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

作者：Slota Rudolf^*; Dyrda Gabriela; Hofer Maria; Mele Giuseppe; Bloise Ermelinda; del Sole Roberta

来源：Molecules, 2012, 17(9): 10738-10753.

DOI：10.3390/molecules170910738

• lanthanide bis-phthalocyanines
• cardanol
• UV-Vis spectroscopy
• photostability

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 degrees 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 (lambda = 352 nm) have been analyzed and discussed in terms of photostability.

• 出版日期2012-9