Abstract
Two tetrasubsituted derivatives of tetramercaptothiacalix[4]arene in 1,3-alternate conformation bearing either four (3-cyano)propyl (1) or (4-cyano)benzyl (2) moieties have been synthesized and characterized in solution as well as in the solid state by X-ray diffraction on single crystals. Their propensity to form coordination networks was investigated in the presence of silver cation as connecting metal and hexafluorophosphate as counter ion. Whereas the combination of AgPF6 and 1 bearing four (3-cyano)propyl groups leads to a 1D silver coordination network, for 2, containing four (4-cyano)benzyl units, a 3D diamond-like architecture is obtained.
Similar content being viewed by others
References
B. F. Abrahams, B. F. Hoskins, R. Robson, J. Am. Chem. Soc., 1991, 113, 3606
S. R. Batten, R. Robson, Angew. Chem., Int. Ed., 1998, 37, 1460.
M. W. Hosseini, CrystEngComm., 2004, 6, 318.
A. J. Blake, N. R. Champness, P. Hubberstey, W.-S. Li, M. A. Withersby, M. Schröder, Coord. Chem. Rev., 1999, 193, 117
B. Moulton, M. J. Zaworotko, Chem. Rev., 2001, 101, 1629
M. Eddaoudi, D. B. Moler, H. Li, B. Chen, T. M. Reineke, M. O´Keeffe, O. M. Yaghi, Acc. Chem. Res., 2001, 34, 319
C. Janiak, Dalton Trans., 2003, 2781
L. Carlucci, G. Ciani, D. M. Proserpio, Coord. Chem. Rev., 2003, 246, 247
S. Kitagawa, R. Kitaura, S. Noro, Angew. Chem,. Int. Ed., 2004, 43, 2334
G. Férey, C. Mellot-Draznieks, C. Serre, F. Millange, Acc. Chem. Res., 2005, 38, 218
D. Bradshaw, J. B. Claridge, E. J. Cussen, T. J. Prior, M. J. Rosseinsky, Acc. Chem. Res., 2005, 38, 273
S. Kitagawa, K. Uemura, Chem. Soc. Rev., 2005, 34, 109
D. Maspoch, D. Ruiz-Molina, J. Veciana, Chem. Soc. Rev., 2007, 36, 770
J. R. Long, O. M. Yaghi, Chem. Soc. Rev., 2009, 38, 1213
C. Janiak, J. L. Vieth, New J. Chem., 2010, 34, 2366
Chem. Soc. Rev., 2009, 38, themed issue on organometallic frameworks
W. L. Leong, J. J. Vittal, Chem. Rev., 2011, 111, 688
Chem. Rev., 2012, 112, themed issue on organometallic frameworks.
N. R. Champness, Dalton Trans., 2011, 40, 10311.
M. Simard, D. Su, J. D. Wuest, J. Am. Chem. Soc., 1991, 113, 4696
S. Mann, Nature, 1993, 365, 499
J. D. Wuest, Chem. Commun., 2005, 5830
M. W. Hosseini, Chem. Commun., 2005, 5825.
M. W. Hosseini, Acc. Chem. Res., 2005, 38, 313.
C. D. Gutsche, in Calixarenes Revised: Monographs in Supramolecular Chemistry, Vol. 6, The Royal Society of Chemistry, Cambridge, 1998
Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens, in Calixarenes 2001, Eds Z. Asfari, V. Böhmer, J. Harrowfield, J. Vicens, Kluwer Academic, Dordrecht, 2001
M. W. Hosseini, ACS Series, Eds G. J. Lumetta, R. D. Rogers, A. S. Gopalan, 2000, 557, 296
I. S. Antipin, A. I. Konovalov, Mendeleev Commun., 2008, 18, 229.
G. Mislin, E. Graf, M. W. Hosseini, A. De Cian, N. Kyritsakas, J. Fischer, Chem Commun., 1998, 2545.
H. Kumagai, M. Hasegawa, S. Miyanari, Y. Sugawa, Y. Sato, T. Hori, S. Ueda, H. Kamiyama, S. Miyano, Tetrahedron Lett., 1997, 38, 3971.
