The tetraaza[1.1.1.1]m,p,m,p-cyclophane dication: A triplet diratical having two m-phenylenediamine radical cations linked by twisted benzenes

Angewandte Chemie - International Edition

Volumn 39, Issue 6, 2000, Pages 1072-1075

  Ito, Akihiro ^a   Ono, Yukiharu ^a   Tanaka, Kazuyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cyclophanes; Density functional calculations; Diradicals; EPR spectroscopy; Polycations

Indexed keywords

BENZENE DERIVATIVE; CYCLOPHANE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034678007     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1072::AID-ANIE1072>3.0.CO;2-1     Document Type: Article

References (68)

1. a) F. Diederich, Cyclophanes, The Royal Society of Chemistry, Cambridge, UK, 1991;
2. b) F. Vögtle, Cyclophane Chemistry, Wiley, Chichester, 1993.
3. B. Morgan, D. Dolphin in Structure and Bonding, Vol. 64 (Ed.: J. W. Buchler), Springer, Berlin, 1987, p. 115.
4. a) C. D. Gutsche, Calixarenes, The Royal Society of Chemistry, Cambridge, UK, 1989;
5. b) R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. I., Bluening, B. J. Tarbet, Chem. Rev. 1992, 92, 1261;
6. c) S. Shinkai, Tetrahedron 1993, 49, 8933;
7. d) V. Böhmer, Angew. Chem. 1995, 107, 785; Angew. Chem. Int. Ed. Engl. 1995, 34, 713;
8. d) V. Böhmer, Angew. Chem. 1995, 107, 785; Angew. Chem. Int. Ed. Engl. 1995, 34, 713;
9. e) A. Ikeda, S. Shinkai, Chem. Rev. 1997, 97, 1713.
10. a) B. König, M. Rödel, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 107, 752; Angew. Chem. Int. Ed. Engl. 1995, 34, 661;
11. a) B. König, M. Rödel, P. Bubenitschek, P. G. Jones, Angew. Chem. 1995, 107, 752; Angew. Chem. Int. Ed. Engl. 1995, 34, 661;
12. b) B. König, M. Rödel, P. Bubenitschek, P. G. Jones, I. Thondorf, J. Org. Chem. 1995, 60, 7406;
13. c) M. Mascal, J. L. Richardson, A. J. Blake, W.-S. Li, Tetrahedron Lett. 1997, 38, 7639;
14. d) J. Nakayama, N. Katano, Y. Sugihara, A. Ishii, Chem. Lett. 1997, 897;
15. e) N. Katano, Y. Sugihara, A. Ishii, J. Nakayama, Bull. Chem. Soc. Jpn. 1998, 71, 2695, and references therein;
16. f) N. Avarvari, N. Mézailles, L. Ricard, P. Le Floch, F. Mathey, Science 1998, 280, 1587;
17. g) A. S. Abd-El-Aziz, C. R. de Denus, M. J. Zaworotko, C. V. K. Sharma, Chem. Commun. 1998, 265;
18. h) I. Baxter, H. M. Colquhoun, P. Hodge, F. H. Kohnke, D. J. Williams, Chem. Commun. 1998, 283;
19. i) I. Baxter, H. M. Colquhoun, P. Hodge, F. H. Kohnke, D. J. Williams, Chem. Commun. 1998, 1991;
20. j) T. Fruend, C. Kübel, M. Baumgarten, V. Enkelmann, L. Gherghel, R. Reuter, K. Müllen, Eur. J. Org. Chem. 1998, 555;
21. k) M. Yoshida, M. Goto, F. Nakanishi, Organometallics 1999, 18, 1465;
22. l) N. Avarvari, N. Maigrot, L. Ricard, F. Mathey, P. Le Floch, Chem. Eur. J. 1999, 5, 2109.
23. a) A. Ito, Y. Ono, K. Tanaka, New J. Chem. 1998, 779;
24. b) A. Ito, Y. Ono, K. Tanaka, J. Org. Chem. 1999, 64, 8236.
25. a) A. Rajca, S. Rajca, R. Padmakumar, Angew. Chem. 1994, 106, 2193; Angew. Chem. Int. Ed. Engl. 1994, 33, 2091;
26. a) A. Rajca, S. Rajca, R. Padmakumar, Angew. Chem. 1994, 106, 2193; Angew. Chem. Int. Ed. Engl. 1994, 33, 2091;
27. b) A. Rajca, S. Rajca, S. R. Desai, J. Am. Chem. Soc. 1995, 117, 806;
28. c) K. Matsuda, N. Nakamura, K. Takahashi, K. Inoue, N. Koga, H. Iwamura, J. Am. Chem. Soc. 1995, 117, 5550;
29. d) A. Rajca, K. Lu, S. Rajca, J. Am. Chem. Soc. 1997, 119, 10335;
30. e) A. Rajca, J. Wongsriratanakul, S. Rajca, J. Am. Chem. Soc. 1997, 119, 11674;
31. f) A. Rajca, J. Wongsriratanakul, S. Rajca, R. Cerny, Angew. Chem. 1998, 110, 1353; Angew. Chem. Int. Ed. 1998, 37, 1229;
32. f) A. Rajca, J. Wongsriratanakul, S. Rajca, R. Cerny, Angew. Chem. 1998, 110, 1353; Angew. Chem. Int. Ed. 1998, 37, 1229;
33. g) A. Rajca, S. Rajca, J. Wongsriratanakul, J. Am. Chem. Soc. 1999, 121, 6308.
34. A. R. Forrester, J. M. Hay, R. H. Thomson, Organic Chemistry of Stable Free Radicals, Academic Press, New York, 1968.
