Cyclic [5]paraphenyleneacetylene: Synthesis, properties, and formation of a ring-in-ring complex showing a considerably large association constant and entropy effect

Angewandte Chemie - International Edition

Volumn 46, Issue 7, 2007, Pages 1086-1088

  Kawase, Takeshi ^a   Nishiyama, Yoshitaka ^a   Nakamura, Takamitsu ^a   Ebi, Takahiro ^a   Matsumoto, Kouzou ^a   Kurata, Hiroyuki ^a   Oda, Masaji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Cyclic alkynes; Host guest systems; Inclusion compounds; Noncovalent interactions; Strained molecules

Indexed keywords

AROMATIC COMPOUNDS; ASSOCIATION REACTIONS; ELECTROSTATICS; ENTROPY; INCLUSIONS; SYNTHESIS (CHEMICAL);

CYCLIC ALKYNES; ENTROPY EFFECT; INCLUSION COMPOUNDS; NONCOVALENT INTERACTIONS;

UNSATURATED COMPOUNDS;

EID: 34250760417     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603707     Document Type: Article

References (67)

1. a) H. W. Kroto, K. G. Mckay, Nature 1988, 331, 328-331;
2. b) S. Iijima, J. Cryst. Growth 1989, 50, 675-683;
3. c) D. Ugarte, Nature 1992, 359, 707-709.
4. a) S. Iijima, Nature 1991, 354, 56-58;
5. b) B. W. Smith, M. Monthioux, D. E. Luzzi, Nature 1998 396, 323-325.
6. a) B. W. Smith, M. Monthioux, D. E. Luzzi, Nature 1998, 396, 323-324;
7. b) J. Sloan, A. I. Kirkland, J. L. Hutchison, M. L. H. Green, Chem. Commun. 2002, 1319-1332.
8. a) R. C. Haddon, Science 1993, 261, 1545-1550;
9. b) M. Kamieth, F.-G. Klärner, F. Diederich, Angew. Chem. 1998, 110, 3497-3500;
10. Angew. Chem. Int. Ed. 1998, 37, 3303-3306;
11. c) L. T. Scott, Pure Appl. Chem. 1999, 71, 209-219;
12. d) K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 5332-5333;
13. e) R. B. Ansems, L. T. Scott, J. Phys. Org. Chem. 2004, 17, 819-823;
14. f) U. D. Priyakumar, M. Punnagai, G. P. Krishna Mohan, G. N. Sastry, Tetrahedron 2004, 60, 3037-3043;
15. g) Y.-T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870-6884.
16. a) R. Saito, G. Dresselhaus, M. S. Dresselhaus, J. Appl. Phys. 1993, 73(2), 494-500;
17. b) J. Cumings, A. Zettl, Science 2000, 289, 602-604;
18. c) A. N. Khlobystov, D. A. Britz, G. A. D. Briggs, Acc. Chem. Res. 2005, 38, 901-909.
19. J. Lu, S. Nagase, X. Zhang, D. Wang, M. Ni, Y. Maeda, T. Wakahara, T. Nakahodo, T. Tsuchiya, T. Akasaka, Z. Gao, D. Yu, H. Ye, W. N. Mei, Y. Zhou, J. Am. Chem. Soc. 2006, 128, 5114-5118, and references therein.
20. a) T. Kawase, H. R. Darabi, M. Oda, Angew. Chem. 1996, 108, 2803-2805;
21. Angew. Chem. Int. Ed. Engl. 1996, 35, 2662-2664;
22. b) T. Kawase, N. Ueda, K. Tanaka, Y. Seirai, M. Oda, Tetrahedron Lett. 2001, 42, 5509-5511;
23. c) T. Kawase, M. Oda, Pure Appl. Chem. 2006, 77, 831-839.
24. T. Kawase, H. R. Darabi, K. Tanaka, M. Oda, Angew. Chem. 2003, 115, 1662-1666;
25. Angew. Chem. Int. Ed. 2003, 42, 1624-1628.
26. T. Kawase, K. Tanaka, N. Shiono, Y. Seirai, M. Oda, Angew. Chem. 2004, 116, 1754-1756;
27. Angew. Chem. Int. Ed. 2004, 43, 1722-1724.
28. Ring-in-ring complexes; a) S. Kamitori, K. Hirotsu, T. Higuchi, J. Am. Chem. Soc. 1987, 109, 2409-2414;
29. b) S.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 2177-2179;
30. Angew. Chem. Int. Ed. 2001, 40, 2119-2121;
31. e) S.-H. Chiu, A. R. Pease, J. F. Stoddart, A. J. P. White, D. Williams, Angew. Chem. 2002, 114, 280-284;
