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

Molecules

Rudolf Słota¹  Gabriela Dyrda¹  Maria Hofer¹  Giuseppe Mele¹  Ermelinda Bloise¹ 

[1] ¹Faculty of Chemistry, Opole University, ul. Oleska 48, 45-052 Opole, Poland ²Department of Engineering for Innovation, University of Salento, Via Arnesano, 73100 Lecce, Italy

关键词: lanthanide bis-phthalocyanines;    cardanol;    UV-Vis spectroscopy;    photostability;   

DOI  :  10.3390/molecules170910738

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.