Fluorinated Phthalocyanine/Silver Nanoconjugates for Multifunctional Biological Applications.

In this study, a new phthalonitrile derivative namely 4-[(2,4-difluorophenyl)ethynyl]phthalonitrile (1) and its metal phthalocyanines (2 and 3) were synthesized. The resultant compounds were conjugated to silver nanoparticles and characterized using transmission electron microscopy (TEM) images. The biological properties of compounds (1-3), their nanoconjugates (4-6), and silver nanoparticles (7) were examined for the first time in this study. The antioxidant activities of biological candidates (1-7) were studied by applying the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay. The highest antioxidant activity was obtained 97.47 % for 200 mg/L manganese phthalocyanine-silver nanoconjugates (6). The antimicrobial and antimicrobial photodynamic therapy (APDT) activities of biological candidates (1-7) were examined using a micro-dilution assay. The highest MIC value was obtained 8 mg/L for nanoconjugate 6 against E. hirae. The studied compounds and their silver nanoconjugates exhibited high APDT activities against all the studied microorganisms. The most effective APDT activities were obtained 4 mg/L for nanoconjugates (5 and 6) against L. pneumophila and E. hirae, respectively. All the studied biological candidates displayed high cell viability inhibition activities against E. coli cell growth. The biofilm inhibition activities of the tested biological candidates were also investigated against S. aureus and P. Aeruginosa. Biological candidates (1-6) can be considered efficient metal nanoparticle-based materials for multi-disciplinary biological applications.

Investigation of the photoconductive properties of thiophene substituted metallo-phthalocyanines.

The synthesis of 4-(thiophen-3-ylethynyl)phthalonitrile was achieved via the Sonogashira cross-coupling reaction. Herein, we report the synthesis of symmetrical metallo-phthalocyanines with cobalt, zinc, and manganese as the metal ions, and tetrakis(ethynylthiophene) groups substituted at the peripheral positions. The new compounds have been characterized by using mass, 1H NMR, 13C NMR, FT-IR and UV-vis spectroscopy. Dark and photoconductivity measurements were carried out on spin coated thiophene substituted metallo-phthalocyanines at various temperatures fixed between 300 and 440 K. Photocurrent generation and charge transport mechanisms are discussed as well. The evaluation of the photoconductive properties of these compounds indicated that the photocurrent generation efficiency and charge transport mechanism exhibited a strong temperature dependence. On the other hand, conductivity measurements revealed that the temperature dependence of the conductivity can be described by the Arrhenius type exponential equation under dark conditions. Furthermore, it was found that the photoconductive behavior of the film can be described successfully by the variable range hopping model for the whole investigated temperature range.