Pure and Applied Chemistry

Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 917-929

http://dx.doi.org/10.1351/PAC-CON-11-09-07

Published online 2012-02-09

Construction of novel molecular architectures from anthracene units and acetylene linkers

References

• 1a. C. Weder (Ed.). Poly(arylene ethynylene)s, Springer, Heidelberg (2005).
• 1b. M. Leclerc, J.-F. Morin (Eds.). Design and Synthesis of Conjugated Polymers, Wiley-VCH, Weinheim (2010).
• 1c. B.-B. Ni, Q. Yan, Y. Ma, D. Zhao. Coord. Chem. Rev. 254, 954 (2010). (http://dx.doi.org/10.1016/j.ccr.2010.02.004)
• 2a. K. Sonogashira. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, E.-i. Negishi, A. de Meijere (Eds.), p. 493, John Wiley, New York (2002).
• 2b. R. Chinchilla, C. Nájera. Chem. Rev. 107, 874 (2007). (http://dx.doi.org/10.1021/cr050992x)
• 2c. P. Simemsen, R. C. Livingston, F. Diederich. Angew. Chem., Int. Ed. 39, 2632 (2000).
• 3. N. M. Jenny, M. Mayor, T. R. Eaton. Eur. J. Org. Chem. 4965 (2011). (http://dx.doi.org/10.1002/ejoc.201100176)
• 4a. E. L. Spitler, C. A. Johnson II, M. M. Haley. Chem. Rev. 106, 5344 (2006). (http://dx.doi.org/10.1021/cr050541c)
• 4b. K. Tahara, T. Yoshimura, M. Sonoda, Y. Tobe, R. V. Williams. J. Org. Chem. 72, 1437 (2007). (http://dx.doi.org/10.1021/jo0622781)
• 5a. T. Kawase. Synlett 2609 (2007). (http://dx.doi.org/10.1055/s-2007-991078)
• 5b. W. Zhang, J. S. Moore. Angew. Chem., Int. Ed. 45, 4416 (2006). (http://dx.doi.org/10.1002/anie.200503988)
• 5c. Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Adachi, S. Araki, M. Sonoda, K. Hirose, K. Naemura. J. Am. Chem. Soc. 124, 5350 (2002). (http://dx.doi.org/10.1021/ja012458m)
• 5d. S. Höger. Chem.—Eur. J. 10, 1320 (2004). (http://dx.doi.org/10.1002/chem.200305496)
• 6a. V. Balzani, M. Benturi, A. Credi. Molecular Devices and Machines, Wiley-VCH, Weinheim (2003).
• 6b. Y. Shirai, J.-F. Morin, T. Sasaki, J. M. Guerrero, J. M. Tour. Chem. Soc. Rev. 35, 1043 (2006). (http://dx.doi.org/10.1039/b514700j)
• 6c. T. C. Bedard, J. S. Moore. J. Am. Chem. Soc. 117, 10662 (1995). (http://dx.doi.org/10.1021/ja00148a008)
• 7a. Y. Zhao, J. S. Moore. In Foldamers: Structure, Properties, and Applications, S. Hecht, I. Huc (Eds.), Chap. 3, Wiley-VCH, Weinheim (2007).
• 7b. M. M. Slutsky, J. S. Phillip, G. N. Tew. New J. Chem. 32, 670 (2008). (http://dx.doi.org/10.1039/b707618e)
• 8a. S. W. Thomas III, G. D. Joly, T. M. Swager. Chem. Rev. 107, 1339 (2007). (http://dx.doi.org/10.1021/cr0501339)
• 8b. M. Leclerc, J.‑F. Morin (Eds.). Design and Synthesis of Conjugated Polymers, Chap. 5, Wiley-VCH, Weinheim (2010).
• 8c. U. H. F. Bunz. Macromol. Rapid Commun. 30, 772 (2009). (http://dx.doi.org/10.1002/marc.200800775)
• 9. Y. Tobe, M. Sonoda. In Modern Cyclophane Chemistry, R. Gleiter, H. Hopf (Eds.), Chap 1, Wiley-VCH, Weinheim (2004).
