Synthesis, structure, and electronic and photophysical properties of two- and three-layered [3.3]Paracyclophane-based donor-acceptor systems (1)

Journal of Organic Chemistry

Volumn 75, Issue 18, 2010, Pages 6104-6114

  Watanabe, Motonori ^a   Goto, Kenta ^a   Shibahara, Masahiko ^b   Shinmyozu, Teruo ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b OITA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE RING; BENZOTHIADIAZOLES; COUPLING METHODS; CYCLIC VOLTAMMOGRAMS; DONOR-ACCEPTOR SYSTEM; DONOR-ACCEPTORS; ELECTRONIC INTERACTIONS; FLUORESCENCE BAND; ISOCYANIDES; PARACYCLOPHANE; PHOTOPHYSICAL PROPERTIES; SHARP CONTRAST; THROUGH-BOND INTERACTIONS; THROUGH-SPACE INTERACTION; UV/VIS SPECTRA;

BENZENE; CHARGE TRANSFER; CYANIDES; GROUND STATE; QUANTUM YIELD;

QUANTUM THEORY;

(4 ETHYLBENZENESULFONYL)METHYLISOCYANIDE; 2,1,3 BENZOTHIADIAZOLE; [3.3]PARACYCLOPHANE; CYCLOHEXANE; PARACYCLOPHANE DERIVATIVE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; FLUORESCENCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; QUANTUM YIELD; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET RADIATION;

CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; MODELS, MOLECULAR; MOLECULAR DYNAMICS SIMULATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMISTRY; POLYCYCLIC COMPOUNDS; QUANTUM THEORY; STEREOISOMERISM;

EID: 77956536202     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100688m     Document Type: Article

References (66)

