A chiral dicationic [8]circulenoid: Photochemical origin and facile thermal conversion into a helicene congener

Angewandte Chemie - International Edition

Volumn 51, Issue 48, 2012, Pages 11972-11976

  Severa, Lukáš ^a   Ončák, Milan ^c   Koval, Dušan ^a   Pohl, Radek ^a   Šaman, David ^a   Císařová, Ivana ^b   Reyes Gutiérrez, Paul E ^a   Sázelová, Petra ^a   Kašička, Václav ^a   Teplý, Filip ^a   Slavíček, Petr ^c  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

^c INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

capillary electrophoresis; cationic circulenes; closed helicenoids; isomerization; photochemistry

Indexed keywords

CHROMATOGRAPHIC PURIFICATION; CIRCULENES; CLOSED HELICENOIDS; HELICENES; PHOTOCYCLOADDITION; THERMAL CONVERSION;

CAPILLARY ELECTROPHORESIS; ISOMERIZATION; PHOTOCHEMICAL REACTIONS;

CHROMATOGRAPHIC ANALYSIS;

EID: 84870048979     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203562     Document Type: Article

References (89)

1. J. H. Dopper, H. Wynberg, Tetrahedron Lett. 1972, 13, 763
2. H. Christoph, J. Grunenberg, H. Hopf, I. Dix, P. G. Jones, M. Scholtissek, G. Maier, Chem. Eur. J. 2008, 14, 5604.
3. W. E. Barth, R. G. Lawton, J. Am. Chem. Soc. 1966, 88, 380; for a review, see
4. Y.-T. Wu, J. S. Siegel, Chem. Rev. 2006, 106, 4843.
5. K. Yamamoto, T. Harada, M. Nakazaki, T. Nakao, Y. Kai, S. Harada, N. Kasai, J. Am. Chem. Soc. 1983, 105, 7171
6. K. Yamamoto, Pure Appl. Chem. 1993, 65, 157
7. K. Yamamoto, H. Sonobe, H. Matsubara, M. Sato, S. Okamoto, K. Kitaura, Angew. Chem. 1996, 108, 69
8. Angew. Chem. Int. Ed. Engl. 1996, 35, 69.
9. H. Hopf, Classics in Hydrocarbon Chemistry, Wiley-VCH, Weinheim, 2000, p. 330
10. J. S. Siegel, T. J. Seiders, Chem. Br. 1995, 31, 313.
11. For heterocyclic circulenes of interest for materials chemistry, see:, K. Y. Chernichenko, V. V. Sumerin, R. V. Shpanchenko, E. S. Balenkova, V. G. Nenajdenko, Angew. Chem. 2006, 118, 7527
12. Angew. Chem. Int. Ed. 2006, 45, 7367; for seminal reports, see: Ref. [1a] and
13. J. H. Dopper, H. Wynberg, J. Org. Chem. 1975, 40, 1957.
14. L. T. Scott, M. M. Hashemi, M. S. Bratcher, J. Am. Chem. Soc. 1992, 114, 1920
15. A. Borchardt, A. Fuchicello, K. V. Kilway, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1992, 114, 1921
16. T. J. Seiders, K. K. Baldridge, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 2001, 123, 517
17. D. Eisenberg, A. S. Filatov, E. A. Jackson, M. Rabinovitz, M. A. Petrukhina, L. T. Scott, R. Shenhar, J. Org. Chem. 2008, 73, 6073; for the dynamics of [7]circulene, see
18. M. Shen, I. S. Ignatyev, Y. Xie, H. F. Schaefer III, J. Phys. Chem. 1993, 97, 3212.
19. S. Iijima, T. Ichihashi, Y. Ando, Nature 1992, 356, 776
20. J.-C. Charlier, Acc. Chem. Res. 2002, 35, 1063
21. Y.-Z. Tan, et al., Nat. Commun. 2011, 2, 420
22. Bharat, R. Bhola, T. Bally, A. Valente, M. K. Cyrański, Ś. Dobrzycki, S. M. Spain, P. Rempała, M. R. Chin, B. T. King, Angew. Chem. 2010, 122, 409
23. Angew. Chem. Int. Ed. 2010, 49, 399, and references therein
24. A. Sygula, P. W. Rabideau, in Carbon-Rich Compounds: From Molecules to Materials (Eds.:, M. M. Haley, R. R. Tykwinski,), Wiley-VCH, Weinheim, 2006, p. 529
