Pure Appl. Chem., 2011, Vol. 83, No. 1, pp. 189-199
http://dx.doi.org/10.1351/PAC-CON-10-09-34
Published online 2010-11-12
Charge-by-charge assemblies based on planar anion receptors*
References
- 1a. G. Tsoucaris (Ed.). Current Challenges on Large Supramolecular Assemblies, NATO Science Series, Kluwer, Dordrecht (1999).
- 1b. A. Ciferri (Ed.). Supramolecular Polymers, Marcel Dekker, New York (2000).
- 1c. F. Würthner (Ed.). Supramolecular Dye Chemistry, Topics in Current Chemistry, 258, p. 324, Springer-Verlag, Berlin (2005).
- 1d. J. L. Atwood, J. W. Steed (Eds.). Organic Nanostructures, Wiley-VCH, Weinheim (2007).
- 2a. T. Chem. Rev. 99, 2071 (1999). ( . http://dx.doi.org/10.1021/cr980032t)
- 2b. P. Angew. Chem., Int. Ed. 39, 3772 (2000). , W. Keim.
- 2c. H. Bull. Chem. Soc. Jpn. 79, 1665 (2006). ( . http://dx.doi.org/10.1246/bcsj.79.1665)
- 3a. K. Chem. Rev. 105, 4148 (2005). ( . http://dx.doi.org/10.1021/cr0400919)
- 3b. M. J. Am. Chem. Soc. 128, 5570 (2006). ( , T. Kagata, K. Hoshino, T. Mukai, H. Ohno, T. Kato. http://dx.doi.org/10.1021/ja0606935)
- 3c. P. H. J. J. Am. Chem. Soc. 129, 14042 (2007). ( , T. M. Swager. http://dx.doi.org/10.1021/ja075651a)
- 3d. T. J. Am. Chem. Soc. 129, 10662 (2007). ( , M. Yoshio, T. Mukai, H. Ohno, T. Kato. http://dx.doi.org/10.1021/ja0740418)
- 3e. K. Org. Lett. 9, 4271 (2007). ( , T. Yasuda, M. Yoshio, T. Kato. http://dx.doi.org/10.1021/ol701741e)
- 3f. H. J. Am. Chem. Soc. 130, 1759 (2008). ( , M. Yoshio, K. Hoshino, T. Mukai, H. Ohno, T. Kato. http://dx.doi.org/10.1021/ja0775220)
- 3g. M. J. Am. Chem. Soc. 130, 9648 (2008). ( , M.-W. Grinstaff. http://dx.doi.org/10.1021/ja803248q)
- 3h. Md.‑A. J. Am. Chem. Soc. 131, 17722 (2009). ( , J. Motoyanagi, Y. Yamamoto, T. Fukushima, J. Kim, K. Kato, M. Takata, A. Saeki, S. Seki, S. Tagawa, T. Aida. http://dx.doi.org/10.1021/ja905373d)
- 4. Selected books for anion binding.
- 4a. A. Bianchi, K. Bowman-James, E. García-España (Eds.). Supramolecular Chemistry of Anions, Wiley-VCH, New York (1997).
- 4b. R. P. Singh, B. A. Moyer (Eds.). Fundamentals and Applications of Anion Separations, Kluwer Academic/Plenum, New York (2004).
- 4c. I. Stibor (Ed.). Anion Sensing, Topics in Current Chemistry, 255, p. 238, Springer-Verlag, Berlin (2005).
- 4d. J. L. Sessler, P. A. Gale, W.-S. Cho. Anion Receptor Chemistry, Royal Society of Chemistry, Cambridge, UK (2006).
- 4e. R. Vilar (Ed.). Recognition of Anions, Structure and Bonding, Springer-Verlag, Berlin (2008).
- 5a. Y. Angew. Chem., Int. Ed. 47, 2649 (2008). ( , A. H. Flood. http://dx.doi.org/10.1002/anie.200704717)
- 5b. Y. J. Am. Chem. Soc. 130, 12111 (2008). ( , A. H. Flood. http://dx.doi.org/10.1021/ja803341y)
- 5c. Y. J. Am. Chem. Soc. 132, 12838 (2010). ( , A. H. Flood. http://dx.doi.org/10.1021/ja105793c)
- 6. H. Angew. Chem., Int. Ed. 47, 3740 (2008). ( , J. M. Lendhardt, D. M. Pham, S. L. Craig. http://dx.doi.org/10.1002/anie.200800548)
- 7a. K.-J. Angew. Chem., Int. Ed. 44, 7926 (2005). ( , D. Moon, M. S. Lah, K.-S. Jeong. http://dx.doi.org/10.1002/anie.200503121)
- 7b. K.-J. J. Am. Chem. Soc. 127, 12214 (2005). ( , B.-N. Kang, M.-H. Lee, K.-S. Jeong. http://dx.doi.org/10.1021/ja0547984)
- 7c. J.‑m. J. Am. Chem. Soc. 130, 11868 (2008). ( , S.-K. Jeong. http://dx.doi.org/10.1021/ja804845m)
- 7d. V. R. Org. Lett. 10, 5373 (2008). ( , M. C. Kim, J.-m. Suk, H.-J. Kim, M. Lee, E. Sim, K.-S. Jeong. http://dx.doi.org/10.1021/ol8022243)
- 7e. U.-I. Chem.—Eur. J. 14, 11406 (2008). ( , J.-m. Suk, V. R. Naidu, K.-S. Jeong. http://dx.doi.org/10.1002/chem.200801713)
- 7f. J.-i. Chem. Commun. 46, 764 (2010). ( , H. Juwarker, X. Liu, M. S. Lah, K.-S. Jeong. http://dx.doi.org/10.1039/b919519j)
- 8. G. W. Chem. Commun. 2121 (2007). ( , P. A. Gale, M. L. Light. http://dx.doi.org/10.1039/b703905k)
- 9. H. Fischer, H. Orth. Die Chemie des Pyrrols. Akademische Verlagsgesellschaft, Leipzig (1934).