32. Angew. Chem. Int. Ed. 2002, 41, 270-274;
33. d) A. I. Day, R. J. Blanch, R. J. Arnold, G. R. Lewis, I. Dance, Angew. Chem. 2002, 114, 285-287;
34. Angew. Chem. Int. Ed. 2002, 41, 275-277;
35. e) J. C. Loren, M. Yoshizawa, R. F. Haldimann, A. Linden, J. S. Siegel, Angew. Chem. 2003, 115, 5880-5883;
36. Angew. Chem. Int. Ed. 2003, 42, 5702-5705;
37. f) S. J. Dalgarno, J. Fisher, C. L. Raston, Chem. Eur. J. 2006, 12, 2772-2777;
38. g) T. Iwanaga, R. Nakamoto, M. Yasutake, H. Takemura, K. Sako, T. Shinmyozu, Angew. Chem. 2006, 118, 3725-3729;
39. Angew. Chem. Int. Ed. 2006, 45, 3643-3647.
40. Procedures for the synthesis and physical properties of new compounds are shown in the Supporting Information.
41. I. Tabushi, H. Yamada, Y. Kuroda, J. Org. Chem. 1975, 40, 1946-1949.
42. Because of the susceptibility of 1 to oxygen, it is difficult to measure a small quantity of 1 accurately. Thus, the quantity of 1 in chloroform was determined from an NMR spectrum by using adamantane as a standard. The solution in chloroform was diluted about 20-fold with cyclohexane, and the absorption and emission spectra were recorded.
43. a) J. S. Schumm, D. L. Pearson, J. M. Tour, Angew. Chem. 1994, 106, 1445-1449;
44. Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363;
45. b) J. M. Tour, Chem. Rev. 1996, 96, 537-553.
46. K. Hirose, J. Inclusion Phenom. Macrocyclic Chem. 2001, 39, 193-209.
47. a) M. Yanase, M. Matsuoka, Y. Tatsumi, M. Suzuki, H. Iwamoto, T. Haino, Y. Fukazawa, Y. Tetrahedron Lett. 2000, 41, 493-497;
48. b) K. Tashiro, Y. Hirabayashi, T. Aida, K. Saigo, K. Fujiwara, K. Komatsu, S. Sakamoto, K. Yamaguchi, J. Am. Chem. Soc. 2002, 124, 12086-12087;
49. c) T. Haino, M. Yanase, C. Fukunaga, Y. Fukazawa, Tetrahedron 2006, 62, 2025-2035;
50. d) P. E. Georghiou, A. H. Tran, S. S. Stroud, D. W. Thompson, Tetrahedron 2006, 62, 2036-2044.
51. a) F. Diederich, M. Gomez-Lopez, Chem. Soc. Rev. 1999, 28, 263-277;
52. b) M. J. Hardie, C. L. Raston, Chem. Commun. 1999, 1153-1163;
53. c) P. D. W. Boyd, C. A. Reed, Acc. Chem. Res. 2005, 38, 235-242.
54. T. Kawase, H. Kurata, Chem. Rev., 2006, 106, 5250-5273.
55. a) H.-B. Bürgi, E. Blanc, D. Schwarzenbach, S. Lui, Y.-j. Lu, M. M. Kappes, J. A. Ibers, Angew. Chem. 1992, 104, 667-670;
56. Angew. Chem. Int. Ed. Engl. 1992, 31, 640-643;
57. b) A. L. Balch, V. J. Catalano, J. W. Lee, M. M. Olmstead, J. Am. Chem. Soc. 1992, 114, 5455-5456;
58. c) Y. Umezawa, M. Nishio, CrystEngComm 2003, 5, 514-518, and references therein.
59. a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413;
60. b) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Adachi, S. Araki, M. Sonoda, K. Hirose, K. Naemura, J. Am. Chem. Soc. 2002, 124, 5350-5364;
61. c) D. Zhao, J. S. Moore, Chem. Commun. 2003, 807-818;
62. d) S. Höger, Chem. Eur. J. 2004, 10, 1320-1329.
63. a) C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534;
64. b) C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc. Perkin Trans. 2 2001, 651-669;
65. c) E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244-1287;
66. Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
67. The first theoretical study on carbon nanorings: I. Garcia Cuesta, T. B. Pedersen, H. Hoch, A. Sanchez de Meras, ChemPhysChem, 2006, 7, 2503-2507.