25. X. Lu, Z. Chen, Chem. Rev. 2005, 105, 3643
26. V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106, 4868
27. B. D. Steinberg, L. T. Scott, Angew. Chem. 2009, 121, 5504
28. Angew. Chem. Int. Ed. 2009, 48, 5400.
29. R. Salcedo, L. E. Sansores, A. Picazo, L. Sansõn, J. Mol. Struct. (Theochem) 2004, 678, 211
30. T. N. Gribanova, N. S. Zefirov, V. I. Minkin, Pure Appl. Chem. 2010, 82, 1011.
31. For selected reviews on helicenes, see:, Y. Shen, C.-F. Chen, Chem. Rev. 2012, 112, 1463
32. A. Rajca, M. Miyasaka, in Functional Organic Materials (Eds.:, T. J. J. Müller, U. H. F. Bunz,), Wiley-VCH, Weinheim, 2007, p. 543
33. A. Urbano, Angew. Chem. 2003, 115, 4116
34. Angew. Chem. Int. Ed. 2003, 42, 3986
35. T. J. Katz, Angew. Chem. 2000, 112, 1997
36. Angew. Chem. Int. Ed. 2000, 39, 1921; Ref. [4a], p. 323.
37. The term closed helicene has been also used as an alternative for circulene (see Ref. [3b]); for a discussion of Wynberg's dehydrohelicenes and a definition of quasi-[m]circulenes, see:, A. Rajca, M. Miyasaka, S. Xiao, P. J. Boratyn'ski, M. Pink, S. Rajca, J. Org. Chem. 2009, 74, 9105.
38. L. Adriaenssens, L. Severa, T. Šálová, I. Císařová, R. Pohl, D. Šaman, S. V. Rocha, N. S. Finney, L. Pospíšil, P. Slavíček, F. Teplý, Chem. Eur. J. 2009, 15, 1072
39. L. Severa, L. Adriaenssens, J. Vávra, D. Šaman, I. Císařová, P. Fiedler, F. Teplý, Tetrahedron 2010, 66, 3537
40. L. Severa, D. Koval, P. Novotná, M. Ončák, P. Sázelová, D. Šaman, P. Slavíček, M. Urbanová, V. Kašička, F. Teplý, New J. Chem. 2010, 34, 1063
41. J. Vávra, L. Severa, P. Švec, I. Císař ová, D. Koval, P. Sázelová, V. Kašička, F. Teplý, Eur. J. Org. Chem. 2012, 489
42. L. Pospíšil, F. Teplý, M. Gál, L. Adriaenssens, M. Horáček, L. Severa, Phys. Chem. Chem. Phys. 2010, 12, 1550.
43. L. Adriaenssens, L. Severa, D. Koval, I. Císařová, M. Martínez Belmonte, E. C. Escudero-Adán, P. Novotná, P. Sázelová, J. Vávra, R. Pohl, D. Šaman, M. Urbanová, V. Kašička, F. Teplý, Chem. Sci. 2011, 2, 2314; for related study on [5]helquat, see
44. L. Severa, M. Jirásek, P. Švec, F. Teplý, Á. Révész, D. Schröder, D. Koval, V. Kašička, I. Císařová, D. Šaman, ChemPlusChem 2012, 77, 624.
45. I. G. Stará, I. Starý, A. Kollárovič, F. Teplý, D. Šaman, M. Tichý, J. Org. Chem. 1998, 63, 4046; for further reports, see
46. P. Sehnal, I. G. Stará, D. Šaman, M. Tichý, J. Míšek, J. Cvačka, L. Rulíšek, J. Chocholoušová, J. Vacek, G. Goryl, M. Szymonski, I. Císařová, I. Starý, Proc. Natl. Acad. Sci. USA 2009, 106, 13169
47. J. Míšek, F. Teplý, I. G. Stará, M. Tichý, D. Šaman, I. Císařová, P. Vojtíšek, I. Starý, Angew. Chem. 2008, 120, 3232
48. Angew. Chem. Int. Ed. 2008, 47, 3188.
49. for Siegel's indenocorrannulenes, see:, Y.-T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870
50. for Wender's substituted cyclooctatetraenes, see:, P. A. Wender, J. P. Christy, A. B. Lesser, M. T. Gieseler, Angew. Chem. 2009, 121, 7823
51. Angew. Chem. Int. Ed. 2009, 48, 7687
52. Shibata's tetraphenylenes:, T. Shibata, T. Chiba, H. Hirashima, Y. Ueno, K. Endo, Angew. Chem. 2009, 121, 8210
53. Angew. Chem. Int. Ed. 2009, 48, 8066.
