Pt(II)-directed self-assembly of a dinuclear cyclophane containing two fullerenes

Angewandte Chemie - International Edition

Volumn 37, Issue 13-14, 1998, Pages 1916-1919

  Habicher, Tilo ^a   Nierengarten, Jean François ^b   Gramlich, Volker ^a   Diederich, François ^a  

^a ETH ZURICH   (Switzerland)

^b INSTITUT DE PHYSIQUE ET CHIMIE DES MATÉRIAUX DE STRASBOURG   (France)

Author keywords

Cyclophanes; Fullerenes; N ligands; Platinum; Supramolecular chemistry

Indexed keywords

EID: 0032479773     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980803)37:13/14<1916::AID-ANIE1916<3.0.CO;2-E     Document Type: Article

References (45)

1. a) C. A. Mirkin, W. B. Caldwell, Tetrahedron 1996, 52, 5113-5130;
2. b) M. Prato, J. Mater. Chem. 1997, 7, 1097-1109;
3. c) H. Imahori, Y. Sakata, Adv. Mater. 1997, 9, 537-546.
4. a) F. Diederich, C. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, J. Chem. Soc. Chem. Commun. 1995, 781-782;
5. b) N. Armaroli, F. Diederich, C. O. Dietrich Buchecker, L. Flamigni, G. Marconi, J.-F. Nierengarten, J.-P. Sauvage, Chem. Eur. J. 1998, 4, 406-416.
6. P. R. Ashton, F. Diederich, M. Gómez-López, J.-F. Nierengarten, J. A. Preece, F. M. Raymo, J. F. Stoddart, Angew. Chem. 1997,109, 1611-1614; Angew. Chem. Int. Ed. Engl. 1997, 36, 1448-1451.
7. P. R. Ashton, F. Diederich, M. Gómez-López, J.-F. Nierengarten, J. A. Preece, F. M. Raymo, J. F. Stoddart, Angew. Chem. 1997,109, 1611-1614; Angew. Chem. Int. Ed. Engl. 1997, 36, 1448-1451.
8. a) M. Maggini, A. Donò, G. Scorrano, M. Prato, J: Chem. Soc. Chem. Commun. 1995, 845-846;
9. b) D. Armspach, E. C. Constable, F. Diederich, C. E. Housecroft, J.-F. Nierengarten, Chem. Commun. 1996, 2009-2010;
10. c) D. Armspach, E. C. Constable, F. Diederich, C. E. Housecroft, J.-F. Nierengarten, Chem. Eur. J. 1998, 4, 723-733.
11. a) J.-M. Lehn, Supramolecular Chemistry-Concepts and Perspectives, VCH, Weinheim, 1995, pp. 139-197;
12. b) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-F. Nierengarten, J.-P. Sauvage, Pure Appl. Chem. 1994, 66, 1543-1550.
13. a) M. Fujita, J. Yazaki, K. Ogura, J. Am. Chem. Soc. 1990, 112, 5645-5647;
14. b) M. Fujita, S. Nagao, M. Iida, K. Ogata, K. Ogura, J. Am. Chem. Soc. 1993, 115, 1574-1576.
15. For reviews on molecular squares see a) P. J. Stang, Chem. Eur. J. 1998, 4, 19-27; b) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 502-518.
16. For reviews on molecular squares see a) P. J. Stang, Chem. Eur. J. 1998, 4, 19-27; b) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 502-518.
17. a) P. J. Stang, D. H. Cao, S. Saito, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 6273-6283;
18. b) P. J. Stang, K. Chen, A. M. Arif, J. Am. Chem. Soc. 1995, 117, 8793-8797;
19. c) B. Olenyuk, J. A. Whiteford, P. J. Stang, J. Am. Chem. Soc. 1996, 118, 8221-8230;
20. d) P. J. Stang, B. Olenyuk, J. Fan, A. M. Arif, Organometaltics 1996, 15, 904-908;
21. e) J. A. Whiteford, C. V. Lu, P. J. Stang, J. Am. Chem. Soc. 1997, 119, 2524-2533;
22. f) P. J. Stang, D. H. Cao, K. Chen, G. M. Gray, D. C. Muddiman, R. D. Smith, J. Am. Chem. Soc. 1997, 119, 5163-5168.
23. a) A. W. Schwabacher, J. Lee, H. Lei, J. Am. Chem. Soc. 1992, 114, 7597-7598;
24. b) H. Rauter, E. C. Hillgeris, A. Erxleben, B. Lippert, J. Am. Chem. Soc. 1994, 116, 616-624;
25. c) C. M. Drain, J.-M. Lehn, J. Chem. Soc. Chem. Commun. 1994, 2313-2315;
26. d) R. V. Slone, J. T. Hupp, C. L. Stern, T. E. Albrecht-Schmitt, Inorg. Chem. 1996, 35, 4096-4097.
27. a) M. Fujita, S. Nagao, K. Ogura, J. Am. Chem. Soc. 1995, 117, 1649-1650;
28. b) M. Fujita, D. Oguro, M. Miyazawa, H. Oka, K. Yamaguchi, K. Ogura, Nature 1995, 378, 469-471;
29. c) M. Fujita, M. Aoyagi, F. Ibukuro, K. Ogura, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 611-612;
30. d) P. J. Stang, B. Olenyuk, Organometallics 1997, 16, 3094-3096.
