Abstract
A series of N,N′,N″-tris[aryl(hetaryl)methylideneamino]guanidines have been synthesized in good yields by condensation of N,N′,N″-triaminoguanidine hydrochloride with aromatic and heteroaromatic aldehydes. All compounds have been characterized by 1H and 13C NMR and FT-IR spectra, and the molecular structure of one compound has been determined by single crystal X-ray diffraction. Study of the optical properties of the title compounds in the presence of fluoride ions has shown selective color change from colorless to yellow and purple due to red shift in their UV-Vis absorption spectra.
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Magnum, M.G. and Ouart, D.C., US Patent Appl. Pub. no. 2001/0017175 A1, 2001.
Larsen, S.D., Vaillancourt, V.A., May, P.D., Tanis, S.P., Meglasson, M.D., and Schostarez, H.J., US Patent no. 5994577, 1999.
Ishikawa, T. and Isobe, T., Chem. Eur. J., 2002, vol. 8, p. 257. doi 10.1002/1521-3765(20020201) 8:3552::AID-CHEM5523.0.CO;2-T
Müller, I.M., Möller, D., and Föcker, K., Chem. Eur. J., 2005, vol. 11, p. 257. doi 10.1002/chem.200401260
Müller, I.M. and Robson, R., Angew. Chem., Int. Ed., 2000, vol. 39, p. 257. doi 10.1002/1521-3773 (20001201)39:234357::AID-ANIE43573.0.CO;2-0
Müller, I.M., Möller, D., and Schalley, C.A., Angew. Chem., Int. Ed., 2005, vol. 44, p. 257. doi 10.1002/anie.200461800
Müller, I.M. and Möller, D., Eur. J. Inorg. Chem., 2005, vol. 2, p. 257. doi 10.1002/ejic.200400526
Müller, I.M. and Möller, D., Angew. Chem., Int. Ed., 2005, vol. 44, p. 257. doi 10.1002/anie.200463034
Föcker, K., Angew. Chem., Int. Ed., 2008, vol. 47, p. 257. doi 10.1002/anie.200703789
Szabo, J., Karger, K., Bucher, N., and Maas, G., Beilstein J. Org. Chem., 2014, vol. 10, p. 257. doi 10.3762/bjoc.10.234
Scott, F.L., Cashman, M., and Reilly, J., J. Am. Chem. Soc., 1952, vol. 74, p. 257. doi 10.1021/ja01142a603
Szabo, J. and Maas, G., Z. Naturforsch., Teil B, 2013, vol. 68, p. 207. doi 10.5560/znb.2013-3023
Coburn, M.D., Buntain, G.A., Harris, B.W., Hiskey, M.A., Lee, K.Y., and Ott, D.G., J. Heterocycl. Chem., 1991, vol. 28, p. 257. doi 10.1002/ jhet.5570280844
Szabo, J., Greiner, J., and Maas, G., Beilstein J. Org. Chem., 2017, vol. 13, p. 257. doi 10.3762/bjoc.13.57
Potts, K.T. and Hirsch, C.A., J. Org. Chem., 1968, vol. 33, p. 257. doi 10.1021/jo01265a027
Cardillo, P., Dellavedova, M., Gigante, L., Lunghi, A., Pasturenzi, C., Salatelli, E., and Zanirato, P., Eur. J. Org. Chem., 2012, vol. 6, p. 257. doi 10.1002/ ejoc.201101450
Klapötke, T.M., Martin, F.A., and Stierstorfer, J., Angew. Chem., Int. Ed., 2011, vol. 50, p. 257. doi 10.1002/ anie.201100300
Wingborg, N. and Latypov, N.V., Propellants, Explos., Pyrotech., 2003, vol. 28, p. 257. doi 10.1002/ prep.200300022
Tobey, S.L. and Anslyn, E.V., J. Am. Chem. Soc., 2003, vol. 125, p. 257. doi 10.1021/ja030507k
Schmuck, C. and Geiger, L., J. Am. Chem. Soc., 2004, vol. 126, p. 257. doi 10.1021/ja048587v
Schmuck, C. and Schwegmann, M., Org. Biomol. Chem., 2006, vol. 4, p. 257. doi 10.1039/b516019g
McCleskey, S.C., Metzger, A., Simmons, C.S., and Anslyn, E.V., Tetrahedron, 2002, vol. 58, p. 621. doi 10.1016/S0040-4020(01)01093-6
Wang, B., Zhang, P.Z., Chen, X., Jia, A.Q., and Zhang, Q.F., Z. Naturforsch., Teil b, 2018, vol. 73, p. 601. doi 10.1515/znb-2018-0102
Müller, I.M., Spillmann, S., Franck, H., and Pietschnig, R., Chem. Eur. J., 2004, vol. 10, p. 257. doi 10.1002/chem.200305564
Bose, P., Ahamed, B.N., and Ghosh, P., Org. Biomol. Chem., 2011, vol. 9, p. 257. doi 10.1039/c0ob00947d
Smart and Saint+ for Windows NT (version 6.02a), Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
Sheldrick, G.M., SADABS, Göttingen, Germany: Univ. of Göttingen, 1996.
Sheldrick, G.M., SHELXTL (version 5.1), Software Reference Manual, Madison, Wisconsin, USA: Bruker AXS, 1997.
Sheldrick, G.M., Acta Crystallogr., Sect. C., 2015, vol. 71, p. 257. doi 10.1107/S2053229614024218
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This project was financially supported by the National Natural Science Foundation of China (project no. 21372007).
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Ji, J., Chen, X., Zhang, PZ. et al. Synthesis of Novel N,N′,N″-Tris[aryl(hetaryl)-methylideneamino]guanidine Derivatives as Efficient and Selective Colorimetric Sensors for Fluoride Ion. Russ J Org Chem 55, 1399–1406 (2019). https://doi.org/10.1134/S1070428019090215
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DOI: https://doi.org/10.1134/S1070428019090215