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Design and Synthesis of Novel Fluorescent Phthalimide Based Silatranes: Ratiometric Estimation of Mg2+ Ion
Corresponding Author(s) : Gurjaspreet Singh
Asian Journal of Chemistry,
Vol. 29 No. 9 (2017): Vol 29 Issue 9
Abstract
Organosilicon analogues of nitrogen-substituted phthalimide were synthesized and characterized by NMR (1H and 13C), ESI-MS and HRMS spectroscopic techniques. The recognition properties of fluorescent silatranes were studied and it was found that the structural variations play important role for metal recognition and one receptor has shown ratiometric estimation of Mg2+ over other tested metal ions.
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- R. Tacke, T. Heinrich, R. Bertermann, C. Burschka, A. Hamacher and M.U. Kassack, Organometallics, 23, 4468 (2004); https://doi.org/10.1021/om040067l.
- G. Singh, S.S. Mangat, H. Sharma, J. Singh, A. Arora, A.P. Singh Pannu and N. Singh, RSC Adv., 4, 36834 (2014); https://doi.org/10.1039/C4RA02270J.
- G. Singh, S.S. Mangat, J. Singh, A. Arora and M. Garg, J. Organomet. Chem., 769, 124 (2014); https://doi.org/10.1016/j.jorganchem.2014.07.014.
- G. Singh, A. Arora, S.S. Mangat, J. Singh, S. Chaudhary, N. Kaur and D. Choquesillo-Lazarte, J. Mol. Struct., 1079, 173 (2015); https://doi.org/10.1016/j.molstruc.2014.09.042.
- G. Singh, J. Singh, S.S. Mangat and A. Arora, RSC Adv., 4, 60853 (2014); https://doi.org/10.1039/C4RA08724K.
- G. Singh, J. Singh, S.S. Mangat and A. Arora, Tetrahedron Lett., 55, 2551 (2014); https://doi.org/10.1016/j.tetlet.2014.03.043.
- G. Singh, S.S. Mangat, J. Singh, A. Arora and R.K. Sharma, Tetrahedron Lett., 55, 903 (2014); https://doi.org/10.1016/j.tetlet.2013.12.037.
- J.K. Puri, R. Singh and V.K. Chahal, Chem. Soc. Rev., 40, 1791 (2011); https://doi.org/10.1039/B925899J.
- C. Sanchez, B. Julian, P. Belleville and M. Popall, J. Mater. Chem., 15, 3559 (2005); https://doi.org/10.1039/b509097k.
- M. Vallet-Regi, F. Balas and D. Arcos, Angew. Chem. Int. Ed., 46, 7548 (2007); https://doi.org/10.1002/anie.200604488.
- C.G. Allen, D.J. Baker, J.M. Albin, H.E. Oertli, D.T. Gillaspie, D.C. Olson, T.E. Furtak and R.T. Collins, Langmuir, 24, 13393 (2008); https://doi.org/10.1021/la802621n.
- J.A. Howarter and J.P. Youngblood, Langmuir, 22, 11142 (2006); https://doi.org/10.1021/la061240g.
- Z. Jin, X.B. Zhang, D.X. Xie, Y.J. Gong, J. Zhang, X. Chen, G.L. Shen and R.Q. Yu, Anal. Chem., 82, 6343 (2010); https://doi.org/10.1021/ac101305e.
- A. Zamboulis, N. Moitra, J.J.E. Moreau, X. Cattoën and M.W.C. Man, J. Mater. Chem., 20, 9322 (2010); https://doi.org/10.1039/c000334d.
- O. De Los Cobos, B. Fousseret, M. Lejeune, F. Rossignol, M. Dutreilh- Colas, C. Carrion, C. Boissière, F. Ribot, C. Sanchez, X. Cattoën, M.W.C. Man and J.-O. Durand, Chem. Mater., 24, 4337 (2012); https://doi.org/10.1021/cm3022769.
- N. Moitra, J.J.E. Moreau, X. Cattoën and M.W.C. Man, Chem. Commun., 46, 8416 (2010); https://doi.org/10.1039/c0cc03417g.
- V.A. Kuksa, V.A. Pavlov and P.K. Lin, Bioorg. Med. Chem. Lett., 10, 1265 (2000); https://doi.org/10.1016/S0960-894X(00)00201-8.
