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ISSN 1998-9539

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. Berezinb
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:
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 1O2 was determined to be 2.0∙104 M-1∙s-1.


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