Abstract
This review discusses the creation of aromatic folded structures in a zigzag way in crystalline state. A pillar-like columnar array of aromatic rings by folding can be constructed by using U-shaped linkers to connect the aromatic rings. As such linkers, ureylene and iminodicarbonyl groups have been utilized. Physical and spectroscopic properties of aromatic foldamers created in this fashion are affected considerably with increasing numbers of aromatic rings involved. To create folding networks by hydrogen bonding in crystal structures, U-shaped urea building blocks were developed. A variety of folded structures have been generated in the cocrystals by hydrogen bonding between the building blocks and hydrogen-bonding acceptor molecules. Interesting examples of stacked zigzag ribbon-type aromatic folding architectures are also presented.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
D.H. Appella, L.A. Christianson, I.L. Karle, D.R. Powell, S.H. Gellman, J. Am. Chem. Soc. 118, 13071–13072 (1996)
S.H. Gellman, Acc. Chem. Res. 31, 173–180 (1998)
C.M. Goodman, S. Choi, W.F. DeGrado, Nat. Chem. Biol. 3, 252–262 (2007)
G. Guichard, I. Huc, Chem. Commun. 47, 5933–5941 (2011)
D.J. Hill, M.J. Mio, R.B. Prince, T.S. Hughes, J.S. Moore, Chem. Soc. Rev. 101, 3893–4011 (2001)
L. Sebaoun, V. Marizot, T. Granier, B. Kauffmann, I. Huc, J. Am. Chem. Soc. 136, 2168–2174 (2014)
D.-W. Zhang, X. Zhao, J.-L. Hou, Z.-T. Li, Chem. Rev. 112, 5271–5316 (2012)
I. Huc, Eur. J. Org. Chem., 17–29 (2004)
J.C. Nelson, J.G. Saven, J.S. Moore, P.G. Wolynes, Science 277, 1793–1796 (1997)
M.T. Stone, J.M. Heemstra, J.S. Moore, Acc. Chem. Res. 39, 11–20 (2006)
A. Khan, C. Kaiser, S. Hecht, Angew. Chem. Int. Ed. 45, 1878–1881 (2006)
R.A. Smaldone, J.S. Moore, Chem. Eur. J. 14, 2650–2657 (2008)
K. Yamaguchi, G. Matsumura, H. Kagechika, I. Azumaya, Y. Ito, A. Itai, K. Shudo, J. Am. Chem. Soc. 113, 5474–5475 (1991)
A. Tanatani, H. Kagechika, I. Azumaya, K. Yamaguchi, K. Shudo, Chem. Pharm. Bull. 44, 1135–1137 (1996)
H. Masu, M. Sakai, K. Kishikawa, M. Yamamoto, K. Yamaguchi, S. Kohmoto, J. Org. Chem. 70, 1423–1431 (2005)
P. Gains, G. Avitabile, E. Benedetti, C. Pedone, M. Goodman, Proc. Natl. Acad. Sci. 67, 426–433 (1970)
G. Lepore, S. Migdal, D.E. Blagdon, M. Goodman, J. Org. Chem. 38, 2590–2594 (1973)
J. Clayden, U. Hennecke, M.A. Vincent, I.H. Hikkier, M. Helliwell, Phys. Chem. Chem. Phys. 12, 15056–15064 (2010)
E.A. Chandross, C.J. Dempster, J. Am. Chem. Soc. 92, 3586–3593 (1970)
T. Hayashi, N. Mataga, Y. Sakata, S. Misumi, M. Morita, J. Tanaka, J. Am. Chem. Soc. 98, 5910–5913 (1976)
A. Tsuchida, T. Ikawa, T. Tomie, M. Yamamoto, J. Phys. Chem. 99, 8169–8199 (1995)
F.D. Lewis, T.L. Kurth, W. Liu, Photochem. Photobiol. Sci. 1, 30–37 (2002)
T.L. Kurth, F.F. Lewis, J. Am. Chem. Soc. 125, 13760–13767 (2003)
H.L. Ricks, L.S. Shimizu, M.D. Smith, U.H.F. Bunz, K.D. Shimizu, Tetrahedron Lett. 45, 3229–3232 (2004)
T. Hirano, T. Osaki, S. Fujii, D. Komatsu, I. Azumaya, A. Tanatani, H. Kagechika, Tetrahedron Lett. 50, 488–491 (2009)
F.C. Krebs, M. Jørgensen, J. Org. Chem. 67, 7511–7518 (2002)
F.D. Lewis, T.L. Kurth, G.B.D. Santos, J. Phys. Chem. B 109, 4893–4899 (2005)
F.D. Lewis, T.L. Kurth, C.M. Hattan, R.C. Reiter, C.D. Stevenson, Org. Lett. 6, 1605–1608 (2004)
T.A. Zeidan, Q. Wang, T. Fiebig, F.D. Lewis, J. Am. Chem. Soc. 129, 9848–9849 (2007)
A. Tanatani, H. Kagechika, I. Azumaya, R. Fukutomi, Y. Ito, K. Yamaguchi, K. Shudo, Tetrahedron Lett. 38, 4425–4428 (1997)
J. Clayden, L. Lemiégre, M. Helliwell, J. Org. Chem. 72, 2302–2308 (2007)
M. Kudo, T. Hanashima, A. Muranaka, H. Sato, M. Uchiyama, I. Azumaya, T. Hirano, H. Kagechika, A. Tanatani, J. Org. Chem. 74, 8154–8163 (2009)