- N. Singh, R.C. Mulrooney, N. Kaur and J.F. Callan, Chem. Commun., 40, 4900 (2008); https://doi.org/10.1039/b813423e.
- H. Sharma, N. Kaur, T. Pandiyan and N. Singh, Sens. Actuators B Chem., 166-167, 467 (2012); https://doi.org/10.1016/j.snb.2012.01.076.
- K. Kaur, N. Kaur and N. Singh, Mater. Lett., 80, 78 (2012); https://doi.org/10.1016/j.matlet.2012.04.043.
- H. Sharma, K. Narang, N. Singh and N. Kaur, Mater. Lett., 84, 104 (2012); https://doi.org/10.1016/j.matlet.2012.06.066.
- A. Chandrasekaran, R.O. Day and R.R. Holmes, J. Am. Chem. Soc., 122, 1066 (2000); https://doi.org/10.1021/ja9926360.
- C. Lee, W. Yang and R.G. Parr, Phys. Rev. B, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785.
- A. Hartwig, Mutat. Res., 475, 113 (2001); https://doi.org/10.1016/S0027-5107(01)00074-4.
- M.L. Lima, T. Cruz, L.E. Rodrigues, O. Bomfim, J. Melo, R. Correia, M. Porto, A. Cedro and E. Vicente, Diabetes Res. Clin. Pract., 83, 257 (2009); https://doi.org/10.1016/j.diabres.2008.11.019.
- P. Bühlmann, E. Pretsch and E. Bakker, Chem. Rev., 98, 1593 (1998); https://doi.org/10.1021/cr970113+.
- G. Farruggia, S. Iotti, L. Prodi, M. Montalti, N. Zaccheroni, P.B. Savage, V. Trapani, P. Sale and F.I. Wolf, J. Am. Chem. Soc., 128, 344 (2006); https://doi.org/10.1021/ja056523u.
- Y. Liu, Z.-Y. Duan, H.-Y. Zhang, X.-L. Jiang and J.-R. Han, J. Org. Chem., 70, 1450 (2005); https://doi.org/10.1021/jo047968o.
- H. Hama, T. Morozumi and H. Nakamura, Tetrahedron Lett., 48, 1859 (2007); https://doi.org/10.1016/j.tetlet.2006.12.147.
- J.S. Yang, C.Y. Hwang and M.Y. Chen, Tetrahedron Lett., 48, 3097 (2007); https://doi.org/10.1016/j.tetlet.2007.02.120.
- E. Tomat and S. Lippard, J. Inorg. Chem., 49, 9113 (2010); https://doi.org/10.1021/ic101513a.
References
R. Tacke, T. Heinrich, R. Bertermann, C. Burschka, A. Hamacher and M.U. Kassack, Organometallics, 23, 4468 (2004); https://doi.org/10.1021/om040067l.
G. Singh, S.S. Mangat, H. Sharma, J. Singh, A. Arora, A.P. Singh Pannu and N. Singh, RSC Adv., 4, 36834 (2014); https://doi.org/10.1039/C4RA02270J.
G. Singh, S.S. Mangat, J. Singh, A. Arora and M. Garg, J. Organomet. Chem., 769, 124 (2014); https://doi.org/10.1016/j.jorganchem.2014.07.014.
G. Singh, A. Arora, S.S. Mangat, J. Singh, S. Chaudhary, N. Kaur and D. Choquesillo-Lazarte, J. Mol. Struct., 1079, 173 (2015); https://doi.org/10.1016/j.molstruc.2014.09.042.
G. Singh, J. Singh, S.S. Mangat and A. Arora, RSC Adv., 4, 60853 (2014); https://doi.org/10.1039/C4RA08724K.
G. Singh, J. Singh, S.S. Mangat and A. Arora, Tetrahedron Lett., 55, 2551 (2014); https://doi.org/10.1016/j.tetlet.2014.03.043.
G. Singh, S.S. Mangat, J. Singh, A. Arora and R.K. Sharma, Tetrahedron Lett., 55, 903 (2014); https://doi.org/10.1016/j.tetlet.2013.12.037.
J.K. Puri, R. Singh and V.K. Chahal, Chem. Soc. Rev., 40, 1791 (2011); https://doi.org/10.1039/B925899J.