54. CCDC 854998 (rac- 1), 854997 (rac- 2), and 854996 (rac- 3) contain 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.
55. D. Koval, L. Severa, L. Adriaenssens, J. Vávra, F. Teplý, V. Kašička, Electrophoresis 2011, 32, 2683.
56. T. Bach, J. P. Hehn, Angew. Chem. 2011, 123, 1032
57. Angew. Chem. Int. Ed. 2011, 50, 1000
58. N. Hoffmann, Chem. Rev. 2008, 108, 1052
59. P. Klán, J. Wirz, Photochemistry of Organic Compounds: From Concepts to Practice, Wiley, Chichester, 2009.
60. W. J. Schreier, T. E. Schrader, F. O. Koller, P. Gilch, C. E. Crespo-Hernández, V. N. Swaminathan, T. Carell, W. Zinth, B. Kohler, Science 2007, 315, 625, and references therein.
61. T. Shinmyozu, R. Nogita, M. Akita, C. Lim, in CRC Handbook of Organic Photochemistry and Photobiology, 2 nd ed., (Eds.: W. Horspool, F. Lenci,), CRC, Boca Raton, 2004, pp. 22 /1- 22 /21 and 23/1-23/11.
62. H. Prinzbach, G. Sedelmeier, C. Krüger, R. Goddard, H.-D. Martin, R. Gleiter, Angew. Chem. 1978, 90, 297
63. Angew. Chem. Int. Ed. Engl. 1978, 17, 271
64. W.-D. Fessner, G. Sedelmeier, P. R. Spurr, G. Rihs, H. Prinzbach, J. Am. Chem. Soc. 1987, 109, 4626.
65. H. Higuchi, K. Takatsu, T. Otsubo, Y. Sakata, S. Misumi, Tetrahedron Lett. 1982, 23, 671
66. H. Higuchi, E. Kobayashi, Y. Sakata, S. Misumi, Tetrahedron 1986, 42, 1731
67. S. Misumi, Pure Appl. Chem. 1987, 59, 1627.
68. Wasserman's dibenzoequinene:, H. H. Wasserman, P. M. Keehn, J. Am. Chem. Soc. 1967, 89, 2770
69. H.-D. Becker, Chem. Rev. 1993, 93, 145
70. Nishimura's naphtalenophane:, J. Nishimura, M. Takeuchi, H. Takahashi, M. Sato, Tetrahedron Lett. 1990, 31, 2911; for Shinmyozu's efforts towards hexaprismane, see
71. C. Lim, M. Yasutake, T. Shinmyozu, Angew. Chem. 2000, 112, 593
72. Angew. Chem. Int. Ed. 2000, 39, 578
73. R. Nogita, K. Matohara, M. Yamaji, T. Oda, Y. Sakamoto, T. Kumagai, C. Lim, M. Yasutake, T. Shimo, C. W. Jefford, T. Shinmyozu, J. Am. Chem. Soc. 2004, 126, 13732
74. Okamoto's octahedrane:, H. Okamoto, K. Satake, H. Ishida, M. Kimura, J. Am. Chem. Soc. 2006, 128, 16508.
75. H. Ihmels, J. Luo, J. Photochem. Photobiol. A 2008, 200, 3
76. D. Q. Wu, L. J. Zhi, G. J. Bodwell, G. L. Cui, N. Tsao, K. Müllen, Angew. Chem. 2007, 119, 5513
77. Angew. Chem. Int. Ed. 2007, 46, 5417
78. S. Arai, T. Yafune, M. Ohkubo, M. Hida, Tetrahedron Lett. 1989, 30, 7217.
79. For a recent [2+2] photocycloaddition of a helicene to form a dimer, see:, K. Yavari, S. Moussa, B. Ben Hassine, P. Retailleau, A. Voituriez, A. Marinetti, Angew. Chem. 2012, 124, 6852
80. Angew. Chem. Int. Ed. 2012, 51, 6748.
81. E. Schaumann, R. Ketcham, Angew. Chem. 1982, 94, 231
82. Angew. Chem. Int. Ed. Engl. 1982, 21, 225.
83. S. Grimme, J. Comput. Chem. 2006, 27, 1787.
84. Gaussian 09, Revision A.1, M. J. Frisch et al., Gaussian, Inc., Wallingford CT, 2009.
85. C. Doubleday, Jr., R. N. Camp, H. F. King, J. W. McIver, Jr., D. Mullally, M. Page, J. Am. Chem. Soc. 1984, 106, 447
86. J. Liese, N. Hampp, J. Phys. Chem. A 2011, 115, 2927
87. R. Hoffmann, S. Swaminathan, B. G. Odell, R. Gleiter, J. Am. Chem. Soc. 1970, 92, 7091.
88. A. D. Boese, J. M. L. Martin, J. Chem. Phys. 2004, 121, 3405.
89. M. Flammang-Barbieux, J. Nasielski, R. H. Martin, Tetrahedron Lett. 1967, 8, 743.