A synthetic approach towards interlocked π-conjugated macrocycles

European Journal of Organic Chemistry

Volumn , Issue 8, 2006, Pages 1940-1948

  Ammann, Martin ^a,c   Rang, Alexander ^b   Schalley, Christoph A ^b,d   Bäuerle, Peter ^a  

^a UNIVERSITY OF ULM   (Germany)

^b UNIVERSITY OF BONN   (Germany)

^c NOVALED GmbH   (Germany)

^d FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Catenates; Conjugated interlocked macrocycle; Macrocycles; Mass spectrometry; Oligothiophene; Phenanthroline

Indexed keywords

EID: 33646190364     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200500938     Document Type: Article

References (75)

1. P. Bäuerle, "Oligothiophenes" in Electronic Materials: The Oligomeric Approach, (Eds.: K. Müllen, G. Wegner), Wiley-VCH, Weinheim, 1998.
2. a) J. Krömer, I. Rios-Carreras, G. Fuhrmann, C. Musch, M. Wunderlin, T. Debaerdemaeker, E. Mena-Osteritz, P. Bäuerle, Angew. Chem. Int. Ed. 2000, 39, 3481-3486;
3. b) G. Fuhrmann, J. Krömer, P. Bäuerle, Synth. Met. 2001, 119, 125-126;
4. c) G. Fuhrmann, T. Debaerdemaeker, P. Bäuerle, Chem. Commun. 2003, 948-949.
5. M. Bednarz, P. Reineker, E. Mena-Osteritz, P. Bäuerle, J. Lumin. 2004, 110, 225-231.
6. a) E. Mena-Osteritz, P. Bäuerle, Adv. Mater. 2001, 13, 243-246;
7. b) E. Mena-Osteritz, Adv. Mater. 2002, 14, 609-616.
8. E. Mena-Osteritz, P. Bäuerle, Adv. Mater., in press; DOI: 10.1002/adma.200501575.
9. a) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 2000, 39, 3348-3391;
10. b) A. R. Pease, J. O. Jeppesen, J. F. Stoddart, Y. Luo, C. P. Collier, J. R. Heath, Acc. Chem. Res. 2001, 34, 433-444;
11. c) Y. Luo, C. P. Collier, J. O. Jeppesen, K. A. Nielsen, E. Delonno, G. Ho, J. Perkins, H.-R. Tseng, T. Yamamoto, J. F. Stoddart, J. R. Heath, ChemPhysChem 2002, 3, 519-525;
12. d) C. A. Schalley, K. Beizai, F. Vögtle, Acc. Chem. Res. 2001, 34, 465-476;
13. e) V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines, Wiley-VCH, Weinheim, 2003;
14. f) C. A. Schalley, A. Lützen, M. Albrecht, Chem. Eur. J. 2004, 10, 1072-1080.
15. For general reviews on template effects, see: a) D. H. Busch, N. A. Stephensen, Coord. Chem. Rev. 1990, 100, 119-154;
16. b) R. Cacciapaglia, L. Mandolini, Chem. Soc. Rev. 1993, 22, 221-231;
17. c) S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475;
18. d) N. V. Gerbeleu, V. B. Arion, J. Burgess, Template Synthesis of Macrocyclic Compounds, Wiley-VCH, Weinheim, 1999;
19. e) F. Diederich, P. J. Stang (Eds.), Templated Organic Synthesis, Wiley-VCH, Weinheim, 2000;
20. f) T. J. Hubin, D. H. Busch, Coord. Chem. Rev. 2000, 200, 5-52.
21. a) C. O. Dietrich-Buchecker, J.-P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095-5098;
22. b) C. O. Dietrich-Buchecker, J.-P. Sauvage, Chem. Rev. 1987, 87, 795-810;
23. c) J.-P. Sauvage, Acc. Chem. Res. 1990, 23, 319-327;
24. for a book on mechanically interlocked molecules, see: d) J.-P. Sauvage, C. O. Dietrich-Buchecker (Eds.), Molecular Catenanes, Rotaxanes, and Knots, Wiley-VCH, Weinheim, 1999.
25. a) D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828;
26. b) D. Philp, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196;
27. c) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976;
28. d) F. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1043-1063.
29. a) C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311;
30. b) H. Adams, F. J. Carver, C. A. Hunter, J. Chem. Soc., Chem. Commun. 1995, 809-810.
31. a) A. G. Johnston, D. A. Leigh, L. Nezhat, J. P. Smart, M. D. Deegan, Angew. Chem. Int. Ed. Engl. 1995, 34, 1212-1216;
32. b) D. A. Leigh, K. Moody, J. P. Smart, K. J. Watson, A. M. Z. Slawin, Angew. Chem. Int. Ed. Engl. 1996, 35, 306-310.
33. a) F. Vögtle, S. Meier, R. Hoss, Angew. Chem. Int. Ed. Engl. 1992, 31, 1619-1622;
34. b) R. Hoss, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384;
35. c) F. Vögtle, T. Dünnwald, T. Schmidt, Acc. Chem. Res. 1996, 29, 451-460;