C. Sanchez, B. Julian, P. Belleville and M. Popall, J. Mater. Chem., 15, 3559 (2005); https://doi.org/10.1039/b509097k.
M. Vallet-Regi, F. Balas and D. Arcos, Angew. Chem. Int. Ed., 46, 7548 (2007); https://doi.org/10.1002/anie.200604488.
C.G. Allen, D.J. Baker, J.M. Albin, H.E. Oertli, D.T. Gillaspie, D.C. Olson, T.E. Furtak and R.T. Collins, Langmuir, 24, 13393 (2008); https://doi.org/10.1021/la802621n.
J.A. Howarter and J.P. Youngblood, Langmuir, 22, 11142 (2006); https://doi.org/10.1021/la061240g.
Z. Jin, X.B. Zhang, D.X. Xie, Y.J. Gong, J. Zhang, X. Chen, G.L. Shen and R.Q. Yu, Anal. Chem., 82, 6343 (2010); https://doi.org/10.1021/ac101305e.
A. Zamboulis, N. Moitra, J.J.E. Moreau, X. Cattoën and M.W.C. Man, J. Mater. Chem., 20, 9322 (2010); https://doi.org/10.1039/c000334d.
O. De Los Cobos, B. Fousseret, M. Lejeune, F. Rossignol, M. Dutreilh- Colas, C. Carrion, C. Boissière, F. Ribot, C. Sanchez, X. Cattoën, M.W.C. Man and J.-O. Durand, Chem. Mater., 24, 4337 (2012); https://doi.org/10.1021/cm3022769.
N. Moitra, J.J.E. Moreau, X. Cattoën and M.W.C. Man, Chem. Commun., 46, 8416 (2010); https://doi.org/10.1039/c0cc03417g.
V.A. Kuksa, V.A. Pavlov and P.K. Lin, Bioorg. Med. Chem. Lett., 10, 1265 (2000); https://doi.org/10.1016/S0960-894X(00)00201-8.
N. Singh, R.C. Mulrooney, N. Kaur and J.F. Callan, Chem. Commun., 40, 4900 (2008); https://doi.org/10.1039/b813423e.
H. Sharma, N. Kaur, T. Pandiyan and N. Singh, Sens. Actuators B Chem., 166-167, 467 (2012); https://doi.org/10.1016/j.snb.2012.01.076.
K. Kaur, N. Kaur and N. Singh, Mater. Lett., 80, 78 (2012); https://doi.org/10.1016/j.matlet.2012.04.043.
H. Sharma, K. Narang, N. Singh and N. Kaur, Mater. Lett., 84, 104 (2012); https://doi.org/10.1016/j.matlet.2012.06.066.
A. Chandrasekaran, R.O. Day and R.R. Holmes, J. Am. Chem. Soc., 122, 1066 (2000); https://doi.org/10.1021/ja9926360.
C. Lee, W. Yang and R.G. Parr, Phys. Rev. B, 37, 785 (1988); https://doi.org/10.1103/PhysRevB.37.785.
A. Hartwig, Mutat. Res., 475, 113 (2001); https://doi.org/10.1016/S0027-5107(01)00074-4.
M.L. Lima, T. Cruz, L.E. Rodrigues, O. Bomfim, J. Melo, R. Correia, M. Porto, A. Cedro and E. Vicente, Diabetes Res. Clin. Pract., 83, 257 (2009); https://doi.org/10.1016/j.diabres.2008.11.019.
P. Bühlmann, E. Pretsch and E. Bakker, Chem. Rev., 98, 1593 (1998); https://doi.org/10.1021/cr970113+.
G. Farruggia, S. Iotti, L. Prodi, M. Montalti, N. Zaccheroni, P.B. Savage, V. Trapani, P. Sale and F.I. Wolf, J. Am. Chem. Soc., 128, 344 (2006); https://doi.org/10.1021/ja056523u.
Y. Liu, Z.-Y. Duan, H.-Y. Zhang, X.-L. Jiang and J.-R. Han, J. Org. Chem., 70, 1450 (2005); https://doi.org/10.1021/jo047968o.
H. Hama, T. Morozumi and H. Nakamura, Tetrahedron Lett., 48, 1859 (2007); https://doi.org/10.1016/j.tetlet.2006.12.147.
J.S. Yang, C.Y. Hwang and M.Y. Chen, Tetrahedron Lett., 48, 3097 (2007); https://doi.org/10.1016/j.tetlet.2007.02.120.
E. Tomat and S. Lippard, J. Inorg. Chem., 49, 9113 (2010); https://doi.org/10.1021/ic101513a.