- 10. K. M. Kadish K. M. Smith, R. Guilard (Eds.). The Porphyrin Handbook, Academic Press, San Diego (2000).
- 11. Some of the representative papers for calixpyrroles.
- 11a. P. A. J. Am. Chem. Soc. 118, 5140 (1996). ( , J. L. Sessler, V. Král, V. Lynch. http://dx.doi.org/10.1021/ja960307r)
- 11b. R. Angew. Chem., Int. Ed. 44, 2537 (2005). ( , L. H. Delmau, B. A. Moyer, J. L. Sessler, W.-S. Cho, D. Gross, G. W. Bates, S. J. Brooks, M. E. Light, P. A. Gale. http://dx.doi.org/10.1002/anie.200462945)
- 11c. J. L. J. Am. Chem. Soc. 128, 12281 (2006). ( , D. E. Gross, W.-S. Cho, V. M. Lynch, F. P. Schmidtchen, G. W. Bates, M. E. Light, P. A. Gale. http://dx.doi.org/10.1021/ja064012h)
- 12a. H. Eur. J. Org. Chem. 5313 (2007). ( . http://dx.doi.org/10.1002/ejoc.200700382)
- 12b. H. J. Incl. Phenom. 64, 193 (2009). .
- 12c. H. Maeda. In Handbook of Porphyrin Science, Vol. 8, K. M. Kadish K. M. Smith, R. Guilard (Eds.), Chap. 38, World Scientific, New Jersey (2010).
- 12d. H. Maeda. “Acyclic oligopyrrolic anion receptors”, in Anion Complexation in Supramolecular Chemistry, Topics in Heterocyclic Chemistry, P. A. Gale, W. Dehaen (Eds.), 24, p. 103, Springer-Verlag, Berlin (2010).
- 12e. H. Maeda. In Supramolecular Soft Matter: Applications in Materials and Organic Electronics, T. Nakanishi (Ed.), John Wiley. Submitted for publication.
- 13a. H. Chem.—Eur. J. 11, 5661 (2005). ( , Y. Kusunose. http://dx.doi.org/10.1002/chem.200500627)
- 13b. C. J. Org. Chem. 71, 2389 (2006). ( , Y. Kusunose, H. Maeda. http://dx.doi.org/10.1021/jo052511f)
- 13c. H. Inorg. Chem. 45, 8205 (2006). ( , Y. Ito. http://dx.doi.org/10.1021/ic0608703)
- 13d. H. J. Org. Chem. 72, 2612 (2007). ( , Y. Kusunose, Y. Mihashi, T. Mizoguchi. http://dx.doi.org/10.1021/jo062660d)
- 13e. H. Org. Biomol. Chem. 6, 433 (2008). ( , M. Terasaki, Y. Haketa, Y. Mihashi, Y. Kusunose. http://dx.doi.org/10.1039/b718317h)
- 13f. H. Synth. Met. 159, 792 (2009). ( , Y. Haketa, Y. Bando, S. Sakamoto. http://dx.doi.org/10.1016/j.synthmet.2009.01.004)
- 14a. H. J. Am. Chem. Soc. 129, 13661 (2007). ( , Y. Haketa, T. Nakanishi. http://dx.doi.org/10.1021/ja074435z)
- 14b. H. Org. Biomol. Chem. 6, 3091 (2008). ( , Y. Haketa. http://dx.doi.org/10.1039/b806161k)
- 14c. H. Org. Lett. 10, 3179 (2008). ( , Y. Mihashi, Y. Haketa. http://dx.doi.org/10.1021/ol801014z)
- 14d. H. Chem. Lett. 38, 208 (2009). ( , N. Eifuku. http://dx.doi.org/10.1246/cl.2009.208)
- 14e. H. Chem.—Eur. J. 15, 3709 (2009). , Y. Ito, Y. Haketa, N. Eifuku, E. Lee, M. Lee, T. Hashishin, K. Kaneko.
