Abstract
The effect of peripheral alkyl, aryl, and meso-aza substitution on the thermal stability of BODIPYs in an argon or oxygen atmosphere has been analyzed using thermogravimetric study results. It has been shown that an increase in the length of 2,6-alkyl substituents to seven carbon atoms is accompanied by the growth of BODIPY thermal stability by 80°C. The greatest increase in the destruction temperature of BODIPY (by 100°C) is attained via the introduction of phenyl groups in the 1,3,5,7-positions of its dipyrromethenmethene framework. meso-Aza substitution does not almost produce any effect on the thermal stability of BODIPY dyes. The BODIPY destruction beginning temperature decreases by 60–90°C in the presence of air oxygen. The thermal stability of BODIPY tends to decrease with reducing degree and symmetry of alkyl substitution in the dipyrromethene framework. A lower thermal stability of BODIPY in comparison with zinc(II) dipyrromethenates is due to the participation of fluorine atoms in intramolecular redox processes.
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References
E. V. Antina, E. V. Rumyantsev, G. B. Guseva, et al., in Advances of Porphyrin Chemistry (Izd-vo NII Khimii, St. Petersburg, 2007), vol. 5 [in Russian].
E. V. Rumyantsev, G. B. Guseva, and E. V. Anitna, Zh. Fiz. Khim. 79, 219 (2005).
G. B. Guseva, E. V. Antina, A. S. Semeikin, et al., Russ. J. Phys. Chem. 80, 98 (2006).
G. B. Guseva, E. V. Antina, and A. I. Vyugin, J. Therm. Anal. Calorim. 92, 735 (2008).
G. B. Guseva, E. V. Antina, A. C. Semeikin, et al., Zh. Obshch. Khim. 72, 1391 (2002).
N. Sh. Lebedeva, E. V. Antina, M. B. Berezin, et al., Zh. Fiz. Khim. 74, 1165 (2000).
A. S. Semeikin, M. B. Berezin, O. M. Chernova, et al., Izv. Akad. Nauk, Ser. Khim., No. 8, 1712 (2003).
E. V. Rumyantsev, G. B. Guseva, E. V. Antina, et al., Zh. Obshch. Khim. 76, 143 (2006).
O. M. Chernova, M. B. Berezin, and E. V. Antina, Zh. Fiz. Khim. 77, 1002 (2003).
E. V. Rumyantsev, E. V. Antina, and M. B. Berezin, Zh. Fiz. Khim. 80, 1244 (2006).
E. V. Rumyantsev and E. V. Antina, Zh. Obshch. Khim. 77, 1363 (2007).
A. Loudet and K. Burgess, Chem. Rev. 107, 4891 (2007).
N. Boens, V. Leen, and W. Dehaen, Chem. Soc. Rev. 41, 1130 (2012).
M. Benstead, G. H. Mehl, and R. W. Boyle, Tetrahedron 67, 3573 (2011).
A. Kamkaew, S. H. Lim, H. B. Lee, et al., Chem. Soc. Rev. 42, 77 (2013).
R. Ziessel, G. Ulrich, and A. Harriman, New J. Chem. 31, 496 (2007).
E. V. Antina, G. B. Guseva, E. V. Rumyantsev, and N. A. Dudina, Zh. Obshch. Khim. 79, 1900 (2009).
S. L. Yutanova, M. B. Berezin, A. S. Semeikin, et al., Zh. Obshch. Khim. 83, 492 (2013).
E. V. Antina, M. B. Berezin, N. A. Dudina, et al., Zh. Neorg. Khim. 59, 1427 (2014).
G. B. Guseva, L. A. Antina, E. V. Antina, and A. I. Vyugin, Thermochim. Acta 544, 54 (2012).
E. V. Antina, N. A. Dudina, M. B. Berezin, et al., Zh. Neorg. Khim. 61, 836 (2016).
R. Gresser, A. Hoyer, M. Hummert, et al., Dalton Trans. 40, 3476 (2011).
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Original Russian Text © N.A. Bumagina, A.Yu. Kritskaya, E.V. Antina, M.B. Berezin, A.I. V’yugin, 2018, published in Zhurnal Neorganicheskoi Khimii, 2018, Vol. 63, No. 10, pp. 1310–1316.
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Bumagina, N.A., Kritskaya, A.Y., Antina, E.V. et al. Effect of Alkyl, Aryl, and meso-Aza Substitution on the Thermal Stability of BODIPY. Russ. J. Inorg. Chem. 63, 1326–1332 (2018). https://doi.org/10.1134/S0036023618100030
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DOI: https://doi.org/10.1134/S0036023618100030