A polymacrocyclic oligoarylamine with a pseudobeltane motif: Towards a cylindrical multispin system

Angewandte Chemie - International Edition

Volumn 51, Issue 51, 2012, Pages 12776-12781

  Sakamaki, Daisuke ^a   Ito, Akihiro ^a   Furukawa, Ko ^b   Kato, Tatsuhisa ^a   Shiro, Motoo ^c   Tanaka, Kazuyoshi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^c RIGAKU CORPORATION   (Japan)

Author keywords

arylamines; cyclophanes; electrochemistry; ESR spectroscopy; radical ions

Indexed keywords

ARYL AMINES; CYCLOPHANES; ESR SPECTROSCOPY; MULTI-ELECTRON; RADICAL CATIONS; RADICAL IONS; REDOX ACTIVITY; RIGID COMPONENTS;

CATALYSIS; CHEMISTRY; ELECTROCHEMISTRY;

REDOX REACTIONS;

EID: 84871013600     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206831     Document Type: Article

References (84)

1. H. C. Kang, A. W. Hanson, B. Eaton, V. Boekelheide, J. Am. Chem. Soc. 1985, 107, 1979; Kohnkene
2. F. H. Kohnke, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Angew. Chem. 1987, 99, 941
3. Angew. Chem. Int. Ed. Engl. 1987, 26, 892; Collarene
4. P. R. Ashton, N. S. Isaacs, F. H. Kohnke, A. M. Z. Slawin, C. M. Spencer, J. F. Stoddart, D. J. Williams, Angew. Chem. 1988, 100, 981
5. Angew. Chem. Int. Ed. Engl. 1988, 27, 966
6. J. Benkhoff, R. Boese, F.-G. Klärner, Liebigs Ann. 1997, 501; Beltane
7. F. Vögtle, A. Schröder, D. Karbach, Angew. Chem. 1991, 103, 582
8. Angew. Chem. Int. Ed. Engl. 1991, 30, 575; Pseudobeltane
9. H. Schwierz, F. Vögtle, Synthesis 1999, 295; Belt cyclophane
10. H. Meier, K. Müller, Angew. Chem. 1995, 107, 1598
11. Angew. Chem. Int. Ed. Engl. 1995, 34, 1437; Picotube
12. S. Kammermeier, P. G. Jones, R. Herges, Angew. Chem. 1996, 108, 2834
13. Angew. Chem. Int. Ed. Engl. 1996, 35, 2669; Cyclic paraphenylacetylene
14. T. Kawase, H. R. Darabi, M. Oda, Angew. Chem. 1996, 108, 2803
15. Angew. Chem. Int. Ed. Engl. 1996, 35, 2664; [8]Cyclacene triquinone
16. R. M. Cory, C. L. McPhail, Tetrahedron Lett. 1996, 37, 1987; Vögtle belt
17. F. Vögtle, Top. Curr. Chem. 1983, 115, 157
18. G. J. Bodwell, D. O. Miller, R. J. Vermeij, Org. Lett. 2001, 3, 2093
19. 3Cyclacene
20. B. Esser, F. Rominger, R. Gleiter, J. Am. Chem. Soc. 2008, 130, 6716.
21. B. D. Steinberg, L. T. Scott, Angew. Chem. 2009, 121, 5504
22. Angew. Chem. Int. Ed. 2009, 48, 5400
23. R. Jasti, C. R. Bertozzi, Chem. Phys. Lett. 2010, 494, 1
24. T. Iwamoto, Y. Watanabe, Y. Sakamoto, T. Suzuki, S. Yamago, J. Am. Chem. Soc. 2011, 133, 8354
25. T. J. Sisto, R. Jasti, Synlett 2012, 483
26. S. Schrettl, H. Frauenrath, Angew. Chem. 2012, 124, 6673
27. Angew. Chem. Int. Ed. 2012, 51, 6569
28. U. H. F. Bunz, S. Menning, N. Martín, Angew. Chem. 2012, 124, 7202
29. Angew. Chem. Int. Ed. 2012, 51, 7094
30. H. Omachi, Y. Segawa, K. Itami, Acc. Chem. Res. 2012, 45, 1378.
31. A. Ito, Y. Ono, K. Tanaka, J. Org. Chem. 1999, 64, 8236
32. R. J. Bushby, C. A. Kilner, N. Taylor, M. E. Vale, Tetrahedron 2007, 63, 11458
33. M. Vale, M. Pink, S. Rajca, A. Rajca, J. Org. Chem. 2008, 73, 27
34. K. Ishibashi, H. Tsue, N. Sakai, S. Tokita, K. Matsui, J. Yamauchi, R. Tamura, Chem. Commun. 2008, 2812.
35. X. Z. Yan, J. Pawlas, T. Goodson III, J. F. Hartwig, J. Am. Chem. Soc. 2005, 127, 9105.
36. A. Ito, S. Inoue, Y. Hirao, K. Furukawa, T. Kato, K. Tanaka, Chem. Commun. 2008, 3242
37. A. Ito, Y. Yanagishi, K. Fukui, S. Inoue, Y. Hirao, K. Furukawa, T. Kato, K. Tanaka, Chem. Commun. 2008, 6573.
38. R. J. Bushby, D. R. McGill, K. M. Ng, N. Taylor, Chem. Commun. 1996, 2641
39. R. J. Bushby, D. R. McGill, K. M. Ng, N. Taylor, J. Chem. Soc. Perkin Trans. 2 1997, 1405. On the other hand, for macrocyclic high-spin systems containing neutral radical centers the Coulombic penalty does not apply; see, for instance: carbon-centered radicals
