Abstract
Novel photochromic spirobipyrans containing benzothiazole group in the 2H-chromene moiety have been synthesized. The spirobipyrans combine with Co2+, Ni2+, Zn2+, and Cu2+ ions to give intensely colored complexes of merocyanine form with long-wavelength absorption bands at λ > 600 nm.
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REFERENCES
Klajn, R., Chem. Soc. Rev., 2014, vol. 43, pp. 148–184. https://doi.org/10.1039/C3CS60181A
Molecular Switches, Feringa, B.L. and Browne, W.R., Eds., Weinheim: Wiley, 2011.
Paramonov, S.V., Lokshin, V., and Fedorova, O.A., J. Photochem. Photobiol. C: Photochem. Rev., 2011, vol. 12, pp. 209–236. https://doi.org/10.1016/j.jphotochemrev.2011.09.001
Atabekyan, L.S. and Chibisov, A.K., High Energy Chem., 2018, vol. 52, pp. 230–235. https://doi.org/10.1134/S0018143918030025
Gao, M., Shen, B., Zhou, J., Kapre, R., Louie, A.Y., and Shaw, J.T., ACS Omega, 2020, vol. 5, рр. 14759−14766.https://doi.org/10.1021/acsomega.0c01534
Ausaf, AliA., Kharbash, R., and Kim, Y., Anal. Chim. Acta, 2020, vol. 1110, pp. 199–223. https://doi.org/10.1016/j.aca.2020.01.057
Heng, S., Reineck, P., Vidanapathirana, A.K., Pullen, B.J., Drumm, D.W., Ritter, L.J., Schwarz, N., Bonder, C.S., Psaltis, P.J., Thompson, J.G., Gibson, B.C., Nicholls, S.J., and Abell, A.D., ACS Omega, 2017, vol. 2, рр. 6201−6210.https://doi.org/10.1021/acsomega.7b00923
Feuerstein, T.J., Müller, R., Barner-Kowollik, C., and Roesky, P.W., Inorg. Chem., 2019, vol. 58, pp. 15479− 15486.https://doi.org/10.1021/acs.inorgchem.9b02547
Zhang, Y., Zhou, Q., Tian, Na., Li, C., and Wang, X., Inorg. Chem., 2017, vol. 56, p. 1865. https://doi.org/10.1021/acs.inorgchem.6b02459
Bertelson, R.C., in Photochromism,Techniques in Chemistry, Brown, G.H., Ed., New York: Wiley, 1971, vol. III.
Lu, N.T., Nguyen, V.N., Kumar, S., and McCurdy, A., Org. Chem., 2005, vol. 70, pp. 9067–9070. https://doi.org/10.1021/jo051449j
McCurdy, A., Kawaoka, A.M., Thai, H., and Yoon, S.C., Tetrahedron Lett., 2001, vol. 142, pp. 7763–7766. https://doi.org/10.1016/S0040-4039(01)01677-X
Kumar, S., Chau, C., Chau, G., and McCurdy, A., Tetrahedron, 2008, vol. 64, pp. 7097–7105. https://doi.org/10.1016/j.tet.2008.05.083
Gabbut, C.D., Hepworth, J.D., and Heron, B.M., Dyes Pigm., 1999, vol. 42, pp. 35–43. https://doi.org/10.1016/S0143-7208(99)00007-8
Voloshin, N.A., Chernyshev, A.V., Metelitsa, A.V., Gaeva, E.B., and Minkin, V.I., Russ. Chem. Bull., 2011, no. 9, pp. 1888–1893. https://doi.org/10.1007/s11172-011-0289-2
Rostovtseva, I.A., Chernyshev, A.V., Tkachev, V. V., Aldoshin, S.M., Voloshin, N.A., Metelitsa, A.V., Makarova, N.I., and Minkin, V.I., Russ. Chem. Bull., 2015, no. 3, pp. 677–682. https://doi.org/10.1007/s11172-015-0918-2
Schiele, C., Wilhelm, A., Hendriks, D., Stepec, M., and Paal, G., Tetrahedron, 1968, vol. 24, pp. 5029–5036. https://doi.org/10.1016/S0040-4020(01)88412-X
Löwenbein, A. and Katz, W., Chem. Ber., 1926, vol. 59, pp. 1377–1383. https://doi.org/10.1002/cber.19260590704
ACKNOWLEDGMENTS
Spectral studies were performed using the equipment of the Molecular Spectroscopy Shared Facility Center, Southern Federal University.
Funding
This work was supported by the Ministry of Science and Higher Education of the Russian Federation, project no. 0852–2020–00–19.
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Translated by I. Kudryavtsev
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Solov’eva, E.V., Voloshin, N.A., Chernyshev, A.V. et al. Novel Photo- and Ionochromic Benzothiazole-Substituted Spirobipyrans. Dokl Chem 494, 141–144 (2020). https://doi.org/10.1134/S0012500820090050
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DOI: https://doi.org/10.1134/S0012500820090050