Synthesis, Spectral, Luminescence and Photochemical Properties of the Chlorin е6 Tricationic Derivative with Trimethylammonio Groups

Evgenii A. Venediktov,^a@ Elena Yu. Tulikova,^a Ekaterina P. Rozhkova,^a,b Irina S. Khudyaeva,^c Dmitry V. Belykh,^с and Dmitry B. Berezin^b

^aKrestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, Russian Federation

^bIvanovo State University of Chemistry and Technology, Research Institute of Macroheterocyclic Compounds, 153000 Ivanovo, Russian Federation

^cInstitute of Chemistry of Komi Republic Scientific Centre of Ural Branch of Russian Academy of Sciences, 167982 Syktyvkar, Russian Federation

^@Corresponding author E-mail: eav@isc-ras.ru

DOI: 10.6060/mhc170404v

Macroheterocycles 2017 10(3) 295-300

The synthesis, spectral and luminescence properties of 3(1),3(2)-bis(N’,N’’,N’’’-trimethylaminomethyl iodide)chlorin е₆ 13(1)-(N’,N’,N’’’-trimethylammonioethyl iodide)amide-15(2),17(3)-dimethyl ester (1), and its photochemical reactions with molecular oxygen in pyridine are described. The absorbance of comp. 1 with molar absorption coefficient equal to 5.8∙10⁴ M^-1·cm^-1 at 661 nm first band maximum is typical for chlorin e₆ compounds family. In the light in pyridine solutions saturated with air oxygen, comp. 1 showed the fluorescence with maximum at 667 nm and quantum yield of 0.13 as well as the ¹O₂ luminescence with quantum yield of 0.59. The inhibition method by hydroquinone of 1 photooxidation the role of the reaction with ¹O₂ was confirmed and its contribution of 30 % in this process was detected. The last result is explained by the competitive chemical interaction between 1 excited triplet molecules and O₂. The rate constant of the second order reaction between 1 and ¹O₂was determined to be 2.0∙10⁴ M^-1∙s^-1.

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Synthesis, Spectral, Luminescence and Photochemical Properties of the Chlorin е6 Tricationic Derivative with Trimethylammonio Groups

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