J. Clayden, L. Lemiégre, G.A. Morris, M. Pickworth, T.J. Snape, L.H. Jones, J. Am. Chem. Soc. 130, 15193–15202 (2008)
S. Hisamatsu, H. Masu, I. Azumaya, M. Takahashi, K. Kishikawa, S. Kohmoto, Cryst. Growth Des. 11, 1453–1457 (2011)
P. Gilli, L. Pretto, V. Bertolasi, G. Gilli, Acc. Chem. Res. 42, 33–44 (2009)
S. Hisamatu, H. Masu, M. Takahashi, M. Kishikawa, S. Kohmot, (unpublished work)
R. Krämer, J.-M. Lehn, A. DeCian, J. Fischer, Angew. Chem. Int. Ed. Engl. 32, 703–706 (1993)
P. Dapporto, P. Paoli, S. Roelens, J. Org. Chem. 66, 4930–4933 (2001)
S. Hisamatsu, H. Masu, I. Azumaya, M. Takahashi, K. Kishikawa, S. Kohmoto, Cryst. Growth Des. 11, 5387 (2011)
S. Hisamatsu, H. Masu, M. Takahashi, K. Kishikawa, S. Kohmoto, Tetrahedron Lett. 53, 3903–3906 (2012)
N.N. Adarsh, D.K. Kumar, P. Dastidar, Tetrahedron 63, 7386–7396 (2007)
M.C. Etter, D.A Adsmond, J. Chem. Soc. Chem. Commun., 589–591 (1990)
S. Hisamatsu, H. Masu, M. Takahashi, K. Kishikawa, Cryst. Growth Des. 13, 2327–2334 (2013)
S. Kohmoto, S. Sekizawa, S. Hisamatsu, H. Masu, M. Takahashi, K. Kishikawa, Cryst. Growth Des. 14, 2209–2217 (2014)
N.E. Braml, A. Sattler, W. Schnick, Chem. Eur. J. 18, 1811–1819 (2012)
S. Kohmoto, H. Masu, C. Tatsuno, K. Kishikawa, M. Yamamoto, K. Yamaguchi, J. Chem. Soc. Perkin Trans. 1, 4464–4468 (2000)
S. Kohmoto, Y. Ono, H. Masu, K. Yamaguchi, K. Kishikawa, M. Yamamoto, Org. Lett. 3, 4153–4155 (2001)
H. Masu, K. Ohmori, K. Kishikawa, M. Yamamoto, K. Yamaguchi, S. Kohmoto, Bull. Chem. Soc. Jpn. 78, 1127–1131 (2005)
K. Kishikawa, Y. Miwa, T. Kurosaki, S. Kohmoto, M. Yamamoto, K. Yamaguchi, Chem. Mater. 13, 2468–2471 (2001)
H. Masu, K. Ohmori, K. Kishikawa, M. Yamamoto, K. Yamaguchi, S. Kohmoto, Anal. Sci. 21, x33–x34 (2005)
H. Masu, I. Mizutani, Y. Ono, K. Kishikawa, I. Azumaya, K. Yamaguchi, S. Kohmoto, Cryst. Growth Des. 6, 2086–2091 (2006)
H. Masu, I. Mizutani, T. Kato, I. Azumaya, K. Yamaguchi, K. Kishikawa, S. Kohmoto, J. Org. Chem. 71, 8037–8044 (2006)
G. Snatzke, Angew. Chem. Int. Ed. Engl. 18, 363–377 (1979)
F. Franceschi, M. Guardigli, E. Solari, C. Floriani, A. Chiesi-Villa, C. Rizzoli, Inorg. Chem. 36, 4099–4107 (1997)
M. Kimura, K. Sirasu, H. Okamoto, K. Satake, S. Morosawa, Tetrahedron Lett. 33, 697–6978 (1992)
S. Aravinda, N. Shamala, C. Das, A. Sriranjini, I.L. Karle, P. Balaram, J. Am. Chem. Soc. 125, 5308–5315 (2003)
(a) Y. Inai, Y. Ishida, K. Tagawa, A. Takasu, T. Hirabayashi, J. Am. Chem. Soc. 124, 2466–2473 (2002). (b) H. Fenniri, B.-L. Deng, A.E. Ribbe, J. Am. Chem. Soc. 124, 11064–11072 (2002)
H. Jiang, C. Dolain, J.-M. Léger, H. Gornitzka, I. Huc, J. Am. Chem. Soc. 126, 1034–1035 (2004)
A. Gättli, X. Daura, D. Seebach, W.F. van Gunstern, J. Am. Chem. Soc. 124, 12972–12978 (2002)
S. Kohmoto, H. Takeichi, K. Kishikawa, H. Masu, I. Azumaya, Tetrahedron Lett. 49, 1223–1227 (2008)
L. Sebaoun, B. Kauffmann, T. Delclos, V. Maurizot, I. Huc, Org. Lett. 16, 2326–2329 (2014)
S. Li, D.-X. Wang, M.-X. Wang, Tetrahedron Lett. 53, 6426–6429 (2012)
Y. Morisaki, T. Sawamura, T. Murakami, Y. Chujo, Org. Lett. 12, 3188–3191 (2010)
S. Toyota, M. Kug, A. Takatsu, M. Goichi, T. Iwanaga, Chem. Commun., 1323–1325 (2008)
W. Zhang, D. Horoszewski, J. Decatur, C. Nuckolls, J. Am. Chem. Soc. 125, 4870–4873 (2003)
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer Japan
About this chapter
Cite this chapter
Kohmoto, S. (2015). Construction of Aromatic Folding Architecture: Utilization of Ureylene and Iminodicarbonyl Linkers. In: Tamura, R., Miyata, M. (eds) Advances in Organic Crystal Chemistry. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55555-1_11
Download citation
DOI: https://doi.org/10.1007/978-4-431-55555-1_11
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-55554-4
Online ISBN: 978-4-431-55555-1
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)