• 10. Recent examples of oligomers with anthracene units.
• 10a. S. Chen, Q. Yan, T. Li, D. Zhao. Org. Lett. 12, 4784 (2010). (http://dx.doi.org/10.1021/ol101914f)
• 10b. K. Miki, M. Fujita, Y. Inoue, Y. Senda, T. Kowada, K. Ohe. J. Org. Chem. 75, 3537 (2010). (http://dx.doi.org/10.1021/jo1006202)
• 10c. A. Dell’Aquila, F. Marinelli, J. Tey, P. Keg, Y.-M. Lam, O. L. Kapitanchuk, P. Mastrorilli, C. F. Nobile, P. Cosma, A. Marchenko, D. Fichou, S. G. Mhaisalkar, G. P. Suranna, L. Torsi. J. Mater. Chem. 18, 786 (2008). (http://dx.doi.org/10.1039/b714865h)
• 11. Selected examples of oligomers with other aromatic units.
• 11a. J. G. Rodriguez, J. L. Tejedor. J. Org. Chem. 67, 7631 (2002). (http://dx.doi.org/10.1021/jo0203589)
• 11b. G. Venkataramana, P. Dongare, L. N. Dawe, D. W. Thompson, Y. Zhao, G. J. Bodwell. Org. Lett. 13, 2240 (2011). (http://dx.doi.org/10.1021/ol200485x)
• 11c. D. Lehnherr, R. R. Tykwinski. Aust. J. Chem. 64, 919 (2011). (http://dx.doi.org/10.1071/CH11169)
• 12a. T. Makino, S. Toyota. Bull. Chem. Soc. Jpn. 78, 917 (2005). (http://dx.doi.org/10.1246/bcsj.78.917)
• 12b. S. Toyota, T. Yamamori, T. Makino. Tetrahedron 57, 3521 (2001). (http://dx.doi.org/10.1016/S0040-4020(01)00232-0)
• 12c. S. Toyota, T. Nakagawa, M. Kotani, M. ?ki, H. Uekusa, Y. Ohashi. Tetrahedron 58, 10345 (2002). (http://dx.doi.org/10.1016/S0040-4020(02)01408-4)
• 13. For a review, see: S. Toyota. Chem. Lett. 40, 12 (2011). (http://dx.doi.org/10.1246/cl.2011.12)
• 14a. H. E. Katz. J. Org. Chem. 54, 2179 (1989). (http://dx.doi.org/10.1021/jo00270a030)
• 14b. L. Flamigni, A. M. Talarico, B. Ventura, R. Rein, N. Solladié. Chem.—Eur. J. 12, 701 (2006). (http://dx.doi.org/10.1002/chem.200500789)
• 15a. R. Gleiter, R. Merger. In Modern Acetylene Chemistry, P. J. Stang, F. Diederich (Eds.), Chap. 8, VCH, Weinheim (1995).
• 15b. S. Eisler, R. McDonald, G. R. Loppnow, R. R. Tykwinski. J. Am. Chem. Soc. 122, 6917 (2000). (http://dx.doi.org/10.1021/ja000617g)
• 16. S. Toyota. Chem. Rev. 110, 5398 (2010). (http://dx.doi.org/10.1021/cr1000628)
• 17. M. Goichi, K. Segawa, S. Suzuki, S. Toyota. Synthesis 2116 (2005).
• 18a. S. Toyota, M. Goichi, M. Kotani. Angew. Chem., Int. Ed. 43, 2248 (2004). (http://dx.doi.org/10.1002/anie.200353647)
• 18b. S. Toyota, M. Goichi, M. Kotani, M. Takezaki. Bull. Chem. Soc. Jpn. 78, 2214 (2005). (http://dx.doi.org/10.1246/bcsj.78.2214)
• 19. S. Toyota, S. Suzuki, M. Goichi. Chem.—Eur. J. 12, 2482 (2006). (http://dx.doi.org/10.1002/chem.200501111)
• 20. P. Kissel, F. Weibel, L. Federer, J. Sakamoto, A. D. Schlüter. Synlett 1793 (2008).
• 21. All chiral HPLC columns mentioned in this article were products of Daicel Chemical Industries with registered trademarks.