36. d) R. Jäger, F. Vögtle, Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944;
37. e) G. M. Hübner, J. Gläser, C. Seel, F. Vögtle, Angew. Chem. Int. Ed. 1999, 38, 383-386;
38. f) C. Reuter, F. Vögtle, Org. Lett. 2000, 2, 593-595;
39. g) C. A. Schalley, G. Silva, C. F. Nising, P. Linnartz, Helv. Chim. Acta 2002, 85, 1578-1596;
40. h) P. Ghosh, O. Mermagen, C. A. Schalley, Chem. Commun. 2002, 2628-2629;
41. for a review, see: i) M. Kogej, P. Ghosh, C. A. Schalley, "How to thread a string into the eye of a molecular needle: Template-directed synthesis of mechanically interlocked molecules" in Strategies and Tactics in Organic Synthesis (Ed.: M. Harmata), Elsevier, Amsterdam, 2004, vol. 4, pp. 171-210.
42. a) M. Fujita, Acc. Chem. Res. 1999, 32, 53-61;
43. b) K. Biradha, M. Fujita, Adv. Supramol. Chem. 2000, 6, 1-39;
44. c) A. Hori, K. Kumazawa, T. Kusukawa, D. K. Chand, M. Fujita, S. Sakamoto, K. Yamaguchi, Chem. Eur. J. 2001, 7, 4142-4149.
45. a) C. P. McArdle, M. J. Irwin, M. C. Jennings, R. J. Puddephatt, Angew. Chem. Int. Ed. 1999, 38, 3376-3378;
46. b) C. P. McArdle, M. C. Jennings, J. J. Vittal, R. J. Puddephatt, Chem. Eur. J. 2001, 7, 3572-3583.
47. a) K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308-1312;
48. b) S. J. Cantrill, K. S. Chichak, A. J. Peters, J. F. Stoddart, Acc. Chem. Res. 2005, 38, 1-9.
49. a) T. Felder, C. A. Schalley, Angew. Chem. Int. Ed. 2003, 42, 2258-2260;
50. b) P. Linnartz, S. Bitter, C. A. Schalley, Eur. J. Org. Chem. 2003, 4819-4829;
51. c) P. Linnartz, C. A. Schalley, Supramol. Chem. 2004, 16, 263-267.
52. a) M. Przybylski, M. O. Glocker, Angew. Chem. Int. Ed. Engl. 1996, 35, 806-826;
53. b) J. S. Brodbelt, Int. J. Mass Spectrom. 2000, 200, 57-69;
54. c) C. A. Schalley, Int. J. Mass Spectrom. 2000, 194, 11-39;
55. d) C. B. Lebrilla, Acc. Chem. Res. 2001, 34, 653-661;
56. e) C. A. Schalley, Mass Spectrom. Rev. 2001, 20, 253-309.
57. For an example of a supramolecular neighboring group effect in the fragmentation of metallosupramolecular squares, see: C. A. Schalley, T. Müller, P. Linnartz, M. Witt, M. Schäfer, A. Lützen, Chem. Eur. J. 2002, 8, 3538-3551.
58. a) C. A. Schalley, R. K. Castellano, M. S. Brody, D. M. Rudkevich, G. Siuzdak, J. Rebek Jr, J. Am. Chem. Soc. 1999, 121, 4568-4579;
59. b) C. A. Schalley, T. Martín, U. Obst, J. Rebek Jr, J. Am. Chem. Soc. 1999, 121, 2133-2138;
60. c) B. M. O'Leary, T. Szabo, N. Svenstrup, C. A. Schalley, A. Lützen, J. Rebek Jr, J. Am. Chem. Soc. 2001, 123, 11519-11533;
61. d) H. Mansikkamäki, M. Nissinen, C. A. Schalley, New J. Chem. 2003, 27, 88-97;
62. e) R. Zadmard, M. Junkers, T. Schrader, T. Grawe, A. Kraft, J. Org. Chem. 2003, 68, 6511-6521;
63. f) R. Zadmard, T. Schrader, U. Linne, Chem. Eur. J. 2004, 10, 4233-4239;
64. g) I. Müller, D. Möller, C. A. Schalley, Angew. Chem. Int. Ed. 2005, 44, 480-484.
65. a) C. A. Schalley, J. Hoernschemeyer, X.-Y. Li, G. Silva, P. Weis, Int. J. Mass Spectrom. 2003, 228, 373-388;
66. b) C. A. Schalley, P. Ghosh, M. Engeser, Int. J. Mass Spectrom. 2004, 232-233, 249-258.
67. M. Ammann, P. Bäuerle, Org. Biomol. Chem. 2005, 3, 4143-4152.
68. a) P.-L. Vidal, B. Divisia-Blohorn, G. Bidan, Inorg. Chem. 1999, 38, 4203-4210;
69. b) P.-L. Vidal, B. Divisia-Blohorn, G. Bidan, J.-L. Hazemann, J.-M. Kern, J.-P. Sauvage, Chem. Eur. J. 2000, 6, 1663-1673;
70. c) J.-P. Sauvage, J.-M. Kern, G. Bidan, B. Divisia-Blohorn, P.-L. Vidal, New J. Chem. 2002, 26, 1287-1290.
71. a) R. Rossi, A. Carpita, C. Bigelli, Tetrahedron Lett. 1985, 26, 523-526;
72. b) N. G. Kundu, M. Pal, C. Chowdhury, J. Chem. Res. (S) 1993, 432-433.
73. C. O. Dietrich-Buchecker, A. Edel, J. P. Kitzinger, J.-P. Sauvage, Tetrahedron 1987, 43, 333-344.
74. T. G. Appleton, M. A. Bennett, I. B. Tomkins, J. Chem. Soc., Dalton Trans. 1976, 439-446.
75. C. O. Dietrich-Buchecker, J.-P. Sauvage, J.-M. Kern, J. Am. Chem. Soc. 1989, 111, 7791-7800.