1. Donor-Bridge-Acceptor System. 1.
2. Balzani, V., Credi, A., and Venturi, M. In Molecular Devices and Machines; Wiley-VCH: New York, 2008; pp 33 - 63.
3. Paddon-Row, M. Acc. Chem. Res. 1994, 27, 18-25
4. Jordan, K. D.; Paddon-Row, M. Chem. Rev. 1992, 92, 395-410
5. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205
6. James, D. K.; Tour, J. M. Top. Curr. Chem. 2005, 257, 33-62
7. Weiss, E. A.; Wasielewski, M. R.; Ratner, M. R. Top. Curr. Chem. 2005, 257, 103-133
8. Murphy, C. J.; Arkin, M. R.; Jenkins, Y.; Ghatlia, N. D.; Bossmann, S. H.; Turro, N. J.; Barton, J. K. Science 1993, 262, 1025-1029
9. Kelley, S. O.; Barton, J. K. Science 1999, 283, 375-381
10. Lewis, F.; Letsinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159-170
11. Giese, B. Annu. Rev. Biochem. 2002, 71, 51-70
12. Takada, T.; Kawai, K.; Fujitsuka, M.; Majima, T. Chem. - Eur. J. 2005, 11, 3835-3842
13. Boussicault, F.; Robert, M. Chem. Rev. 2008, 108, 2622-2645
14. Vura-Weis, J.; Wasielewski, M. R.; Thazhathveetil, A. K.; Lewis, F. D. J. Am. Chem. Soc. 2009, 131, 9722-9727
15. Nakano, T.; Yade, T.; Yokoyama, M.; Nagayama, N. Chem. Lett. 2004, 33, 296-297
16. Nakano, T.; Yade, T. J. Am. Chem. Soc. 2003, 125, 15474-15484
17. Morisaki, Y.; Murakami, T.; Sawamura, T.; Chujo, Y. Macromolecules 2009, 42, 3656-3660
18. Zeida, T. A.; Wang, Q.; Fiebig, T.; Lewis, F. D. J. Am. Chem. Soc. 2007, 129, 9848-9849
19. Lewis, F. D.; Daublain, P.; Santos, G. B. D.; Liu, W.; Asatryan, A. M.; Markarian, S. A.; Fiebig, T.; Raytchev, M.; Wang, Q. J. Am. Chem. Soc. 2006, 128, 4792-4801
20. Rathore, R.; Abdelwahed, S. H.; Guzei, I. A. J. Am. Chem. Soc. 2003, 125, 8712-8713
21. Nakano, T.; Yade, T. Chem. Lett. 2008, 37, 258-259
22. Shibahara, M.; Watanabe, M.; Iwanaga, T.; Matsumoto, T.; Ideta, K.; Shinmyozu, T. J. Org. Chem. 2008, 73, 4433-4442
23. Atsuya, M.; Shibahara, M.; Watanabe, M.; Matsumoto, T.; Shinmyozu, T.; Kobayashi, N. J. Org. Chem. 2008, 73, 9125-9128
24. Shibahara, M.; Watanabe, M.; Iwanaga, T.; Ideta, K.; Shinmyozu, T. J. Org. Chem. 2007, 72, 2865-2877
25. Shibahara, M.; Watanabe, M.; Aso, K.; Shinmyozu, T. Synthesis 2008, 23, 3749-3754
26. Shibahara, M.; Watanabe, M.; Suenaga, M.; Ideta, K.; Matsumoto, T.; Shinmyozu, T. Tetrahedron Lett. 2009, 50, 1253-1260
27. Akhtaruzzaman, Md.; Tomura, M.; Nishida, J.; Yamashita, Y. J. Org. Chem. 2004, 69, 2953-2958
28. Clark, P. A.; Gleiter, R.; Hilbronner, E. Tetrahedron 1973, 29, 3085-3089
29. Fujita, M.; Ishida, A.; Majima, T.; Takamuku, S. J. Phys. Chem. 1996, 100, 5382-5387
30. Shida, T. Electronic Absorption Spectra of Radical Ions; Elsevier: Amsterdam, 1988.
31. Watanabe, M.; Goto, K.; Fujitsuka, M.; Tojo, S.; Majima, T.; Shinmyozu, T. Bull. Chem. Soc. Jpn., in press.
32. Fujitsuka, M.; Samori, S.; Hara, M.; Tojo, S.; Yamashiro, S.; Shinmyozu, T.; Majima, T. J. Phys. Chem. A 2005, 109, 3531-3534
33. Fujitsuka, M.; Cho, D. W.; Tojo, S.; Yamashiro, S.; Shinmyozu., T.; Majima, T. J. Phys. Chem. A 2006, 110, 5735-5739
34. Fujitsuka, M.; Tojo, S.; Shinmyozu, T.; Majima, T. Chem. Commun. 2009, 1553-1555
35. Staab, H. A.; Zapf, U.; Gurke, A. Angew. Chem., Int. Ed. Engl. 1977, 16, 801-803
36. Staab, H. A.; Zapf, U. Angew. Chem., Int. Ed. Engl. 1978, 17, 757-758
37. Machida, H.; Tatemithu, H.; Otsubo, T.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1980, 53, 2943-2952
38. Staab, H. A.; Feurer, A.; Hauck, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2428-2431
39. Stabb, H. A.; Terecel, M.; Fischer, R.; Krieger, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1463-1646
40. Staab, H. A.; Wahl, P.; Kay, K. Y. Chem. Ber. 1987, 120, 541-549
41. Staab, H. A.; Krieger, C.; Wahl, P.; Kay, K. Y. Chem. Ber. 1987, 120, 551-558
42. Tatemitsu, H.; Natsume, B.; Yoshida, M.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1978, 19, 3459-3462
43. Staab, H. A.; Knaus, G. H.; Henke, H. E.; Krieger, C. Chem. Ber. 1983, 116, 2785-2807
44. Staab, H. A.; Hinz, R.; Knaus, G. H.; Krieger, C. Chem. Ber. 1983, 116, 2835-2847
45. Pesin., V. G.; D'yachenko, E. K. Khim. Geterotsikl. Soed. 1967, 6, 1048-1052
46. Pauling, L. The Nature of the Chemical Bonds; Cornell University Press: Ithaca, NY, 1960; p 260.
47. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
48. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
49. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
51. Sako, K.; Tatemitsu, H.; Onaka, S.; Takemura, H.; Osada, S.; Wen, G.; Rudzinski, J. M.; Shinmyozu, T. Liebigs Ann. 1996, 1645-1649
52. Newkome, G. R.; Pappalardo, S.; Fronczek, F. R. J. Am. Chem. Soc. 1983, 105, 5152-5153
53. Voegtle, F.; Koesgen, U. U.; Puff, H.; Reuter, H. Chem. Ber. 1989, 122, 343-346
54. Gantzal, P. K.; Trueblood, K. N. Acta Crystallogr. 1965, 18, 958-968
55. Furo, T.; Mori, T.; Wada, T.; Inoue, Y. J. Am. Chem. Soc. 2005, 127, 8242-8243
56. Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1988, 153, 503-506
57. Yasutake, M.; Koga, T.; Sakamoto, Y.; Komatsu, S.; Zhou, M.; Sako, K.; Tatemitsu, H.; Onaka, S.; Aso, Y.; Inoue, S.; Shinmyozu, T. J. Am. Chem. Soc. 2002, 1246, 10136-10145
58. The CV profiles of the intermolecular CT complexes between the parent two- and three-layered [3.3]PCPs and TCNE show both oxidation process of the cyclophane moiety and reduction process of TCNE (Figures S28 and S29, Supporting Information). The oxidation potentials of the [3.3]PCP moieties of the complexes are similar to the corresponding oxidation potentials of the free [3.3]PCPs, suggesting the very weak electronic interaction between the [3.3]PCPs and TCNE under the conditions.
59. 2 solution's potential window, the reduction process was observed in THF, in which 2 shows a higher reduction potential than 1 (Figure S30, Supporting Information).
60. Nogita, R.; Matohara, K.; Yamaji, M.; Oda, T.; Sakamoto, Y.; Kumagai, T.; Lim, C.; Yasutake, M.; Shimo, T.; Jefford, C. W.; Shinmyozu, T. J. Am. Chem. Soc. 2004, 126, 13732-13741
61. Stratmann, R. E.; Scuseria; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224
62. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464
63. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449
64. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
65. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119
66. Crystal Structure Analysis Package; Molecular Structure Corp.: The Woodlands, TX, 1985, 1999.