Inorganic Chemistry
Article
(18) Babu, S. S.; Kartha, K. K.; Ajayaghosh, A. J. Phys. Chem. Lett.
2010, 1, 3413.
(19) Kuroiwa, K.; Shibata, T.; Takada, A.; Nemoto, N.; Kimizuka, N.
the intermolecular hydrogen-bonding interaction between
DMF and HCl to form the tetrahedral structure. Furthermore,
the camera in particular smartphones is capable of detecting
VGCl by use of the histogram of RGB within the Android and
iOS application. The present study is a rare example of the
application of a coordination polymer gel as a chemoprobe for
VGCl such as HCl, SOCl2, (COCl)2, and COCl2. These results
suggest that the filter paper coated with G1 may also lead to
useful applications in other vaporized chemical sensing
applications. The concepts employed in the present study
should open the door for a range of new sensors based on
responsive soft materials such as G1 described here.
J. Am. Chem. Soc. 2004, 126, 2016.
(20) Lee, H.; Jung, S. H.; Han, W. S.; Moon, J. H.; Kang, S.; Lee, J.
Y.; Jung, J. H.; Shinkai, S. Chem.Eur. J. 2011, 17, 2823.
(21) Yen, C.-W.; Chen, J.-D. Inorg. Chem. Commun. 2011, 14, 1212.
(22) Morris, P. J.; Martin, R. B. J. Am. Chem. Soc. 1970, 92, 1543.
(23) Fu, S.-J.; Cheng, C.-Y.; Lin, K.-J. Cryst. Growth Des. 2007, 7,
1381.
(24) Wu, H.; Liu, B.; Kou, F.; Jia, F.; Yuan, J.; Bai, Y. Z. Anorg. Allg.
Chem. 2012, 638, 122.
(25) Borah, M. J.; Singh, R. K. B.; Sinha, U. B.; Swu, T.; Borah, P. J. J.
Chem. Crystallogr. 2012, 42, 67.
(26) Perkins, D. F.; Lindoy, L. F.; McAuley, A.; Meehan, G. V.;
Turner, P. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 532.
(27) Atkinson, I. M.; Lindoy, L. F. Coord. Chem. Rev. 2000, 200, 207.
(28) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713.
(29) Mecca, T.; Messina, G. M. L.; Marletta, G.; Consolo, F. Chem.
Commun. 2013, 49, 2530.
ASSOCIATED CONTENT
* Supporting Information
X-ray crystallographic data of 3 and 4 in CIF format,
information on the gelation test, and spectroscopic data. This
material is available free of charge via the Internet at http://
■
S
(30) Aoki, M.; Nakashima, K.; Kawabata, H.; Tsutsui, S.; Shinkai, S. J.
Chem. Soc., Perkin Trans. 2 1993, 347.
(31) Aoki, M.; Murata, K.; Shinkai, S. Chem. Lett. 1991, 1715.
(32) Kim, K.; Park, S.; Park, K.-M.; Lee, S. S. Cryst. Growth Des. 2011,
11, 4059.
(33) Cai, X.; Wu, Y.; Wang, L.; Yan, N.; Liu, J.; Fang, X.; Fang, Y. Soft
Matter 2013, 5807.
(34) Bew, S. P.; Burrows, A. D.; Duren, T.; Mahon, M. F.;
Moghadam, P. Z.; Sebestyen, V. M.; Thurston, S. Chem. Commun.
2012, 48, 4824.
(35) Yamada, M.; Ootashiro, Y.; Kondo, Y.; Hamada, F. Tetrahedron
Lett. 2013, 54, 1510.
(36) Messina, M. T.; Metrangolo, P.; Pappalardo, S.; Parisi, M. F.;
Pilati, T.; Resnati, G. Chem.Eur. J. 2000, 6, 3495.
(37) Kim, S. K.; Lynch, V. M.; Young, N. J.; Hay, P. B.; Lee, C.-H.;
Kim, J. S.; Moyer, B. A.; Sessler, J. L. J. Am. Chem. Soc. 2012, 134,
20837.
AUTHOR INFORMATION
Corresponding Author
Notes
■
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
This work was supported by a grant from the NRF (Grant
2012002547) supported by the Ministry of Education, Science
and Technology, Korea. In addition, this work was partially
supported by a grant from the Next-Generation BioGreen 21
Program (SSAC, Grant PJ009041), Rural Development
Administration, Korea.
(38) Nakamura, R.; Ikeda, A.; Sarson, L. D.; Shinkai, S. Supramol.
Chem. 1998, 9, 25.
REFERENCES
■
(39) Ikeda, A.; Irisa, T.; Hamano, T.; Kitahashi, T.; Sasaki, Y.;
Hashizume, M.; Kikuchi, J.; Konishi, T.; Shinkai, S. Org. Biomol. Chem.
2006, 4, 519.
(40) Xing, B.; Choi, M.-F.; Xu, B. Chem.Eur. J. 2002, 8, 5028.