31. F. L. Minn, C. L. Trichilo, C. R. Hurt, N. Filipescu, J. Am. Chem. Soc. 1970, 92, 3600-3610.
32. C. Bingel, Chem. Ber. 1993, 126, 1957-1959.
33. 13C NMR, IR, and UV/Vis spectroscopies, FAB or MALDI-TOF-MS, and elemental analysis.
34. For hexakis(methano)fullerenes, see a) L. Isaacs, R. F. Haldimann, F. Diederich, Angew, Chem. 1994, 106, 2434-2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2339-2342; b) P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 1996, 79, 1047-1058; c) L. Isaacs, F. Diederich, R. F. Haldimann, Helv. Chim. Acta 1997, 80, 317-342; d) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385-9386; e) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, 52, 5065-5075.
35. For hexakis(methano)fullerenes, see a) L. Isaacs, R. F. Haldimann, F. Diederich, Angew, Chem. 1994, 106, 2434-2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2339-2342; b) P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 1996, 79, 1047-1058; c) L. Isaacs, F. Diederich, R. F. Haldimann, Helv. Chim. Acta 1997, 80, 317-342; d) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385-9386; e) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, 52, 5065-5075.
36. For hexakis(methano)fullerenes, see a) L. Isaacs, R. F. Haldimann, F. Diederich, Angew, Chem. 1994, 106, 2434-2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2339-2342; b) P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 1996, 79, 1047-1058; c) L. Isaacs, F. Diederich, R. F. Haldimann, Helv. Chim. Acta 1997, 80, 317-342; d) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385-9386; e) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, 52, 5065-5075.
37. For hexakis(methano)fullerenes, see a) L. Isaacs, R. F. Haldimann, F. Diederich, Angew, Chem. 1994, 106, 2434-2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2339-2342; b) P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 1996, 79, 1047-1058; c) L. Isaacs, F. Diederich, R. F. Haldimann, Helv. Chim. Acta 1997, 80, 317-342; d) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385-9386; e) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, 52, 5065-5075.
38. For hexakis(methano)fullerenes, see a) L. Isaacs, R. F. Haldimann, F. Diederich, Angew, Chem. 1994, 106, 2434-2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2339-2342; b) P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 1996, 79, 1047-1058; c) L. Isaacs, F. Diederich, R. F. Haldimann, Helv. Chim. Acta 1997, 80, 317-342; d) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385-9386; e) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, 52, 5065-5075.
39. For hexakis(methano)fullerenes, see a) L. Isaacs, R. F. Haldimann, F. Diederich, Angew, Chem. 1994, 106, 2434-2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2339-2342; b) P. Seiler, L. Isaacs, F. Diederich, Helv. Chim. Acta 1996, 79, 1047-1058; c) L. Isaacs, F. Diederich, R. F. Haldimann, Helv. Chim. Acta 1997, 80, 317-342; d) A. Hirsch, I. Lamparth, T. Grösser, H. R. Karfunkel, J. Am. Chem. Soc. 1994, 116, 9385-9386; e) I. Lamparth, A. Herzog, A. Hirsch, Tetrahedron 1996, 52, 5065-5075.
40. a) I. Lamparth, C. Maichle-Mössmer, A. Hirsch. Angew. Chem. 1995, 707, 1755-1757; Angew. Chem. Int. Ed. Engl. 1995, 34, 1607-1609;
41. a) I. Lamparth, C. Maichle-Mössmer, A. Hirsch. Angew. Chem. 1995, 707, 1755-1757; Angew. Chem. Int. Ed. Engl. 1995, 34, 1607-1609;
42. b) X. Camps, H. Schönberger, A. Hirsch, Chem. Eur. J. 1997, 3, 561-567;
43. c) P. Timmerman, L. E. Witschel, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1996, 79, 6-20.
44. Kα radiation using ω scans, λ = 1.54178 Å. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101 112. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
45. F. Cardullo, P. Seiler, L. Isaacs, J.-F. Nierengarten, R. F. Haldimann, F. Diederich, T. Mordasini-Denti, W. Thiel, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1997, 80, 343-371.