Abstract
(1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)(1,2,3,7,8-pentamethyldipyrrolylmethen-9-yl)-methane and bis(1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)trifluoromethylmethane hydrobromides were synthesized and characterized spectrally (1H NMR, IR, electron absorption spectra). A comparative study was performed of the effect of the bonding site (α- or β-position of the dipyrrolylmethene) with the methane structural fragment connecting two dipyrrolylmethene chromophores, and trifluoromethyl group on the spectral properties of the molecules of compounds dissolved in organic solvents of different nature and their resistance to thermal oxidative degradation.
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References
Falk, N., The Chemistry of Linear Oligopyrroles and Bile Pigments, New York: Wien, 1989.
Zang, Y., Thompson, A., Retting, S.J., and Dolphin, D., J. Am. Chem. Soc., 1998, vol. 120, no. 7, p. 13537.
Thompson, A. and Dolphin, D., J. Org. Chem., 2000, vol. 65, no. 10, p. 7870.
Garcia-Moreno, I., Costela, A., and Campo, L., J. Phys. Chem. (A), 2004, vol. 108, no. 17, p. 3315.
Wood, T.E., Ross, A.C., Dalgleish, N.D., Power, E.D., Thompson, A., Chen, X., and Okamoto, Y., J. Org. Chem., 2005, vol. 70, no. 2, p. 9967.
Berezin, M.B., Chernova, O.M., Semeikin, A.S., Shatunov, P.A., Pashanova, N.A., and Berezin, D.B., Molecules, 2000, no. 5, p.809; http://www.mdpi.org.
Berezin, M.B., Termokhimiya sol’vatatsii khlorofilla i rodstvennykh soedinenii (Thermochemistry of Solvation of Chlorophyll and Related Compounds), Moscow: Krasand, 2008.
Antina, E.V. and Rumyantsev, E.V., Khimiya bilirubina i ego analogov (Chemistry of Bilirubin and Analogues), Moscow: Krasand, 2009.
Guseva, G.B., Dudina, N.A., Antina, E.V., V’yugin, A.I., and Semeikin, A.S., Zh. Obshch. Khim., 2008, vol. 78, no. 6, p. 987.
Berezin, M.B., Semeikin, A.S., Antina, E.V., Pashanova, N.A., Lebedeva, N.Sh., and Bukushina, G.B., Zh. Obshch. Khim., 1999, vol.69, no. 12, p. 2040.
Zakharova, S.P., Rumyantsev, E.V., Antina, E.V., and Semeikin, A.S., Koord. Khim., 2005, vol. 31, no. 5, p. 353.
Terenin, A.N., Fotonika molekul krasitelei i rodstvennykh soedinenii (Photonics of the Molecules of Dyes and Related Compounds), Leningrad: Nauka, 1967.
Mroginski, M.A., Nemeth, K., and Bauschlicher, T., J. Phis. Chem. (A), 2005, vol. 109, no. 10, p. 2139.
Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.
Berezin, M.B., Semeikin, A.S., V’yugin, A.I., and Krestov, G.A., Izv. Rus. Akad. Nauk, Ser. Khim., 1993, no. 3, p.495.
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Original Russian Text © M.B. Berezin, A.S. Semeikin, S.L. Yutanova, E.V. Antina, G.B. Guseva, A.I. V’yugin, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 7, pp. 1189–1194.
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Berezin, M.B., Semeikin, A.S., Yutanova, S.L. et al. Synthesis and properties of (1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)-(1,2,3,7,8-pentamethyldipyrrolylmethen-9-yl)methane and bis(1,2,3,7,9-pentamethyldipyrrolylmethen-8-yl)trifluoromethylmethane dihydrobromides. Russ J Gen Chem 82, 1287–1292 (2012). https://doi.org/10.1134/S1070363212070183
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DOI: https://doi.org/10.1134/S1070363212070183