Synthesis of nonaphenylenes and dodecaphenylenes using electron-transfer oxidation of Lipshutz cuprates and formation of nanostructural materials from hexadodecyloxynonaphenylene

Journal of Organic Chemistry

Volumn 73, Issue 14, 2008, Pages 5542-5548

  Rahman, M Jalilur ^a   Yamakawa, Jun ^a   Matsumoto, Aoi ^a   Enozawa, Hideo ^a   Nishinaga, Tohru ^a   Kamada, Kenji ^b   Iyoda, Masahiko ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; AROMATIC COMPOUNDS; BENZENE; CHEMICAL OXYGEN DEMAND; CHEMICAL REACTIONS; COPPER COMPOUNDS; CRYSTALLOGRAPHY; EMISSION SPECTROSCOPY; ETHERS; FIBER OPTICS; FIBERS; FLUORESCENCE; LIGHT EMISSION; LUMINESCENCE; NANOFIBERS; NANOSTRUCTURED MATERIALS; NANOSTRUCTURES; NONMETALS; ORGANIC COMPOUNDS; OXIDATION; OXYGEN; SILICON; SURFACES; THICK FILMS; X RAY ANALYSIS; X RAY DIFFRACTION ANALYSIS;

ABSORPTION MAXIMUM; AMERICAN CHEMICAL SOCIETY (ACS); AROMATIC RINGS; ATMOSPHERIC OXYGEN; CHEMICAL EQUATIONS; CHLOROFORM (CF); CUPRATE; CUPRATES; DIISOPROPYL ETHER (DIPE); ELECTRON-TRANSFER OXIDATION; EMISSION MAXIMA; EMISSION SPECTRUMS; FLUORESCENCE ANISOTROPY (FA); FLUORESCENCE INTENSITY (FI); FLUORESCENT EMISSIONS; LONGITUDINAL AXIS; NANO FIBERS; NANOSTRUCTURAL MATERIALS; NITRO-AROMATICS; O TERPHENYL (OTB); OLIGOPHENYLENES; REDOX PROPERTIES; SILICON (0 0 1) SURFACES; STACKING INTERACTIONS; STACKING STRUCTURES; STARTING MATERIALS; TERPHENYLS; UV ABSORPTIONS; X-RAY DIFFRACTION (XRD) PATTERNS; XRD ANALYSIS;

SPINNING (FIBERS);

BENZENE; BENZENE DERIVATIVE; BENZYL [1 [1 (6 METHOXYBENZOTHIAZOL 2 YLCARBAMOYL)ETHYLCARBAMOYL] 2 PHENYLETHYL] CARBAMATE; BENZYL N[1 (1H INDOL 3 YLMETHYL) 2 OXO 2 (1,3 THIAZOL2 YLAMINO)ETHYL]CARBAMATE; CHLOROFORM; CYCLOHEXENE DERIVATIVE; DIISOPROPYL ETHER; DUROQUINONE; NANOFIBER; NANOMATERIAL; OXYGEN; SILICON;

ABSORPTION; ANISOTROPY; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; HEATING; LIGHT ABSORPTION; OXIDATION; OXIDATION REDUCTION POTENTIAL; SYNTHESIS; VAPOR; X RAY DIFFRACTION;

EID: 48249135696     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800787u     Document Type: Article

References (115)

1. For recent examples, see: (a) Matsubara, H.; Yoshimoto, S.; Saito, H.; Jianglin, Y.; Tanaka, Y.; Noda, S. Science 2008, 319, 445-447.
2. (b) Shvets, G. Nat. Mater. 2008, 7, 7-8.
3. (c) Nesbitt, D. J. Nature 2007, 450, 1172-1173.
4. (d) Yeom, D.-I.; Eggleton, B. J. Nature 2007, 450, 953-954.
5. (e) Lu, C.; Dimov, S. S.; Lipson, R. H. Chem. Mater. 2007, 19, 5018-5022.
6. (f) Busch, K.; von Freymann, G.; Linden, S.; Mingaleev, S. F.; Tkeshelashvili, L.; Wegener, M. Phys. Rep. 2007, 444, 101-202.
7. (a) Staab, H. A.; Binnig, F. Chem. Ber. 1967, 100, 293-305.
8. (b) Meyer, H.; Staab, H. A. Liebigs Ann. 1969, 724, 30-33.
9. (c) Irngartinger, H.; Leiserowitz, L.; Schmidt, G. M. J. Chem. Ber. 1970, 103, 1132-1156.
10. (d) Wittig, G.; Rümpler, K.-D. Liebigs Ann. 1971, 751, 1-16.
11. (e) Fujioka, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3494-3506.
12. (f) Cram, D. J.; Kaneda, T.; Helgeson, R. C.; Brown, S. B.; Knobler, C. B.; Maverick, E.; Trueblood, K. N. J. Am. Chem. Soc. 1985, 107, 3645-3657.
13. (g) Chan, C. W.; Wong, H. N. C. J. Am. Chem. Soc. 1985, 107, 4790-4791.
14. (h) Chan, C. W.; Wong, H. N. C. J. Am. Chem. Soc. 1988, 110, 462-469.
15. (i) König, B.; Heinze, J.; Meerholz, J. K.; de Meijere, A. Angew. Chem., Int. Ed. 1991, 30, 1361-1363.
16. (j) Percec, V.; Okita, S. J. Polym. Sci., Polym. Chem. Ed. 1993, 31, 877-884.
17. (k) Wong, T.; Yuen, M. S. M.; Mak, T. C. W.; Wong, H. N. C. J. Org. Chem. 1993, 58, 3118-3122.
18. (l) Rajca, A.; Safronov, A.; Rajca, S.; Shoemaker, R. Angew. Chem., Int. Ed. 1997, 36, 488-491.
19. (m) Hensel, V.; Lützow, K.; Schlüter, A.-D.; Jacob, J.; Gessler, K.; Saenger, W. Angew. Chem., Int. Ed. 1997, 36, 2654-2656.
20. (n) Kelly, T. R.; Lee, Y.-J.; Mears, R. J. J. Org. Chem. 1997, 62, 2774-2781.
21. (o) Hensel, V.; Schlüter, A. D. Chem. Eur. J. 1999, 5, 421-429.
22. (p) Peng, H.-Y.; Lam, C.-K.; Mak, T. C. W.; Cai, Z.; Ma, W.-T.; Li, Y.-X.; Wong, H. N. C. J. Am. Chem. Soc. 2005, 127, 9603-9611.
23. (q) Stuparu, M.; Gramlich, V.; Stanger, A.; Schlüter, A. D. J. Org. Chem. 2007, 72, 424-430.
24. (r) Pisula, W.; Kastler, M.; Yang, C.; Enkelmann, V.; Müllen, K. Chem. Asian J. 2007, 2, 51-56.
25. (a) Pascal, R. A., Jr. Chem. Rev. 2006, 106, 4809-4819.
26. (b) Herges, R. Chem. Rev. 2006, 106, 4820-4842.
27. (c) Wu, Y.-T.; Siegel, J. S. Chem. Rev. 2006, 106, 4843-4867.
28. (d) Tsefrikas, V. M.; Scott, L. T. Chem. Rev. 2006, 106, 4868-4884.
29. (e) Kawase, T.; Kurata, H. Chem. Rev. 2006, 106, 5250-5273.
30. (f) Tahara, K.; Tobe, Y. Chem. Rev. 2006, 106, 5274-5290.
31. (g) Carbon-Rich Compounds From Molecules to Materials; Haley, M. M., Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