- 14f. H. Eur. J. Org. Chem. 1469 (2010). ( , R. Fujii, Y. Haketa. http://dx.doi.org/10.1002/ejoc.200901346)
- 14g. H. Chem. Commun. 46, 4559 (2010). ( , Y. Terashima, Y. Haketa, A. Asano, Y. Honsho, S. Seki, M. Shimizu, H. Mukai, K. Ohta. http://dx.doi.org/10.1039/c0cc00551g)
- 14h. H. Chem.—Eur. J. 16, 10994 (2010). ( , Y. Bando, Y. Haketa, Y. Honsho, S. Seki, H. Nakajima, N. Tohnai. http://dx.doi.org/10.1002/chem.201001852)
- 14i. Y. Haketa, H. Maeda. Chem.—Eur. J. In press (http://dx.doi.org/10.1002/chem.201002748)
- 14j. H. Maeda, N. Eifuku, Y. Haketa, Y. Ito, E. Lee, M. Lee. Submitted for publication.
- 14k. Y. Haketa, S. Sakamoto, T. Nakanishi, H. Maeda. In revision.
- 15a. H. Chem. Commun. 4285 (2008). ( , Y. Fujii, Y. Mihashi. http://dx.doi.org/10.1039/b806361c)
- 15b. H. Org. Biomol. Chem. 8, 4308 (2010). ( , M. Takayama, K. Kobayashi, H. Shinmori. http://dx.doi.org/10.1039/c0ob00044b)
- 16a. H. Chem. Asian J. 2, 350 (2007). ( , Y. Kusunose, M. Terasaki, Y. Ito, C. Fujimoto, R. Fujii, T. Nakanishi. http://dx.doi.org/10.1002/asia.200600379)
- 16b. H. Chem. Commun. 1136 (2007). ( , Y. Ito, Y. Kusunose, T. Nakanishi. http://dx.doi.org/10.1039/b615787d)
- 16c. H. Chem. Commun. 2726 (2007). ( , M. Hasegawa, A. Ueda. http://dx.doi.org/10.1039/b703236f)
- 16d. Y. Haketa, N. Eifuku, Y. Bando, I. Yamada, A. Hagihara, H. Maeda. Supramol. Chem. In press (http://dx.doi.org/10.1080/10610278.2010.521834)
- 17. Recent reviews of anion-responsive supramolecular gels.
- 17a. H. Chem.—Eur. J. 14, 11274 (2008). ( . http://dx.doi.org/10.1002/chem.200801333)
- 17b. G. O. Nat. Chem. 1, 437 (2009). ( , J. W. Steed. http://dx.doi.org/10.1038/nchem.283)
- 17c. M.-O. M. Chem. Rev. 110, 1960 (2010). ( , G. O. Lloyd, N. Clarke, J. W. Steed. http://dx.doi.org/10.1021/cr9003067)
- 18. Single-crystal structures of 12a, 12b, and 12c with TPACl revealed the formation of [1 + 1]-, [2 + 2]-, and [1 + 2]-type helical structures, respectively, which are assembled to TPA cations and provide charge-by-charge assemblies in the solid state. See ref. [14i].
- 19a. Y. Science 314, 1761 (2006). ( , T. Fukushima, Y. Suna, N. Ishii, A. Saeki, S. Seki, S. Tagawa, M. Taniguchi, T. Kawai, T. Aida. http://dx.doi.org/10.1126/science.1134441)
- 19b. Y. Proc. Natl. Acad. Sci. USA 106, 21051 (2009). ( , G. Zhang, W. Jin, T. Fukushima, T. Minari, N. Ishii, A. Saeki, S. Seki, S. Tagawa, T. Minari, K. Tsukagoshi, T. Aida. http://dx.doi.org/10.1073/pnas.0905655106)
- 19c. T. Adv. Mater. 22 1767 (2010). ( , N. Tezuka, S. Seki, Y. Matano, M. Nishi, K. Hirao, H. Lehtivuori, V. N. Tkachenko, H. Lemmetyinen, Y. Nakao, S. Sakaki, H. Imahori. http://dx.doi.org/10.1002/adma.200903056)
- 20. Soft materials, such as supramolecular gels and thermotropic liquid crystals, based on charge-by-charge assemblies can be fabricated from receptor molecules bearing aliphatic chains by complexation with anions as π-conjugated planar cation salts instead of tetraalkylammonium salts. As references for 6a_TPACl and 6a_TPABr, single-crystal structures of 6a with Cl– and Br– as planar cation salts also elucidated solid-state charge-by-charge assemblies comprising alternatively stacking planar receptor–anion complexes (6a_Cl– and 6a_Br–) and planar cations. Y. Haketa, S. Sasaki, N. Ohta, H. Masunaga, H. Ogawa, F. Araoka, H. Takezoe, H. Maeda. Angew. Chem., Int. Ed. In press (http://dx.doi.org/10.1002/anie.201006356)