Synthesis and spectroscopic studies of arylethynylsilanes

Chemistry - An Asian Journal

Volumn 2, Issue 4, 2007, Pages 489-498

  Shao, Guang ^a   Orita, Akihiro ^a   Nishijima, Koji ^a   Ishimaru, Kanako ^a   Takezaki, Makoto ^a   Wakamatsu, Kan ^a   Gleiter, Rolf ^b   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Alkynes; Conjugation; Fluorescence spectroscopy; Molecular orbitals; Silanes

Indexed keywords

ALKYNE; SILANE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; LUMINESCENCE; SPECTROFLUOROMETRY; SPECTROPHOTOMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ALKYNES; LUMINESCENCE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SILANES; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET; SPIRO COMPOUNDS;

EID: 34249853981     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700007     Document Type: Article

References (75)

1. a) Acetylene Chemistry: Chemistry, Biology, and Material Science (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), VCH, Weinheim, 2005;
2. b) Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim, 1995.
3. a) E. E. Nesterov, Z. Zhu, T. M. Swager, J. Am. Chem. Soc. 2005, 127, 10083;
4. b) C. Kuebel, M. J. Mio, J. S. Moore, D. C. Martin, J. Am. Chem. Soc. 2002, 124, 8605.
5. a) A. J. Zucchero, J. N. Wilson, U. H. F. Bunz, J. Am. Chem. Soc. 2006, 128, 11872;
6. b) W. W. Gerhardt, A. J. Zucchero, J. N. Wilson, C. R. South, U. H. F. Bunz, M. Weck, Chem. Commun. 2006, 2141;
7. c) B. C. Englert, S. Bakbak, U. H. F. Bunz, Macromolecules 2005, 38, 5868;
8. d) E. L. Spitler, L. D. Shirtcliff, M. M. Haley, J. Org. Chem. 2007, 72, 86;
9. e) H. Hinrichs, A. J. Boydston, P. G. Jones, K. Hess, R. Herges, M. M. Haley, Chem. Eur. J. 2006, 12, 7103;
10. f) J. A. Marsden, M. M. Haley, J. Org. Chem. 2005, 70, 10213;
11. g) C. A. Breen, J. R. Tischler, V. Bulovic, T. M. Swager, Adv. Mater. 2005, 17, 1981;
12. h) C. A. Breen, S. Rifai, V. Bulovic, T. M. Swager, Nano Lett. 2005, 5, 1597.
13. a) Y. Jiang, D. Perahia, Y. Wang, U. H. F. Bunz, Macromolecules 2006, 39, 4941;
14. b) H. Hinrich, A. K. Fischer, P. G. Jones, H. Hopf, M. M. Haley, Org. Lett. 2005, 7, 3793;
15. c) K. Tahara, S. Furukawa, H. Uji-i, T. Uchino, T. Ichikawa, J. Zhang, W. Mamdouh, M. Sonoda, F. C. De Schryver, S. De Feyter, Y. Tobe, J. Am. Chem. Soc. 2006, 128, 16613;
16. d) A. Nomoto, M. Sonoda, Y. Yamaguchi, T. Ichikawa, K. Hirose, Y. Tobe, J. Org. Chem. 2006, 71, 401;
17. e) R. Umeda, T. Morinaka, M. Sonoda, Y. Tobe, J. Org. Chem. 2005, 70, 6133;
18. f) M. Sonoda, S. Yu, T. Yoshimura, Y. Tobe, K. Kamada, Chem. Lett. 2004, 33, 972;
19. g) J. W. Wackerly, J. S. Moore, Macromolecules 2006, 39, 7269;