35. a) H. Iwamura, Pure Appl. Chem. 1987, 59, 1595;
36. b) H. Iwamura, Adv. Phys. Org. Chem. 1990, 26, 179;
37. c) D. A. Dougherty, Acc. Chem. Res. 1991, 24, 88;
38. d) H. Iwamura, Pure Appl. Chem. 1993, 65, 57;
39. e) W. T. Borden, H. Iwamura, J. A. Berson, Acc. Chem. Res. 1994, 24, 109;
40. f) A. Rajca, Chem. Rev. 1994, 94, 871.
41. a) M. M. Wienk, R. A. J. Janssen, Chem. Commun. 1996, 267;
42. b) M. M. Wienk, R. A. J. Janssen, J. Am. Chem. Soc. 1996, 118, 10626;
43. c) M. M. Wienk, R. A. J. Janssen, J. Am. Chem. Soc. 1997, 119, 4492;
44. d) K. R. Stickley, T. D. Selby, S. C. Blackstock, J. Org. Chem. 1997, 62, 448;
45. e) T. D. Selby, S. C. Blackstock, J. Am. Chem. Soc. 1999, 121, 7152.
46. A. Ito, A. Taniguchi, T. Yamabe, K. Tanaka, Org. Lett. 1999, 1, 741.
47. Treatment at a moderate dilution (10-50 mM) remedies the yield of 1 (ca. 1%). On the other hand, prolonged reaction time does not improve the yield.
48. max (lgε) - 265 (4.3), 325 nm (3.5).
49. 2- were calculated using the split-valence 6-31G* basis set on the basis of density functional theory (DFT), which incorporates dynamical correlation, giving reliable results. We employed Becke's nonlocal exchange functional (A. D. Becke, Phys. Rev. A 1988, 38, 3098), and Perdew and Wang's gradient-corrected correlation functional (J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 45, 13244); BPW91/6-31G* was applied using the GAUSSIAN94 suite of programs (M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94, Revision D.4; Gaussian, Inc., Pittsburg, PA, 1995).
50. 2- were calculated using the split-valence 6-31G* basis set on the basis of density functional theory (DFT), which incorporates dynamical correlation, giving reliable results. We employed Becke's nonlocal exchange functional (A. D. Becke, Phys. Rev. A 1988, 38, 3098), and Perdew and Wang's gradient-corrected correlation functional (J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 45, 13244); BPW91/6-31G* was applied using the GAUSSIAN94 suite of programs (M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94, Revision D.4; Gaussian, Inc., Pittsburg, PA, 1995).
51. 2- were calculated using the split-valence 6-31G* basis set on the basis of density functional theory (DFT), which incorporates dynamical correlation, giving reliable results. We employed Becke's nonlocal exchange functional (A. D. Becke, Phys. Rev. A 1988, 38, 3098), and Perdew and Wang's gradient-corrected correlation functional (J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 45, 13244); BPW91/6-31G* was applied using the GAUSSIAN94 suite of programs (M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian 94, Revision D.4; Gaussian, Inc., Pittsburg, PA, 1995).
52. -1).
53. T. Moll, J. Heinze, Synth. Met. 1993, 55-57, 1521.
54. F. A. Bell, A. Ledwith, D. C. Sherrington, J. Chem. Soc. 1969, 2720.
55. 18]
56. 18]
57. a) A. Calder, A. R. Forrester, P. G. James, G. R. Luckhurst, J. Am. Chem. Soc. 1969, 91, 3724;
58. b) J. F. W. Keana, R. J. Dinerstein, J. Am. Chem. Soc. 1971, 93, 2808;
59. c) A. Rassat, H. U. Sieveking, Angew. Chem. 1972, 84, 353; Angew. Chem. Int. Ed. Engl. 1972, 11, 303;
60. c) A. Rassat, H. U. Sieveking, Angew. Chem. 1972, 84, 353; Angew. Chem. Int. Ed. Engl. 1972, 11, 303;
61. d) R.-M. Dupeyre, A. Rassat, J. Ronzaud, J. Am. Chem. Soc. 1974, 96, 6559;
62. e) P. Michon, A. Rassat, J. Am. Chem. Soc. 1975, 97, 696;
63. f) W. B. Gleason, R. E. Barnett, J. Am. Chem. Soc. 1976, 98, 2701;
64. g) M. Dvolaitzky, R. Chiarelli, A. Rassat, Angew. Chem. 1992, 104, 220; Angew. Chem. Int. Ed. Engl. 1992, 31, 180.
65. g) M. Dvolaitzky, R. Chiarelli, A. Rassat, Angew. Chem. 1992, 104, 220; Angew. Chem. Int. Ed. Engl. 1992, 31, 180.
66. 2-.
67. A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456; Angew. Chem. Int. Ed. Engl. 1995, 34, 1348.
68. A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456; Angew. Chem. Int. Ed. Engl. 1995, 34, 1348.