Vögtle, Chem. Ber. 1992, 125, 1675-1686.
37. K. T. Ranjit, S. Marx-Tibbon, I. Ben-Dov, I. Willner, Angew. Chem. 1997, 109, 91-93; Angew. Chem. Int. Ed. Engl. 1997, 36, 147-150;
38. K. T. Ranjit, S. Marx-Tibbon, I. Ben-Dov, I. Willner, Angew. Chem. 1997, 109, 91-93; Angew. Chem. Int. Ed. Engl. 1997, 36, 147-150;
39. S. Shinkai in: Comprehensive Supramolecular Chemistry, (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford, 1996.
40. S. Shinkai, K. Matsuo, A. Harada, O. Manabe, J. Chem. Soc. Perkin Trans. 2 1982, 1261-1265.
41. R. H. Berg, S. Hvilsted, P. S. Ramanujam, Nature 1996, 383, 505-508.
42. a) D. M. Junge, D. V. McGrath, Chem. Commun. 1997, 857-858;
43. b) M. Freemantle, Chem. Eng. News 1997, May 26, 30.
44. D.-L. Jiang, T. Aida, Nature 1997, 388, 454-456.
45. H.-B. Mekelburger, K. Rissanen, F. Vögtle, Chem. Ber. 1993, 126, 1161-1169.
46. P. Jacobson, Liebigs Ann. 1909, 367, 329; H. D. Anspon, Org. Synth. 1945, 25, 86-87; G. H. Coleman, G. Nichols, C. M. McCloskey, H. D. Anspon, ibid. 1945, 25, 87-89.
47. P. Jacobson, Liebigs Ann. 1909, 367, 329; H. D. Anspon, Org. Synth. 1945, 25, 86-87; G. H. Coleman, G. Nichols, C. M. McCloskey, H. D. Anspon, ibid. 1945, 25, 87-89.
48. P. Jacobson, Liebigs Ann. 1909, 367, 329; H. D. Anspon, Org. Synth. 1945, 25, 86-87; G. H. Coleman, G. Nichols, C. M. McCloskey, H. D. Anspon, ibid. 1945, 25, 87-89.
49. MALDI-TOF mass spectrometry 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 although these are now commercially available (see ref. [8]). Structural defects in poly(propylene imine) dendrimers have been investigated and categorized recently, cf.: a) P. R. Ashton, S. E. Boyd, C. L. Brown, S. A. Nepogodiev, E. W. Meijer, H. W. I. Peerlings, J. F. Stoddart, Chem. Eur. J. 1997, 3, 974-984;
50. b) J. C. Hummelen, J. L. J. van Dongen, E. W. Meijer, Chem. Eur. J. 1997, 3, 1489-1493.
51. Compare: P. Lange, A. Schier, H. Schmidbaur, Inorg. Chem. 1996, 35, 637-642.
52. A. Bencini, M. A. Bernardo, A. Bianchi, M. Ciampolini, V. Fusi, N. Nardi, A.-J. Parola, F. Pina, B. Valtancoli, J. Chem. Soc. Perkin Trans. 2, 1998, 413-418.
53. P. S. Ramanujam, N. C. R. Holme, S. Hvilsted, Appl. Phys. Lett. 1996, 68, 1329-1331.
54. P. Rochon, E. Batalla, A. Natansohn, Appl. Phys. Lett. 1995, 66, 136-138.
55. D. Y. Kim, S. K. Tripathy, L. Li, J. Kumar, Appl. Phys. Lett. 1995, 66, 1166-1168.
56. N. C. R. Holme, L. Nikolova, P. S. Ramanujam, S. Hvilsted, ibid., 1995, 70, 1518-1520.
57. P. Freundler, Bull. Soc. Chim. Fr. 1907, [4] 1, 221.
58. E. Fischer, EPA Newsletter 1984, 21, 33.
59. T. G. Pederson, P. M. Johansen, N. C. R. Holme, P. S. Ramanujam, S. Hvilsted, Phys. Rev. Lett. 1998, 80, 89-92.
60. W. Maier, A. Saupe, Z. Naturforsch. A 1959, 14, 882.