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Spectral Study on Selective Encapsulation and Complexation of Chloroform by Cryptophane-E-(OEt)6
Corresponding Author(s) : C. Tao
Asian Journal of Chemistry,
Vol. 27 No. 4 (2015): Vol 27 Issue 4
Abstract
Cryptophane-E-(OEt)6 was synthesized and investigated the interaction with chloroform by fluorescence spectroscopy. The results indicate that cryptophane-E-(OEt)6 is able to selectively encapsulate chloroform. The variation of the fluorescence spectra in binary solvents with the increasing chloroform ratio suggests that cryptophane-E-(OEt)6 and chloroform can form a 1:1 complex and the binding constant is estimated to be 235 M-1, which is much smaller than the binding constant of cryptophane-E to chloroform. Without appreciable consequences on the cavity dimensions, the replacement of methoxy group in cryptophane-E by ethoxy substituents restricts the cross section of the host windows. This is mostly due to steric constraint of the larger ethoxy substituent.
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- A. Bouchet, T. Brotin, D. Cavagnat and T. Buffeteau, Chem. Eur. J., 16, 4507 (2010); doi:10.1002/chem.200902740.
- L. Laureano-Perez, R. Collé, D.R. Jacobson, R. Fitzgerald, N.S. Khan and I.J. Dmochowski, Appl. Radiat. Isot., 70, 1997 (2012); doi:10.1016/j.apradiso.2012.02.099.
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- J. Canceill, L. Lacombe and A. Collet, J. Am. Chem. Soc., 108, 4230 (1986); doi:10.1021/ja00274a067.
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- Y. Shi, X. Li, J. Yang, F. Gao and C. Tao, J. Fluoresc., 21, 531 (2011); doi:10.1007/s10895-010-0739-5.
- Z. Takacs, M. Soltésová, D. Kotsyubynskyy, J. Kowalewski, J. Lang, T. Brotin and J.-P. Dutasta, Magn. Reson. Chem., 48, 623 (2010); doi:10.1002/mrc.2637.
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References
A. Bouchet, T. Brotin, D. Cavagnat and T. Buffeteau, Chem. Eur. J., 16, 4507 (2010); doi:10.1002/chem.200902740.
L. Laureano-Perez, R. Collé, D.R. Jacobson, R. Fitzgerald, N.S. Khan and I.J. Dmochowski, Appl. Radiat. Isot., 70, 1997 (2012); doi:10.1016/j.apradiso.2012.02.099.
A. Bouchet, T. Brotin, M. Linares, H. Ågren, D. Cavagnat and T. Buffeteau, J. Org. Chem., 76, 4178 (2011); doi:10.1021/jo200519r.
J. Sloniec, M. Schnurr, C. Witte, U. Resch-Genger, L. Schröder and A. Hennig, Chem. Eur. J., 19, 3110 (2013); doi:10.1002/chem.201203773.
A. Bouchet, T. Brotin, M. Linares, H. Ågren, D. Cavagnat and T. Buffeteau, J. Org. Chem., 76, 1372 (2011); doi:10.1021/jo102350g.
O. Taratula, M.P. Kim, Y. Bai, J.P. Philbin, B.A. Riggle, D.N. Haase and I.J. Dmochowski, Org. Lett., 14, 3580 (2012); doi:10.1021/ol300943w.
C. Schmuck, Angew. Chem. Int. Ed., 46, 5830 (2007); doi:10.1002/anie.200702125.
J.J. Rebek, Angew. Chem. Int. Ed., 44, 2068 (2005); doi:10.1002/anie.200462839.
T. Brotin and J.P. Dutasta, Chem. Rev., 109, 88 (2009); doi:10.1021/cr0680437.
M.P. Schramm, P. Restorp, F. Zelder and J. Rebek, J. Am. Chem. Soc., 130, 2450 (2008); doi:10.1021/ja076162d.
R.M. Fairchild, A.I. Joseph, K.T. Holman, H.A. Fogarty, T. Brotin, J.-P. Dutasta, C. Boutin, G. Huber and P. Berthault, J. Am. Chem. Soc., 132, 15505 (2010); doi:10.1021/ja1071515.
K.E. Chaffee, H.A. Fogarty, T. Brotin, B.M. Goodson and J.P. Dutasta, J. Phys. Chem. A, 113, 13675 (2009); doi:10.1021/jp903452k.
C.-H. Zhang, W.-L. Shen, G.-M. Wen, J.-B. Chao, L.-P. Qin, S.-M. Shuang, C. Dong and M.M.F. Choi, Talanta, 76, 235 (2008); doi:10.1016/j.talanta.2007.11.047.
L. Garel, J.-P. Dutasta and A. Collet, Angew. Chem. Int. Ed. Engl., 32, 1169 (1993); doi:10.1002/anie.199311691.
J. Canceill, L. Lacombe and A. Collet, J. Am. Chem. Soc., 108, 4230 (1986); doi:10.1021/ja00274a067.
J. Canceill, M. Cesario, A. Collet, J. Guilhem, L. Lacombe, B. Lozach and C. Pascard, Angew. Chem. Int. Ed. Engl., 28, 1246 (1989); doi:10.1002/anie.198912461.
G.Z. Guangqin Zhu, X.L. Xueming Li, C.T. Chuanyi Tao, J.H. Jing Huang and J.Y. Jianchun Yang, Chin. Opt. Lett., 10, 100601 (2012); doi:10.3788/COL201210.100601.
Z. Takacs, M. Soltesova, J. Kowalewski, J. Lang, T. Brotin and J.-P. Dutasta, Magn. Reson. Chem., 51, 19 (2013); doi:10.1002/mrc.3898.
Z. Takacs, T. Brotin, J.-P. Dutasta, J. Lang, G. Todde and J. Kowalewski, J. Phys. Chem. B, 116, 7898 (2012); doi:10.1021/jp303469x.
M.A. Little, J. Donkin, J. Fisher, M.A. Halcrow, J. Loder and M.J. Hardie, Angew. Chem. Int. Ed., 51, 764 (2012); doi:10.1002/anie.201106512.
C. Garcia, D. Humilire, N. Riva, A. Collet and J.-P. Dutasta, Org. Biomol. Chem., 1, 2207 (2003); doi:10.1039/b211363e.
C.-H. Zhang, W.-L. Shen, R.-Y. Fan, G.-M. Zhang, S.-M. Shuang, C. Dong and M.M.F. Choi, Spectrochim. Acta A, 75, 157 (2010); doi:10.1016/j.saa.2009.10.004.
Y. Shi, X. Li, J. Yang, F. Gao and C. Tao, J. Fluoresc., 21, 531 (2011); doi:10.1007/s10895-010-0739-5.
Z. Takacs, M. Soltésová, D. Kotsyubynskyy, J. Kowalewski, J. Lang, T. Brotin and J.-P. Dutasta, Magn. Reson. Chem., 48, 623 (2010); doi:10.1002/mrc.2637.
C. Zhang, W. Shen, R. Fan, G. Zhang, L. Shangguan, J. Chao, S. Shuang, C. Dong and M.M.F. Choi, Anal. Chim. Acta, 650, 118 (2009); doi:10.1016/j.aca.2009.02.046.
T. Traoré, L. Delacour, S. Garcia-Argote, P. Berthault, J.-C. Cintrat and B. Rousseau, Org. Lett., 12, 960 (2010); doi:10.1021/ol902952h.
J. Canceill and A. Collet, J. Chem. Soc. Chem. Commun., 9, 582 (1988); doi:10.1039/c39880000582.
M. Lukeman, D. Veale, P. Wan, V.R.N. Munasinghe and J.E.T. Corrie, Can. J. Chem., 82, 240 (2004); doi:10.1139/v03-184.
M. Maus, W. Rettig, D. Bonafoux and R. Lapouyade, J. Phys. Chem. A, 103, 3388 (1999); doi:10.1021/jp9905023.
P.B. Kandagal, S. Ashoka, J. Seetharamappa, S.M.T. Shaikh, Y. Jadegoud and O.B. Ijare, J. Pharm. Biomed. Anal., 41, 393 (2006); doi:10.1016/j.jpba.2005.11.037.
Hyperchem 8.0 Package, Hypercube, Inc. 1115 NW 4th St. Gainesville, FL 32608, USA.
S. Mecozzi and J. Rebek Jr, Chem. Eur. J., 4, 1016 (1998); doi:10.1002/(SICI)1521-3765(19980615)4:6<1016::AID-CHEM1016>3.0.CO;2-B.
A. Varnek, S. Helissen, G. Wipff and A. Collet, J. Comput. Chem., 19, 820 (1998); doi:10.1002/(SICI)1096-987X(199806)19:8<820::AID-JCC2>3.0.CO;2-R.