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Molecules 2012, 17(9), 10738-10753;

Novel Lipophilic Lanthanide Bis-Phthalocyanines Functionalized by Pentadecylphenoxy Groups: Synthesis, Characterization and UV-Photostability

Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland
Department of Engineering for Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy
Author to whom correspondence should be addressed.
Received: 3 August 2012 / Revised: 10 August 2012 / Accepted: 3 September 2012 / Published: 7 September 2012
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanines)
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Novel sandwich-type phthalocyanines containing a rare earth metal core (Pr, Nd, Eu–Lu) and macrocycles peripherally substituted by pentadecylphenoxy groups were synthesized using a cardanol-based phthalonitrile precursor and the respective lanthanide acetate. Additionally, the metal free-base analog compound was studied for comparison. The purified reaction products were all found to be thick and viscous substances at room temperature, showing liquid crystalline behavior with a distinct increase in fluidity at ca. 40 °C. The complexes are readily soluble in chloroalkyl solvents and dissolve fairly well in DMF with some tendency to form aggregates. Besides they are strongly hydrophobic and reveal a peculiar affinity for lipophilic media. The compounds have been characterized by UV-Vis (absorption and emission), FTIR, MS and DSC methods. Photochemical activity in the liquid phase (dimethylformamide, dichloromethane, mineral oil) and the degree of photodegradation demonstrated under constant UV-irradiation (λ = 352 nm) have been analyzed and discussed in terms of photostability. View Full-Text
Keywords: lanthanide bis-phthalocyanines; cardanol; UV-Vis spectroscopy; photostability lanthanide bis-phthalocyanines; cardanol; UV-Vis spectroscopy; photostability

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Słota, R.; Dyrda, G.; Hofer, M.; Mele, G.; Bloise, E.; Sole, R. Novel Lipophilic Lanthanide Bis-Phthalocyanines Functionalized by Pentadecylphenoxy Groups: Synthesis, Characterization and UV-Photostability. Molecules 2012, 17, 10738-10753.

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