32. (h) Molecular Devices and Machines; Balzani, V., Venturi, M., Credi, A., Eds.; Wiley-VCH: Weinheim, Germany, 2003.
33. (i) Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
34. (j) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
35. (a) Al-Matar, H.; Abdul-Sada, A. K.; Avent, A. G.; Taylor, R. Org. Lett. 2001, 3, 1669-1671.
36. (b) Murata, Y.; Murata, M.; Komatsu, K. J. Org. Chem. 2001, 66, 8187-8191.
37. (c) Vougioukalakis, G. C.; Prassides, K.; Orfanopoulos, M. Org. Lett. 2004, 6, 1245-1247.
38. (d) Stanisky, C. M.; Cross, R. J.; Saunders, M.; Murata, M.; Murata, Y.; Komatsu, K. J. Am. Chem. Soc. 2005, 107, 299-302.
39. (e) Huang, S.; Wang, F.; Gan, L.; Yuan, G.; Zhou, J.; Zhang, S. Org. Lett. 2006, 8, 277-247.
40. (a) Höger, S. J. Polym. Sci. Part A 1999, 37, 2685-2698.
41. (b) Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 807-818.
42. (c) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807-818.
43. (d) Yamaguchi, Y.; Yoshida, Z. Chem. Eur. J. 2003, 9, 5430-5440.
44. (e) Höger, S. Angew. Chem., Int. Ed. 2005, 44, 3806-3808.
45. (f) Schlüter, A. D. Top. Curr. Chem. 2005, 245, 151-191.
46. Zhang, W.; Moore, J. S. Angew. Chem., Int. Ed. 2006, 45, 4416-4439.
47. (a) Winkler, H. J. S.; Wittig, G. J. Org. Chem. 1963, 28, 1733-1740.
48. (b) Wittig, G.; Fischer, S.; Günther, R. Liebigs Ann. 1973, 495-498.
49. Fujioka, Y. Bull. Chem. Soc. Jpn. 1985, 58, 481-489.
50. Cepanec, I. Synthesis of Biaryls; Elsevier: Oxford, UK, 2004.
51. For recent reviews, see: (a) Negishi, E.-I. Bull. Chem. Soc. Jpn. 2007, 80, 233-257.
52. (b) de Meijere, A.; Stulgies, B.; Albrecht, K.; Rauch, K.; Wagner, H. A. Pure Appl. Chem. 2006, 78, 813-830.
53. (c) Zapf, A. Angew. Chem., Int. Ed. 2003, 42, 5394-5399.
54. (d) Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717-727.
55. Kauffmann, T. Angew. Chem. 1974, 86, 321-335.
56. (a) Iyoda, M.; Otsuka, H.; Sato, K.; Nisato, N.; Oda, M. Bull. Chem. Soc. Jpn. 1990, 63, 80-87.
57. (b) Iyoda, M.; Sato, K.; Oda, M. Chem. Commun. 1985, 1547-1548.
58. (c) Iyoda, M.; Sato, K.; Oda, M. Tetrahedron Lett. 1985, 26, 3829-3833.
59. (a) Iyoda, M.; Kabir, S. M. H.; Vorasingha, A.; Kuwatani, Y.; Yoshida, M. Tetrahedron Lett. 1998, 39, 5393-5396.
60. (b) Kabir, S. M. H.; Miura, M.; Sasaki, S.; Harada, G.; Kuwatani, Y.; Yoshida, M.; Iyoda, M. Heterocycles 2000, 52, 761-774.
61. (c) Kabir, S. M. H.; Hasegawa, M.; Kuwatani, Y.; Yoshida, M.; Matsuyama, H.; Iyoda, M. J. Chem. Soc., Perkin Trans. 1 2001, 159-165.
62. (a) Iyoda, M.; Kondo, T.; Nakao, K.; Hara, K.; Kuwatani, Y.; Yoshida, M.; Matsuyama, H. Org. Lett. 2000, 2, 2081-2083.
63. (b) Harada, G.; Yoshida, M.; Iyoda, M. Chem. Lett. 2000, 160-161.
64. (a) Miyake, Y.; Wu, M.; Rahman, M. J.; Iyoda, M. Chem. Commun. 2005, 411-413.
