Molecules 2012, 17(9), 10738-10753; doi:10.3390/molecules170910738
Article

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

1 Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland 2 Department of Engineering for Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy
* Author to whom correspondence should be addressed.
Received: 3 August 2012; in revised form: 10 August 2012 / Accepted: 3 September 2012 / Published: 7 September 2012
(This article belongs to the Special Issue Tetrapyrroles, Porphyrins and Phthalocyanine)
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Abstract: 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.
Keywords: lanthanide bis-phthalocyanines; cardanol; UV-Vis spectroscopy; photostability

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MDPI and ACS Style

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.

AMA Style

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(9):10738-10753.

Chicago/Turabian Style

Słota, Rudolf; Dyrda, Gabriela; Hofer, Maria; Mele, Giuseppe; Bloise, Ermelinda; Sole, Roberta del. 2012. "Novel Lipophilic Lanthanide Bis-Phthalocyanines Functionalized by Pentadecylphenoxy Groups: Synthesis, Characterization and UV-Photostability." Molecules 17, no. 9: 10738-10753.

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