196
N. Tohnai
10.6 Conclusion
In summary, a supramolecular-based hierarchical strategy was employed to build
a new class of porous structures with diamondoid networks, termed diamondoid
porous organic salts. Sterically hindered tetrahedral clusters prevent the excessive
interpenetration of the diamondoid network and produce a porous structure. In addition, these diamondoid networks are easily adjusted by changing the sulfonic acid
derivative, allowing control of the degree of interpenetration and number of voids.
Moreover, the flexible accumulation of clusters provides flexibility and stability to
the diamondoid network. The proposed strategy makes it possible to build organic
porous structures with various functions. Tetrahedral clusters are evidently an excellent platform for arranging a wide range of organic molecules into tetrahedral shapes,
even when the organic molecules themselves do not have a tetrahedral structure. This
ability contributes to easy structural changes and functionalization of porous materials. As an example, the introduction of polycyclic aromatic groups into a porous
structure could result in fluorescence properties depending on the template molecule
employed. Furthermore, the porosity (size, shape, stability, etc.) of such materials can
be controlled by selecting specific combinations of the two components. The extension of this strategy to other sulfonic acid derivatives has been actively investigated
in order to construct unique functional organic porous structures.
References
1. (a) Sozzani, P., Bracco, S., Comotti, A., Ferretti, L., Simonutti, R.:Angew. Chem. Int. Ed. 44,
1816−1820 (2005); (b) Mastalerz, M., Oppel, I.M.: Angew. Chem. Int. Ed. 51, 5252−5255
(2012); (c) Yang, W., Greenaway, A., Lin, X., Matsuda, R., Blake, A., Wilson, C., Lewis,
W., Hubberstey, P., Kitagawa, S., Champness, N., Schroder, M.: J. Am. Chem. Soc. 132,
14457−14469 (2010); (d) Sudik, A.C., Millward, A.R., Ockwig, N.W., Coté, A.P., Kim, J.,
Yaghi, O.M.: J. Am. Chem. Soc. 127, 7110−7118 (2005); (e) Furukawa, H., Yaghi, O.M.: J.
Am. Chem. Soc. 131, 8875−8883 (2009); (f) Tsue, H., Ishibashi, K., Tokita, S., Takahashi, H.,
Matsui, K., Tamura, R.: Chem. Eur. J. 14, 6125−6134 (2008)
2. (a) Lu, Z.Z., Zhang, R., Li, Y.Z., Guo, Z.J., Zheng, H. G.: J. Am.Chem. Soc. 133, 4172−4174
(2011); (b) Takashima, Y., Martinez, V.M., Furukawa, S., Kondo, M., Shimomura, S., Uehara,
H., Nakahama, M., Sugimoto, K., Kitagawa, S.: Nat. Commun., 2−8 (2011); (c) Yanai, N.,
Kitayama, K., Hijikata, Y., Sato, H., Matsuda, R., Kubota, Y., Takata, M., Mizuno, M., Uemura,
T., Kitagawa, S.: Nat. Mater. 10, 787−793 (2011)ss
3. (a) Yaghi, O.M., O’Keeffe, M., Ockwing, N.W., Chae, H.K., Eddaoudi, M., Kim, J.: Nature
423, 705−714 (2003); (b) Horike, S., Shimomura, S., Kitagawa, S.: Nat. Chem. 1, 695−704
(2009); (c) Farha, O.K., Hupp, J.T.: Acc. Chem. Res. 43, 1166−1175 (2010)
4. (a) Coté, A.P., Benin, A.I., Ockwig, N.W., Matzger, A.J., O’Keeffe, M., Yaghi, O.M.: Science
310, 1166−1170 (2005); (b) El-Kaderi, H.M., Hunt, J.R., Mendoza-Cortés, J.L., Côté, A.P.,
Taylor, R.E., O’Keeffe, M., Yaghi, O.M.: Science 316, 268−272 (2007)
5. (a) Holst, J.R., Trewin, A., Cooper, A.I.: Nat. Chem. 2, 915−920 (2010); (b) Tian, J.,
Thallapally, P.K., McGrail, B.P.: Cryst. Eng. Commun. 14, 1909−1919 (2012)
6. (a) Su, X., Guo, D.S., Liu, Y.: Cryst. Eng. Commun. 12, 947−952 (2010); (b) Leverd, P.C.,
Berthault, P., Lance, M., Nierlich, M.: Eur. J. Org. Chem., 133−139 (2000)
N. Tohnai
10.6 Conclusion
In summary, a supramolecular-based hierarchical strategy was employed to build
a new class of porous structures with diamondoid networks, termed diamondoid
porous organic salts. Sterically hindered tetrahedral clusters prevent the excessive
interpenetration of the diamondoid network and produce a porous structure. In addition, these diamondoid networks are easily adjusted by changing the sulfonic acid
derivative, allowing control of the degree of interpenetration and number of voids.
