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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,* , 1, 1, 2, 2 and 2
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 lanthanide bis-phthalocyanines; cardanol; UV-Vis spectroscopy; photostability
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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