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Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups
Authors: Černý Jiří | Dokladalová Lenka | Horaková Petra | Lyčka Antonín | Mikysek Tomáš | Bureš Filip
Year: 2017
Type of publication: článek v odborném periodiku
Name of source: Chemistry Central Journal
Publisher name: Biomed Central, Ltd.
Place: London
Page from-to: "31-1"-"31-9"
Titles:
Language Name Abstract Keywords
cze Příprava a charakterizace nových dvouvrstevných ftalocyaninů obsahujících vzácný kov substituovaných 5-brom-2-thienylskupinou Byla připravena série bisftalocyaninů obsahujících vzácný kov (praseodym, samarium a gadolinium) a nesoucích 5-brom-2-thienyl skupinu. Sloučeniny byly charakterizovány UV-vis, NIR, FT-IR, MS, termorgavimetrií, elementární analýzou a elektrochemicky. Atom bromu způsobuje významnou změnu paramagnetismu molekul, produkci singletového kyslíku, pozici HOMO orbitalu a spektrální charakteristiky. V roztoku existují sloučeniny ve dvou formách (neutrální a/nebo redukované) a to v závislosti na typu rozpouštědla a vzácného kovu. bisftalocyaniny; vzácné kovy; UV-Vis spektroskopie; NIR spektroskopie; redukce; cyklická voltametrie; termogravimetrie
eng Preparation and characterization of novel double-decker rare-earth phthalocyanines substituted with 5-bromo-2-thienyl groups Background: A series of rare-earth bisphthalocyanines of praseodymium, samarium and gadolinium bearing 5-bromo-2-thienyl substituents were prepared for the first time. Results: Three bis[octakis(5-bromo-2-thienyl)] rare-earth metal(III) bisphthalocyanine complexes (Pr, Sm, Gd) were synthesized for the first time. The new compounds were characterized by UV-vis, NIR, FT-IR, mass spectroscopy and thermogravimetry as well as elementary analysis and electrochemistry. Production of singlet oxygen was also estimated using 9,10-dimethylanthracene method. Conclusions: The bromine substituent causes significant changes in molecule paramagnetism, singlet oxygen production, HOMO position and spectral characteristics. The compounds in solutions exist in two forms (neutral and/or reduced) depending on the solvent and rare-earth metal. Moreover, the compounds exhibit much increased stability under acid conditions compared with non-brominated derivatives. Rare-earth bisphthalocyanines; UV-vis spectroscopy; NIR spectroscopy; Singlet oxygen production; Reduction; Cyclic voltammetry; Acid stability; Thermogravimetry

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