20. h) K. Balakrishnan, A. Datar, W. Zhang, X. Yang, T. Naddo, J. Huang, J. Zuo, M. Yen, J. S. Moore, L. Zang, J. Am. Chem. Soc. 2006, 128, 6576;
21. i) K. Goto, J. S. Moore, Org. Lett. 2005, 7, 1683;
22. j) J. M. Heemstra, J. S. Moore Chem. Commun. 2004, 1480;
23. k) H. Goto, J. M. Heemstra, D. J. Hill, J. S. Moore, Org. Lett. 2004, 6, 889;
24. l) Y. Zhao, Y. Shirai, A. D. Slepkov, L. Cheng, L. B. Alemany, T. Sasaki, F. A. Hegmann, J. M. Tour, Chem. Eur. J. 2005, 11, 3643.
25. A. Orita, L. Jiang, M. Tsuruta, J. Otera, Chem. Lett. 2002, 136.
26. A. Orita, D. L. An, T. Nakano, J. Yaruva, N. Ma, J. Otera, Chem. Eur. J. 2002, 8, 2005.
27. A. Orita, T. Nakano, D. L. An, K. Tanikawa, K. Wakamatsu, J. Otera, J. Am. Chem. Soc. 2004, 126, 10389.
28. S. Kamoji, T. Jin, Y. Yamamoto, Tetrahedron Lett. 2004, 45, 689.
29. B. Wrackmeyer, M. H. Bhatti, S. Ali, O. L. Tok, Y. N. Bubnov, J. Organomet. Chem. 2002, 657, 146.
30. E. Kwon, K. Sakamoto, C. Kabuto, M. Kira, Chem. Lett. 2000, 1416.
31. Reviews of siloles: a) S. Yamaguchi, K. Tamao, J. Chem. Soc. Dalton Trans. 1998, 3693;
32. b) S. Yamaguchi, C. Xu, H. Yamada, A. Wakamiya, J. Organomet. Chem. 2005, 690, 5365;
33. c) A. J. Boydston, B. L. Pagenkopf, Angew. Chem. 2004, 116, 6496;
34. Angew. Chem. Int. Ed. 2004, 43, 6336;
35. d) A. J. Boydston, Y. Yin, B. L. Pagenkopf, J. Am. Chem. Soc. 2004, 126, 10350.
36. H. Maeda, Y. Inoue, H. Ishida, K. Mizuno, Chem. Lett. 2001, 1224.
37. S. Kyushin, M. Ikarugi, M. Goto, H. Hiratsuka, H. Matsumoto, Organometallics 1996, 15, 1067.
38. S. Kyushin, N. Takemasa, H. Matsumoto, H. Horiuchi, H. Hiratsuka, Chem. Lett. 2003, 32, 1048.
39. H. Maeda, T. Maeda, K. Mizuno, K. Fujimoto, H. Shimizu, M. Inoue, Chem. Eur. J. 2006, 12, 824.
40. G. Shao, A. Orita, K. Nishijima, K. Ishimaru, M. Takezaki, K. Wakamatsu, J. Otera, Chem. Lett. 2006, 35, 1284.
41. 3Si and O=C shown by electron transmission spectroscopy: a) A. Modelli, D. Jones, G. Distefano, Chem. Phys. Lett. 1982, 86, 434;
42. b) J. C. Giordan, J. H. Moore, J. Am. Chem. Soc. 1983, 105, 6541;
43. 3Si and C≡C interaction by gas-phase electron diffraction;
44. 3Si and C≡C interaction on Si-H vibration:
45. e) A. N. Egorochkin, N. S. Vyazankin, Doklady Akademii Nauk SSSR 1970, 193, 590.
46. 3: a) R. Gleiter, W. Schäfer, H. Sakurai, J. Am. Chem. Soc. 1985, 107, 3046; interaction between O≡C and aryls on silyl groups:
47. b)K. Igawa, K. Tomooka, Angew. Chem. 2006, 118, 238;
48. Angew. Chem. Int. Ed. 2006, 45, 232.
49. a) A. Orita, H. Taniguchi, J. Otera, Chem. Asian J. 2006, 1, 430;
50. b) A. Orita, K. Miyamoto, M. Nakashima, F. Ye, J. Otera, Adv. Synth. Catal. 2004, 346, 767;