65. (b) Miyake, Y.; Wu, M.; Rahman, M. J.; Kuwatani, Y.; Iyoda, M. J. Org. Chem. 2006, 71, 6110-6117.
66. For the electron-transfer oxidation of organometallics, see: (a) Cheng, J.-W.; Luo, F.-T. Tetrahedron Lett. 1988, 29, 1293-1294.
67. (b) Chen, C.; Xi, C.; Lai, C.; Wang, R.; Hong, X. Eur. J. Org. Chem. 2004, 647-650.
68. (a) Boche, G.; Bosold, F.; Marsch, M.; Hanns, K. Angew. Chem., Int. Ed. 1998, 37, 1684-1686.
69. (b) Kronenburg, C. M. P.; Jastrzebski, J. T. B. H.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1998, 120, 9688-9689.
70. (c) Krause, N. Angew. Chem., Int. Ed. 1999, 38, 79-81.
71. (d) Hwang, C.-S.; Power, P. P. J. Am. Chem. Soc. 1998, 120, 6409-6410.
72. Iyoda, M.; Rahman, M. J.; Matsumoto, A.; Wu, M.; Kuwatani, Y.; Nakao, K.; Miyake, Y. Chem. Lett. 2005, 34, 1474-1475.
73. 3 solutions to sunlight for several hours or prolonged heating at 160°C under air. The thermal gravity (TG) analysis of 1e showed the decomposition at 350°C.
74. (a) Giordani, R.; Buc, J. Eur. J. Biochem. 2004, 271, 2400-2407.
75. (b) Pasimeni, L.; Brustolon, M.; Corvaja, C. J. Chem. Soc., Faraday Trans. 2 1972, 68, 223-233.
76. (c) Gough, T. E.; Hindle, P. R. Can. J. Chem. 1969, 47, 1698-1700.
77. (a) Cao, X.-Y.; Zi, H. Y.; Zhang, W.; Lu, H.; Pei, J. J. Org. Chem. 2005, 70, 3645-3653.
78. (b) Holman, M. W.; Liu, R.; Zang, L.; Yan, P. J. Am. Chem. Soc. 2004, 126, 16126-16133.
79. (c) Li, Z. H.; Wong, M. S.; Tao, Y.; D'Iorio, M. J. Org. Chem. 2004, 69, 921-927.
80. Bonesi, S. M.; Erra-Balsells, R. J. Chem. Soc., Perkin Trans. 2 2000, 1583-1595.
81. (a) Munakata, M.; Wu, L. P.; Ning, G. L.; Kuroda-Sowa, T.; Maekawa, M.; Suenaga, Y.; Maeno, N. J. Am. Chem. Soc. 1999, 121, 4968-4976.
82. (b) Iyoda, M.; Kuwatani, Y.; Yamauchi, T.; Oda, M. Chem. Commun. 1988, 65-66.
83. (c) Iyoda, M.; Horino, T.; Takahashi, F.; Hasegawa, M.; Yoshida, M.; Kuwatani, Y. Tetrahedron Lett. 2001, 42, 6883-6886.
84. (a) Pierre, J.-L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986-2988.
85. (b) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boekelheide, V. J. Am. Chem. Soc. 1985, 107, 1979-1985.
86. (c) Sirinintasak, S.; Kuwatani, Y.; Hoshi, S.; Isomura, E.; Nishinaga, T.; Iyoda, M. Tetrahedron Lett. 2007, 48, 3433-3436.
87. (a) Ajyayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656.
88. (b) Shimizu, T.; Masuda, M.; Minamikawa, H. Chem. Rev. 2005, 105, 1401-1443.
89. (c) Hoeben, F. M. J.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
90. (d) Grimsdale, A. C.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 5592-5629.
91. (e) Ishi-i, T.; Shinkai, S. Top. Curr. Chem. 2005, 258, 119-160.
92. (f) Sangeetha, N. M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821-836.
