RESUMEN

The synthesis of two novel phthalonitrile derivatives (3-4) bearing ethynylcyclohex-1-ene and ethynylcyclohexane groups and two peripherally octa substituted zinc (II) phthalocyanines (5-6) were prepared. The synthesis of phthalonitrile derivatives was performed with Sonagashira coupling reaction by using palladium-catalyzed. The newly synthesized compounds were characterized by using FT-IR, NMR, mass, and UV-Vis absorption spectroscopy techniques. Aggregation studies of 5 and 6 were performed in various organic solvents and different concentrations in tetrahydrofuran (THF). The photophysical studies of the Pcs were performed in THF to determine the effect of the alkyne groups on the fluorescence of the Pc ring. Substances showing fluorescence properties can be used in practical applications such as to create an image in microscopy. Fluorescence quantum yield (ΦF) and fluorescence lifetime (τF) of 5-6 were calculated. The fluorescence quenching studies of 5-6 were performed by adding the different concentrations of 1,4-benzoquinone (BQ) to a constant concentration of the Pcs in THF and it was found that benzoquinone was an effective quencher. The values of the Stern-Volmer constant (Ksv) and quenching constant (kq) of zinc phthalocyanines (5-6) were examined. All obtained results were compared with each other and with unsubstituted zinc Pc compound used as a reference.

RESUMEN

In this study, a new fluorinated phthalonitrile compound namely 5-bis[4-(trifluoromethoxy)-thiophenyl] phthalonitrile was synthesized. In addition, peripherally substituted symmetric metallated phthalocyanine derivatives [M = Co (2) and M = Zn (3)] and unsymmetrically substituted zinc phthalocyanine (ZnPc) complex (4) were synthesized by cyclotetramerization of this phthalonitrile compound. Characterization of all new compounds was carried out using FT-IR, NMR, UV-Vis, and mass spectroscopy. Additionally, antioxidant activity, DNA cleavage activity, antimicrobial activity, biofilm inhibition activity, and bacterial viability inhibition test of the compounds (1-4) were investigated. The antioxidant activities of the new phthalocyanine complexes were studied by performing two different methods. The results indicated that the highest DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging activity was determined to be 67.85% for 2 and also 3 showed the highest activity with 31.65% for chelating activity at 200 mg L-1 concentration. Phthalocyanine compounds demonstrated effective DNA cleavage and antimicrobial activities. The highest percentage of cell vitality inhibition was found for compound 4, 56.92%. Also, test compounds exhibited good biofilm inhibition activity.

Asunto(s)

Antiinfecciosos , Antioxidantes , Quelantes , Cobalto , Flúor , Isoindoles , Compuestos Organometálicos , Compuestos de Zinc , Antiinfecciosos/química , Antiinfecciosos/farmacología , Antioxidantes/química , Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Bacterias/genética , Biopelículas/efectos de los fármacos , