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Synthesis and Antimicrobicidal Activity of Phenothiazinophanes: A New Class of Permanent Fluorescence Sensing Stilbenophanes
Corresponding Author(s) : Perumal Rajakumar
Asian Journal of Chemistry,
Vol. 27 No. 12 (2015): Vol 27 Issue 12
Abstract
The synthesis, characterization and antimicrobicidal activity of phenophiazinophane and chiral phenothiazinophanes are described. The synthesized compounds also exhibits excellent fluorescent sensing properties.
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- M. Sakamoto, A. Ueno and H. Mihara, Chem. Commun., 1741 (2000); doi:10.1039/b003786i.
- (a) A.J. Heeger, Angew. Chem. Int. Ed., 40, 2591 (2001); doi:10.1002/1521-3773(20010716)40:14<2591::AID-ANIE2591>3.0.CO;2-0; (b) A.G. Mac Diarmid, Angew. Chem. Int. Ed., 40, 2581 (2001); doi:10.1002/1521-3773(20010716)40:14<2581::AID-ANIE2581>3.0.CO;2-2.
- (a) M.T. Bernius, M. Inbasekaran, J. O’Brien and W. Wu, Adv. Mater., 12, 1737 (2000); doi:10.1002/1521-4095(200012)12:23<1737::AID-ADMA1737>3.0.CO;2-N; (b) A. Kraft, A.C. Grimsdale and A.B. Holmes, Angew. Chem. Int. Ed., 37, 402 (1998); doi:10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9.
- (a) X. Zhang, A.S. Shetty and S.A. Jenekhe, Macromolecules, 32, 7422 (1999); doi:10.1021/ma990960+; (b) M.M. Alam and S.A. Jenekhe, Chem. Mater., 14, 4775 (2002); doi:10.1021/cm020600s.
- (a) J.J.M. Halls, C.A. Walsh, N.C. Greenham, E.A. Marseglia, R.H. Friend, S.C. Moratti and A.B. Holmes, Nature, 376, 498 (1995); doi:10.1038/376498a0; (b) A.C. Arias, J.D. MacKenzie, R. Stevenson, J.J.M. Halls, M. Inbasekaran, E.P. Woo, D. Richards and R.H. Friend, Macromolecules, 34, 6005 (2001); doi:10.1021/ma010240e.
- H. Antoniadis, B.R. Hsieh, M.A. Abkowitz, S.A. Jenekhe and M. Stolka, Synth. Met., 62, 265 (1994); doi:10.1016/0379-6779(94)90215-1.
- (a) A. Babel and S.A. Jenekhe, J. Phys. Chem. B, 107, 1749 (2003); doi:10.1021/jp0215062; (b) A. Babel and S.A. Jenekhe, Macromolecules, 36, 7759 (2003); doi:10.1021/ma034717t.
- (a) S.A. Sapp, G.A. Sotzing and J.R. Reynolds, Chem. Mater., 10, 2101 (1998); doi:10.1021/cm9801237; (b) F. Fungo, S.A. Jenekhe and A.J. Bard, Chem. Mater., 15, 1264 (2003); doi:10.1021/cm0210445.
- N.S. Cho, J.-H. Park, S.-K. Lee, J. Lee, H.-K. Shim, M.-J. Park, D.-H. Hwang and B.-J. Jung, Macromolecules, 39, 177 (2006); doi:10.1021/ma051784+.
- H. Bauer, F. Stier, C. Petry, A. Knorr, C. Stadler and H.A. Staab, Eur. J. Org. Chem., 2001, 3255 (2001); doi:10.1002/1099-0690(200109)2001:17<3255::AID-EJOC3255>3.0.CO;2-0.
- P.J. Raval and R.K. Desai, ARKIVOV, 21 (2005); doi:10.3998/ark.5550190.0006.d03.
- R. Ddhibom and T. Fkstramd, Arch. Int. Pharmacodyn., 159, 70 (1996).
- C.S. Weil, Biomertics, 8, 249 (1952); doi:10.2307/3001557.
- B.N. Harpen, J. Am. Med. Assoc., 129, 1419 (1945).
- J.D. Genzer, M.N. Lewis, F.H. McMillan and J.A. King, J. Am. Chem. Soc., 75, 2506 (1953); doi:10.1021/ja01106a510.
- L.J. Dushay, Rev. Can. Biol., 20, 321 (1961).
- J.R. Douglass, N.F. Baker and M.W. Longwest, Am. J. Vet. Res., 17, 318 (1956).
- (a) R.T. Lai, E.F. Fabrizio, L. Lu, S.A. Jenekhe and A. Bard, J. Am. Chem. Soc., 123, 9112 (2001); doi:10.1021/ja0102235; (b) D. Sun, S.V. Rosokha and J.K. Kochi, J. Am. Chem. Soc., 126, 1388 (2004); doi:10.1021/ja038746v.
- P. Rajakumar and R. Kanagalatha, Tetrahedron Lett., 48, 8496 (2007); doi:10.1016/j.tetlet.2007.09.161.
- P. Rajakumar and R. Kanagalatha, Tetrahedron, 62, 9735 (2006); doi:10.1016/j.tet.2006.07.064.