93. (a) Yamamoto, Y.; Fukushima, T.; Suna, Y.; Ishii, N.; Saeki, A.; Seki, S.; Tagawa, S.; Taniguchi, M.; Kawai, T.; Aida, T. Science 2006, 314, 1761-1764.
94. (b) Sly, J.; Kasák, P.; Gomar-Nadal, E.; Rovira, C.; Górriz, L.; Thorarson, P.; Amabilino, D. B.; Rowan, A. E.; Nolte, R. J. M. Chem. Commun. 2005, 1255-1257.
95. (c) Akutagawa, T.; Kakiuchi, K.; Hasegawa, T.; Noro, S.; Nakamura, T.; Hasegawa, H.; Mashiko, S.; Becher, J. Angew. Chem., Int. Ed. 2005, 44, 7283-7287.
96. (d) Kitamura, T.; Nakaso, S.; Mizoshita, N.; Tochigi, Y.; Shimomura, T.; Moriyama, M.; Ito, K.; Kato, T. J. Am. Chem. Soc. 2005, 127, 14769-14775.
97. (e) Puigmarti-Luis, J.; Laukhin, V.; Del Pino, A. P.; Vidal-Gancedo, J.; Rovira, C.; Laukhina, E.; Amabilino, D. B. Angew. Chem., Int. Ed. 2007, 46, 238-241.
98. (a) Hasegawa, M.; Enozawa, H.; Kawabata, Y.; Iyoda, M. J. Am. Chem. Soc. 2007, 129, 3072-3073.
99. (b) Kobayashi, Y.; Hasegawa, M.; Enozawa, H.; Iyoda, M. Chem. Lett. 2007, 36, 720-721.
100. (c) Nakao, K.; Nishimura, M.; Tamachi, T.; Kuwatani, Y.; Miyasaka, H.; Nishinaga, T.; Iyoda, M. J. Am. Chem. Soc. 2006, 128, 16740-16747.
101. (a) Kastler, M.; Pisula, W.; Wasserfallen, D.; Pakula, T.; Müllen, K. J. Am. Chem. Soc. 2005, 127, 4286-4296.
102. (b) Balakrishnan, K.; Datar, A.; Zhang, W.; Yang, X.; Naddo, T.; Huang, J.; Zuo, J.; Yen, M.; Moore, J. S.; Zang, L. J. Am. Chem. Soc. 2006, 128, 6576-6577.
103. (c) Enozawa, H.; Hasegawa, M.; Takamatsu, D.; Fukui, K.; Iyoda, M. Org. Lett. 2006, 8, 1917-1920.
104. Although 1e forms nanostructures, 1a, 1b, and 2b precipitate as crystals and 1e, 1d, 2c, and 2d form microcrystals from solution.
105. (a) Fainberg, A. Science 1992, 255, 1531-1537.
106. (b) Swager, T. M. Acc. Chem. Res. 1998, 31, 201-207.
107. (c) Steinfeld, J. I.; Wormhoudt, J. Annu. Rev. Phys. Chem. 1998, 49, 203-232.
108. (a) Yang, J.-S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873.
109. (b) Chen, L.; McBranch, D.; Wang, R.; Whitten, D. Chem. Phys. Lett 2000, 330, 27-33.
110. (c) Sohn, H.; Sailor, M. J.; Magde, D.; Trogler, W. C. J. Am. Chem. Soc. 2003, 125, 3821-3830.
111. (d) Liu, Y.; Mills, R. C.; Boncella, J. M.; Schanze, K. S. Langmuir 2001, 17, 7452-7455.
112. (e) Goldman, E. R.; Medintz, I. L.; Whitley, J. L.; Hayhurst, A.; Clapp, A. R.; Uyeda, H. T.; Deschamps, J. R.; Lassman, M. E.; Mattoussi, H. J. Am. Chem. Soc. 2005, 127, 6744-6781.
113. (f) Naddo, T.; Che, Y.; Zhang, W.; Balakrishnan, K.; Yang, X.; Yen, M.; Zhao, J.; Moore, J. S.; Zang, L. J. Am. Chem. Soc. 2007, 129, 6978-6979.
114. (g) Narayanan, A.; Varnavski, O. P.; Swager, T. M.; Goodson, T., III J. Phys. Chem. C 2008, 112, 881-884.
115. Under reduced pressure (∼2 mmHg) for 1 h, over 98% of emission of the 1e film was regenerated (see the Supporting Information).