• 22a. S. Toyota, H. Miyahara, M. Goichi, S. Yamasaki, T. Iwanaga. Bull. Chem. Soc. Jpn. 82, 931 (2009). (http://dx.doi.org/10.1246/bcsj.82.931)
• 22b. M. Goichi, S. Yamasaki, H. Miyahara, K. Wakamatsu, H. Akashi, S. Toyota. Chem. Lett. 36, 404 (2007). (http://dx.doi.org/10.1246/cl.2007.404)
• 22c. M. Goichi, S. Toyota. Chem. Lett. 35, 684 (2006). (http://dx.doi.org/10.1246/cl.2006.684)
• 23a. T. Ishikawa, T. Shimasaki, H. Akashi, T. Iwanaga, S. Toyota, M. Yamasaki. Bull. Chem. Soc. Jpn. 83, 220 (2010). (http://dx.doi.org/10.1246/bcsj.20090270)
• 23b. T. Ishikawa, T. Shimasaki, H. Akashi, S. Toyota. Org. Lett. 10, 417 (2008). (http://dx.doi.org/10.1021/ol702783v)
• 24a. S. Toyota, H. Miyahara, M. Goichi, K. Wakamatsu, T. Iwanaga. Bull. Chem. Soc. Jpn. 81, 1147 (2008). (http://dx.doi.org/10.1246/bcsj.81.1147)
• 24b. M. Goichi, H. Miyahara, S. Toyota. Chem. Lett. 35, 920 (2006). (http://dx.doi.org/10.1246/cl.2006.920)
• 25. S. Akiyama, S. Misumi, M. Nakagawa. Bull. Chem. Soc. Jpn. 33, 1293 (1960). (http://dx.doi.org/10.1246/bcsj.33.1293)
• 26. Recent reports on derivatives of 16 as electronic devices.
• 26a. W. Zhao, Q. Tang, H. S. Chan, J. Xu, K. Y. Lo, Q. Miao. Chem. Commun. 4324 (2008). (http://dx.doi.org/10.1039/b806601a)
• 26b. J. M. W. Chan, J. R. Tischler, S. E. Kooi, V. Bulovi?, T. M. Swager. J. Am. Chem. Soc. 131, 5659 (2009). (http://dx.doi.org/10.1021/ja900382r)
• 27. S. Toyota, M. Kurokawa, M. Araki, K. Nakamura, T. Iwanaga. Org. Lett. 9, 3655 (2007). (http://dx.doi.org/10.1021/ol701541q)
• 28. T. Iwanaga, K. Miyamoto, K. Tahara, K. Inukai, S. Okuhata, Y. Tobe, S. Toyota. Chem.—Asian J. In press. (http://dx.doi.org/10.1002/asia.201101000>)
• 29. S. Toyota, H. Onishi, Y. Kawai, T. Morimoto, H. Miyahara, T. Iwanaga, K. Wakamatsu. Org. Lett. 11, 321 (2009). (http://dx.doi.org/10.1021/ol802488z)
• 30. S. Toyota, H. Onishi, K. Wakamatsu, T. Iwanaga. Chem. Lett. 38, 350 (2009). (http://dx.doi.org/10.1246/cl.2009.350)
• 31. S. Toyota, T. Kawakami, R. Shinnishi, R. Sugiki, S. Suzuki, T. Iwanaga. Org. Biomol. Chem. 8, 4997 (2010). (http://dx.doi.org/10.1039/c0ob00290a)
• 32. S. Toyota, M. Yoshikawa, S. Imigi, K. Wakamatsu, T. Iwanaga. Unpublished results.
• 33. P. Kissel, J. van Heijst, R. Enning, A. Stemmer, A. D. Schlüter, J. Sakamoto. Org. Lett. 12, 2778 (2010). (http://dx.doi.org/10.1021/ol100877g)
• 34. S. Toyota, H. Harada, H. Miyahara, T. Kawakami, K. Wakamatsu, T. Iwanaga. Bull. Chem. Soc. Jpn. 84, 829 (2011). (http://dx.doi.org/10.1246/bcsj.20110121)
• 35. T. Ishikawa, T. Iwanaga, S. Toyota, M. Yamasaki. Bull. Chem. Soc. Jpn. 84, 729 (2011). (http://dx.doi.org/10.1246/bcsj.20110066)
• 36. S. Toyota, M. Kuga, A. Takatsu, M. Goichi, T. Iwanaga. Chem. Commun. 1323 (2008). (http://dx.doi.org/10.1039/b717496a)