- M.S. Nair, U. Sudhir, S. Joly and N.P. Rath, Tetrahedron, 55, 7653 (1999); doi:10.1016/S0040-4020(99)00381-6.
References
M. Sakamoto, A. Ueno and H. Mihara, Chem. Commun., 1741 (2000); doi:10.1039/b003786i.
(a) A.J. Heeger, Angew. Chem. Int. Ed., 40, 2591 (2001); doi:10.1002/1521-3773(20010716)40:14<2591::AID-ANIE2591>3.0.CO;2-0; (b) A.G. Mac Diarmid, Angew. Chem. Int. Ed., 40, 2581 (2001); doi:10.1002/1521-3773(20010716)40:14<2581::AID-ANIE2581>3.0.CO;2-2.
(a) M.T. Bernius, M. Inbasekaran, J. O’Brien and W. Wu, Adv. Mater., 12, 1737 (2000); doi:10.1002/1521-4095(200012)12:23<1737::AID-ADMA1737>3.0.CO;2-N; (b) A. Kraft, A.C. Grimsdale and A.B. Holmes, Angew. Chem. Int. Ed., 37, 402 (1998); doi:10.1002/(SICI)1521-3773(19980302)37:4<402::AID-ANIE402>3.0.CO;2-9.
(a) X. Zhang, A.S. Shetty and S.A. Jenekhe, Macromolecules, 32, 7422 (1999); doi:10.1021/ma990960+; (b) M.M. Alam and S.A. Jenekhe, Chem. Mater., 14, 4775 (2002); doi:10.1021/cm020600s.
(a) J.J.M. Halls, C.A. Walsh, N.C. Greenham, E.A. Marseglia, R.H. Friend, S.C. Moratti and A.B. Holmes, Nature, 376, 498 (1995); doi:10.1038/376498a0; (b) A.C. Arias, J.D. MacKenzie, R. Stevenson, J.J.M. Halls, M. Inbasekaran, E.P. Woo, D. Richards and R.H. Friend, Macromolecules, 34, 6005 (2001); doi:10.1021/ma010240e.
H. Antoniadis, B.R. Hsieh, M.A. Abkowitz, S.A. Jenekhe and M. Stolka, Synth. Met., 62, 265 (1994); doi:10.1016/0379-6779(94)90215-1.
(a) A. Babel and S.A. Jenekhe, J. Phys. Chem. B, 107, 1749 (2003); doi:10.1021/jp0215062; (b) A. Babel and S.A. Jenekhe, Macromolecules, 36, 7759 (2003); doi:10.1021/ma034717t.
(a) S.A. Sapp, G.A. Sotzing and J.R. Reynolds, Chem. Mater., 10, 2101 (1998); doi:10.1021/cm9801237; (b) F. Fungo, S.A. Jenekhe and A.J. Bard, Chem. Mater., 15, 1264 (2003); doi:10.1021/cm0210445.
N.S. Cho, J.-H. Park, S.-K. Lee, J. Lee, H.-K. Shim, M.-J. Park, D.-H. Hwang and B.-J. Jung, Macromolecules, 39, 177 (2006); doi:10.1021/ma051784+.
H. Bauer, F. Stier, C. Petry, A. Knorr, C. Stadler and H.A. Staab, Eur. J. Org. Chem., 2001, 3255 (2001); doi:10.1002/1099-0690(200109)2001:17<3255::AID-EJOC3255>3.0.CO;2-0.
P.J. Raval and R.K. Desai, ARKIVOV, 21 (2005); doi:10.3998/ark.5550190.0006.d03.
R. Ddhibom and T. Fkstramd, Arch. Int. Pharmacodyn., 159, 70 (1996).
C.S. Weil, Biomertics, 8, 249 (1952); doi:10.2307/3001557.
B.N. Harpen, J. Am. Med. Assoc., 129, 1419 (1945).
J.D. Genzer, M.N. Lewis, F.H. McMillan and J.A. King, J. Am. Chem. Soc., 75, 2506 (1953); doi:10.1021/ja01106a510.
L.J. Dushay, Rev. Can. Biol., 20, 321 (1961).
J.R. Douglass, N.F. Baker and M.W. Longwest, Am. J. Vet. Res., 17, 318 (1956).
(a) R.T. Lai, E.F. Fabrizio, L. Lu, S.A. Jenekhe and A. Bard, J. Am. Chem. Soc., 123, 9112 (2001); doi:10.1021/ja0102235; (b) D. Sun, S.V. Rosokha and J.K. Kochi, J. Am. Chem. Soc., 126, 1388 (2004); doi:10.1021/ja038746v.
P. Rajakumar and R. Kanagalatha, Tetrahedron Lett., 48, 8496 (2007); doi:10.1016/j.tetlet.2007.09.161.
P. Rajakumar and R. Kanagalatha, Tetrahedron, 62, 9735 (2006); doi:10.1016/j.tet.2006.07.064.
M.S. Nair, U. Sudhir, S. Joly and N.P. Rath, Tetrahedron, 55, 7653 (1999); doi:10.1016/S0040-4020(99)00381-6.