40. A. Rajca, S. Rajca, S. R. Desai, J. Am. Chem. Soc. 1995, 117, 806
41. K. Matsuda, N. Nakamura, K. Takahashi, K. Inoue, N. Koga, H. Iwamura, J. Am. Chem. Soc. 1995, 117, 5550; nitroxide radicals
42. A. Rajca, S. Mukherjee, M. Pink, S. Rajca, J. Am. Chem. Soc. 2006, 128, 13497
43. T. Sawai, K. Sato, T. Ise, D. Shiomi, K. Toyota, Y. Morita, T. Takui, Angew. Chem. 2008, 120, 4052
44. Angew. Chem. Int. Ed. 2008, 47, 3988
45. A. Olankitwanit, V. Kathirvelu, S. Rajca, G. R. Eaton, S. S. Eaton, A. Rajca, Chem. Commun. 2011, 47, 6443.
46. A. Ito, Y. Ono, K. Tanaka, Angew. Chem. 2000, 112, 1114
47. Angew. Chem. Int. Ed. 2000, 39, 1072
48. T. D. Selby, S. C. Blackstock, Org. Lett. 1999, 1, 2053
49. S. I. Hauck, K. V. Lakshmi, J. F. Hartwig, Org. Lett. 1999, 1, 2057
50. I. Kulszewicz-Bajer, V. Maurel, S. Gambarelli, I. Wielgus, D. Djurado, Phys. Chem. Chem. Phys. 2009, 11, 1362.
51. D. Sakamaki, A. Ito, K. Furukawa, T. Kato, K. Tanaka, Chem. Commun. 2009, 4524.
52. The present compound is structurally akin to Gleiter's π-boat cage compounds:, R. Gleiter, K. Hövermann, J. Ritter, B. Nuber, Angew. Chem. 1995, 107, 867
53. Angew. Chem. Int. Ed. Engl. 1995, 34, 789.
54. Diradicals (Ed.:, W. T. Borden,), Wiley, New York, 1982
55. H. Iwamura, Adv. Phys. Org. Chem. 1991, 26, 179
56. D. A. Dougherty, Acc. Chem. Res. 1991, 24, 88
57. A. Rajca, Chem. Rev. 1994, 94, 871
58. J. A. Crayston, J. N. Devine, J. C. Walton, Tetrahedron 2000, 56, 7829
59. K. Yoshizawa, A. Chano, A. Ito, K. Tanaka, T. Yamabe, H. Fujita, J. Yamauchi, M. Shiro, J. Am. Chem. Soc. 1992, 114, 5994
60. K. R. Stickley, S. C. Blackstock, J. Am. Chem. Soc. 1994, 116, 11576
61. K. R. Stickley, T. D. Selby, S. C. Blackstock, J. Org. Chem. 1997, 62, 448
62. M. M. Wienk, R. A. J. Janssen, J. Am. Chem. Soc. 1997, 119, 4492
63. K. Sato, M. Yano, M. Furuichi, D. Shiomi, T. Takui, K. Abe, K. Itoh, A. Higuchi, K. Katsuma, Y. Shirota, J. Am. Chem. Soc. 1997, 119, 6607, and references therein.
64. 2h symmetry were performed by using the Gaussian 09 program package: Gaussain 09 (Revision C.01), M. J. Frisch et al. Detailed geometrical information is given in the Supporting Information.
65. Ng. Ph. Buu-Hoï, J. Chem. Soc. 1952, 4346.
66. J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805
67. J. F. Hartwig, Acc. Chem. Res. 1998, 31, 852
68. J. F. Hartwig, Angew. Chem. 1998, 110, 2154
69. Angew. Chem. Int. Ed. 1998, 37, 2046
70. A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 133.
71. CCDC 879828 (1) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
72. W. Huang, T. L. E. Henderson, A. M. Bond, K. B. Oldham, Anal. Chim. Acta 1995, 304, 1.
73. A. Ishitani, S. Nagakura, Mol. Phys. 1967, 12, 1
74. B. Badger, B. Brocklehurst, R. D. Russell, Chem. Phys. Lett. 1967, 1, 122
75. A. V. Szeghalmi, M. Erdmann, V. Engel, M. Schmitt, S. Amthor, V. Kriegisch, G. Nöll, R. Stahl, C. Lambert, D. Leusser, D. Stalke, M. Zabel, J. Popp, J. Am. Chem. Soc. 2004, 126, 7834
76. Y. Hirao, A. Ito, K. Tanaka, J. Phys. Chem. A 2007, 111, 2951
77. A. Ito, D. Sakamaki, Y. Ichikawa, K. Tanaka, Chem. Mater. 2011, 23, 841.
78. F. A. Bell, A. Ledwith, D. C. Sherrington, J. Chem. Soc. 1969, 2719
79. N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877.
80. J. Heinzer, Mol. Phys. 1971, 22, 167
81. Quantum Chemistry Program Exchange 1972, No. 209. We thank Prof. S. F. Nelsen for a copy of this program (modified by P. A. Petillo, R. F. Ismagilov, and Y. Hirao).
82. J. Isoya, H. Kanda, J. R. Norris, J. Tang, M. K. Brown, Phys. Rev. B 1990, 41, 3905
83. A. V. Astashkin, A. Schweiger, Chem. Phys. Lett. 1990, 174, 595.
84. 4+ which shows a satisfactory elemental analysis, probably due to partial decomposition.