51. c) A. Orita, T. Nakano, T. Yokoyama, G. Babu, J. Otera, Chem. Lett. 2004, 33, 1298;
52. d) F. Ye, A. Orita, J. Yaruva, T. Hamada, J. Otera, Chem. Lett. 2004, 33, 528;
53. e) F. Ye, A Orita, A. Doumoto, J. Otera, Tetrahedron 2003, 59, 5635;
54. f) A. Orita, F. Ye, A. Doumoto, J. Otera, Chem. Lett. 2003, 32, 104;
55. g) A. Orita, D. Hasegawa, T. Nakano, J. Otera, Chem. Eur. J. 2002, 8, 2000;
56. h) A. Orita, N. Yoshioka, P. Struwe, A. Braier, A. Beckmann, J. Otera, Chem. Eur. J. 1999, 5, 1355.
57. H. Matsumoto, K. Akaiwa, Y. Nagai, K. Ohno, K. Imai, S. Masuda, Y. Harada, Organometallics 1986, 5, 1526.
58. T. Koopmans, Physica (Amsterdam) 1933, 1, 104.
59. a) A. Riemann, R. W. Hoffmann, J. Spanget-Larsen. R. Gleiter. Chem, Ber. 1985, 118, 1000;
60. b) M. D. Gordon, T. Fukunaga, H. E. Simmons, J. Am. Chem. Soc. 1976, 98, 84041.
61. a) A. Schweig, U. Weidner, D. Hellwinkel, W. Krapp, Angew. Chem. 1973, 85, 360;
62. 2-Ar';
63. b) C. A. van Walree, M. R. Roest, W. Schuddeboom, L. W. Jenneskens, J. W. Verhoeven, J. M. Warman, H. Kooijman, A. L. Spek, J. Am. Chem. Soc. 1996, 118, 8395.
64. P) has been reported as well; see reference [14] and the following: S. Kyushin, T. Kitahara, H. Matsumoto, Chem. Lett. 1998, 471.
65. Spartan 04 (Wavefunction, Inc.) and Gaussian 03 (Gaussian, Inc.) were used for computational analysis. In the Supporting Information of reference [16], the HOMOs and LUMOs of 16 and 17 are shown for comparison. Because these two compounds have infinite conformers that can interconvert readily due to free rotation of C-(phenyl)-C(acetylene), we used the conformer in Figure 10 as a feasible example.
66. a) K. S. Feldman, C. M. Kraebel, M. Parvez, J. Am. Chem. Soc. 1993, 115, 3846;
67. b) K. S. Feldman, C. K. Weinreb, W. J. Youngs, J. D. Brandshaw, J. Org. Chem. 1994, 59, 1213;
68. c) K. S. Feldman, C. K. Weinreb, W. J. Youngs, J. D. Brandshaw, J. Am. Chem. Soc. 1994, 116, 9019.
69. R. Amemiya, K. Suwa, J. Toriyama, Y. Nishimura, M. Yamaguchi, J. Am. Chem. Soc. 2005, 127, 8252.
70. B. Ma, H. M. Sulzbach, Y. Xie, H. F. Schaefer III, J. Am. Chem. Soc. 1994, 116, 3529.
71. M. Takezaki, T. Tominaga, J. Photochem. Photohiol. A 2005, 774, 113-118.
72. M. Tsuji, J. Org. Chem. 2003, 68, 9589.
73. B. Wrackmeyer, O. L. Tok, A. Badshah, Z. Naturforsch. 2003, 58b, 809.
74. Z. Xi, R. Fischer, R. Hara, W.-H. Sun, Y. Obora, N. Suzuki, K. Nakajima, T. Takahashi, J. Am. Chem. Soc. 1997, 119, 12842.
75. A. Kovalev, K. Takeuchi, J-I. Sugiyama, M. Goyal, R. Nagahata, M. Asai, A. V. Barzykin, M. Ueda, A. L. Rusanov, High Perform. Polym. 2004, 16, 447.