(41) Goh, C. Y.; Becker, T.; Brwon, D. H.; Skelton, B. W.; Jones, F.;
Mocerino, M.; Ogden, M. I. Chem. Commun. 2011, 47, 6057.
(42) Becker, T.; Goh, C. Y.; Jones, F.; McIldowie, M. J.; Mocerino,
M.; Ogden, M. I. Chem. Commun. 2008, 3900.
(1) Fages, F. Angew. Chem., Int. Ed. 2006, 45, 1680.
(2) Leong, W. L.; Tam, A. Y.-Y.; Batabyal, S. K.; Koh, L. W.; Kasapis,
S.; Yam, V. W.-W.; Vittal, J. J. Chem. Commun. 2008, 3628.
(3) Batabyal, S. K.; Leong, W. L.; Vittal, J. J. Langmuir 2010, 26,
7464.
(4) Leong, W. L.; Batabyal, S. K.; Kasapis, S.; Vittal, J. J. Chem.Eur.
J. 2008, 14, 8822.
(5) Paulusse, J. M. J.; van Beek, D. J. M.; Sijbesma, R. P. J. Am. Chem.
Soc. 2007, 129, 2392.
(6) Hui, J. K.-H.; Yu, Z.; MacLachlan, M. J. Angew. Chem., Int. Ed.
2007, 46, 7980.
(7) Weng, W.; Beck, J. B.; Jamieson, A. M.; Rowan, S. J. J. Am. Chem.
Soc. 2006, 128, 11663.
(8) Kim, H.-J.; Lee, J.-H.; Lee, M. 2005, 44, 5810.
(9) Lloyd, G. O.; Steed, J. W. Nat. Chem. 2009, 1, 437.
(10) Jung, J. H.; Lee, J.; Siverman, J. R.; John, G. Chem. Soc. Rev.
2013, 42, 924.
(43) Zhang, J.; Guo, D.-S.; Wang, L.-H.; Wang, Z.; Liu, Y. Soft Matter
2011, 7, 1756.
(44) Harrowfield, J.; Koutsantonis, G. Calixarenes as Cluster Keeper.
In Calixarenes in the Nanoworld; Vicens, J., Harrowfield, J., Eds.;
Springer: Dordrecht, The Netherlands, 2007; p 197.
(45) Morohashi, N.; Narumi, F.; Iki, N.; Hattori, T.; Miyano, S.
Chem. Rev. 2006, 106, 5291.
(46) Kajiwara, T.; Iki, N.; Yamashita, M. Coord. Chem. Rev. 2007,
251, 1734.
(47) Macias, A. T.; Norton, J. E.; Evanseck, J. D. J. Am. Chem. Soc.
2003, 125, 2351.
(11) Kartha, K. K.; Babu, S. S.; Srinivasan, S.; Ajayaghosh, A. J. Am.
Chem. Soc. 2012, 134, 4834.
(48) Praveen, L.; Ganga, V. B.; Thirumalai, R.; Sreeja, T.; Reddy, M.
L. P.; Luxmi Varma, R. Inorg. Chem. 2007, 46, 6277.
(49) Chen, T.; Chen, Q.; Zhang, X.; Wang, D.; Wan, L.-J. J. Am.
Chem. Soc. 2010, 132, 5598.
(50) Dai, F.-R.; Wang, Z. J. Am. Chem. Soc. 2012, 134, 8002.
(51) Liu, M.; Liao, W.; Hu, C.; Du, S.; Zhang, H. Angew. Chem., Int.
Ed. 2012, 51, 1585.
(52) Kumar, M.; Dhir, A.; Bhalla, V. Org. Lett. 2009, 11, 2567.
(53) Kumar, M.; Kumar, R.; Bhalla, V. Chem. Commun. 2009, 7384.
(54) Iki, N.; Morohashi, N.; Narumi, F.; Fujimoto, T.; Suzuki, T.;
Miyano, S. Tetrahedron Lett. 1999, 40, 7337.
(12) Sajisha, V. S.; Maitra, U. Chemia 2013, 67, 44.
(13) Lee, H.; Kang, S.; Lee, J. Y.; Jung, J. H. Soft Matter 2012, 8,
2950.
(14) Roubeau, O.; Colin, A.; Schmitt, V.; Clerac, R. Angew. Chem.,
Int. Ed. 2004, 43, 3283.
(15) Shirakawa, M.; Fujita, N.; Tani, T.; Kaneko, K.; Ojima, M.; Fujii,
A.; Ozaki, M.; Shinkai, S. Chem.Eur. J. 2007, 13, 4155.
(16) Piepenbrock, M.-O.; Clarke, N.; Steed, J. W. Langmuir 2009, 25,
8451.
(17) Babu, S. S.; Praveen, V. K.; Prasanthkumar, S.; Ajayaghosh, A.
Chem.Eur. J. 2008, 14, 9577.
3010
dx.doi.org/10.1021/ic402804p | Inorg. Chem. 2014, 53, 3004−3011