H. Akdas, L. Bringel, E. Graf, M. W. Hosseini, G. Mislin, J. Pansanel, A. De Cian, J. Fischer, Tetrahedron Lett., 1998, 39, 2311.
M. W. Hosseini, in Calixarenes 2001, EdsZ. Asfari, V. Böhmer, J. Harrowfield, J. Vicens, Kluwer Academic, Dordrecht, 2001, pp.110
T. Kajiwara, N. Iki, M. Yamashita, Coord. Chem. Rev. 2007, 251, 1734.
M. N. Kozlova, S. Ferlay, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, N. Kyritsakas, M. W. Hosseini, Dalton Trans., 2007, 5126.
H. Akdas, E. Graf, M. W. Hosseini, A. De Cian, J. M. Harrowfield, Chem. Commun., 2000, 2219.
A. Ovsyannikov, M. N. Lang, S. Ferlay, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, N. Kyritsakas, M. W. Hosseini, Dalton Trans., 2013, 42, 126
A. Ovsyannikov, S. Ferlay, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, N. Kyritsakas, M. W. Hosseini, Dalton Trans., 2013, 42, 9946.
M. N. Kozlova, S. Ferlay, N. Kyritsakas, M. W. Hosseini, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, Chem. Commun., 2009, 2514.
J. Sykora, M. Himl, I. Stobor, I. Cisarova, P. Lhotak, Tetrahedron, 2007, 63, 2244.
K. Kim, S. Park, K.-M. Park, S. S. Lee, Cryst. Growth Des., 2011, 11, 4059
S. P. Bew, A. D. Burrows, T. Duren, M. F. Mahon, P. Z. Moghadam, V. M. Sebestyen, S. Thurston, Chem. Commun., 2012, 48, 4824
Z. Zhang, A. Drapailo, Y. Matvieiev, L. Wojtas, M. J. Zaworotko, Chem. Commun., 2013, 49, 8353.
P. Rao, M. W. Hosseini, A. De Cian, J. Fischer, Chem. Commun., 1999, 2169
H. Akdas, E. Graf, M. W. Hosseini, A. de Cian, A. Bilyk, B. W. Skelton, G. A. Koutsantonis, I. Murray, J. M. Harrowfield, A. H. White, Chem. Commun., 2002, 1042.
A. Ovsyannikov, S. Ferlay, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, N. Kyritsakas, M. W. Hosseini, Inorg. Chem., 2013, 52, 6776
A. Ovsyannikov, S. Ferlay, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, N. Kyritsakas, M. W. Hosseini, Dalton., 2014, 43, 158
A. Ovsyannikov, S. Ferlay, S. E. Solovieva, I. S. Antipin, A. I. Konovalov, N. Kyritsakas, M. W. Hosseini, CrystEngComm., 2014, 16, 3765.
G. M. Sheldrick, Program for Crystal The structure of Solution, University of Göttingen, Göttingen, 1997.
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the materials of the XXVI International Chugaev Conference on Coordination Chemistry (October 6—10, 2014, Kazan).
Université de Strasbourg, Laboratoire de Tectonique Moléculaire, UMR-CNRS 7140, Institut Le Bel, 4 rue Blaise Pascal, 67070 Strasbourg, France.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1955—1962, August, 2015.
Rights and permissions
About this article
Cite this article
Ovsyannikov, A.S., Ferlay, S., Solovieva, S.E. et al. Molecular tectonics: silver coordination networks based on tetramercaptothiacalix[4]arene in 1,3-alternate conformation bearing four nitrile groups. Russ Chem Bull 64, 1955–1962 (2015). https://doi.org/10.1007/s11172-015-1099-8
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-015-1099-8