Moreover, the flexible accumulation of clusters provides flexibility and stability to
the diamondoid network. The proposed strategy makes it possible to build organic
porous structures with various functions. Tetrahedral clusters are evidently an excellent platform for arranging a wide range of organic molecules into tetrahedral shapes,
even when the organic molecules themselves do not have a tetrahedral structure. This
ability contributes to easy structural changes and functionalization of porous materials. As an example, the introduction of polycyclic aromatic groups into a porous
structure could result in fluorescence properties depending on the template molecule
employed. Furthermore, the porosity (size, shape, stability, etc.) of such materials can
be controlled by selecting specific combinations of the two components. The extension of this strategy to other sulfonic acid derivatives has been actively investigated
in order to construct unique functional organic porous structures.
References
1. (a) Sozzani, P., Bracco, S., Comotti, A., Ferretti, L., Simonutti, R.:Angew. Chem. Int. Ed. 44,
1816−1820 (2005); (b) Mastalerz, M., Oppel, I.M.: Angew. Chem. Int. Ed. 51, 5252−5255
(2012); (c) Yang, W., Greenaway, A., Lin, X., Matsuda, R., Blake, A., Wilson, C., Lewis,
W., Hubberstey, P., Kitagawa, S., Champness, N., Schroder, M.: J. Am. Chem. Soc. 132,
14457−14469 (2010); (d) Sudik, A.C., Millward, A.R., Ockwig, N.W., Coté, A.P., Kim, J.,
Yaghi, O.M.: J. Am. Chem. Soc. 127, 7110−7118 (2005); (e) Furukawa, H., Yaghi, O.M.: J.
Am. Chem. Soc. 131, 8875−8883 (2009); (f) Tsue, H., Ishibashi, K., Tokita, S., Takahashi, H.,
Matsui, K., Tamura, R.: Chem. Eur. J. 14, 6125−6134 (2008)
2. (a) Lu, Z.Z., Zhang, R., Li, Y.Z., Guo, Z.J., Zheng, H. G.: J. Am.Chem. Soc. 133, 4172−4174
(2011); (b) Takashima, Y., Martinez, V.M., Furukawa, S., Kondo, M., Shimomura, S., Uehara,
H., Nakahama, M., Sugimoto, K., Kitagawa, S.: Nat. Commun., 2−8 (2011); (c) Yanai, N.,
Kitayama, K., Hijikata, Y., Sato, H., Matsuda, R., Kubota, Y., Takata, M., Mizuno, M., Uemura,
T., Kitagawa, S.: Nat. Mater. 10, 787−793 (2011)ss
3. (a) Yaghi, O.M., O’Keeffe, M., Ockwing, N.W., Chae, H.K., Eddaoudi, M., Kim, J.: Nature
423, 705−714 (2003); (b) Horike, S., Shimomura, S., Kitagawa, S.: Nat. Chem. 1, 695−704
(2009); (c) Farha, O.K., Hupp, J.T.: Acc. Chem. Res. 43, 1166−1175 (2010)
4. (a) Coté, A.P., Benin, A.I., Ockwig, N.W., Matzger, A.J., O’Keeffe, M., Yaghi, O.M.: Science
310, 1166−1170 (2005); (b) El-Kaderi, H.M., Hunt, J.R., Mendoza-Cortés, J.L., Côté, A.P.,
Taylor, R.E., O’Keeffe, M., Yaghi, O.M.: Science 316, 268−272 (2007)
5. (a) Holst, J.R., Trewin, A., Cooper, A.I.: Nat. Chem. 2, 915−920 (2010); (b) Tian, J.,
Thallapally, P.K., McGrail, B.P.: Cryst. Eng. Commun. 14, 1909−1919 (2012)
6. (a) Su, X., Guo, D.S., Liu, Y.: Cryst. Eng. Commun. 12, 947−952 (2010); (b) Leverd, P.C.,
Berthault, P., Lance, M., Nierlich, M.: Eur. J. Org. Chem., 133−139 (2000)