Novel lipophilic lanthanide bis-phthalocyanines functionalized by pentadecylphenoxy groups: synthesis, characterization and UV-photostability

Molecules. 2012 Sep 7;17(9):10738-53. doi: 10.3390/molecules170910738.

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.

MeSH terms

  • Indoles / chemistry*
  • Isoindoles
  • Lanthanoid Series Elements / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Photolysis*
  • Ultraviolet Rays

Substances

  • Indoles
  • Isoindoles
  • Lanthanoid Series Elements
  • phthalocyanine