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Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion
Authors: Lijewski Sebastian | Tydlitát Jiří | Czarczynska-Goslinska Beata | Klikar Milan | Mielcarek Jadwiga | Goslinski Tomasz | Sobotta Lukasz
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: APPLIED SCIENCES-BASEL
Publisher name: MDPI
Place: BASEL
Page from-to: 2576
Titles:
Language Name Abstract Keywords
cze Syntéza a fyzikálně-chemické vlastnosti [(1R,2S,5R)-2-isopropyl-5-methylcyklohexyloxy]-thiofen-5-yl-substituovaných tetrapyrazinoporfyrazinů s manganatými ionty Byly syntetizovány tetrapyrazinoporfyraziny s postranními menthol-thiofenovými substituenty, produkty byly čištěny sloupcovou chromatografií. Deriváty byly charakterizovány UV-Vis a NMR spektroskopií. Byly stanoveny fotochemická stabilita a kvantový výtěžek singletového kyslíku. Menthol; fotostabilita; ftalocyaniny; sigletový kyslík; terpeny
eng Synthesis and Physicochemical Properties of [(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]-thiophen-5-yl-substituted Tetrapyrazinoporphyrazine with Magnesium(II) Ion Tetrapyrazinoporphyrazine with peripheral menthol-thiophenyl substituents was synthesized using Linstead conditions and purified by flash column chromatography. The optimized synthetic and purification procedures allowed us to obtain a new macrocycle with 36% yield. Tetrapyrazinoporphyrazine derivative was characterized by UV-Vis and NMR spectroscopy, as well as MS spectrometry. Complex NMR studies using 1D and 2D NMR techniques allowed the analysis of the bulky menthol-thiophenyl substituted periphery of the new macrocycle. Further, photochemical stability and singlet oxygen quantum yield were determined by indirect method with diphenylisobenzofuran. The new tetrapyrazinoporphyrazine revealed low generation of singlet oxygen with a quantum yield of singlet oxygen formation at 2.3% in dimethylformamide. In turn, the macrocycle under irradiation with visible light presented very high stability with quantum yield for photostability of 9.59 x 10(-6) in dimethylformamide, which figures significantly exceed the border for its classification as a stable porphyrinoid (10(-4)-10(-5)). menthol; photostability; phthalocyanines; singlet oxygen; terpenes

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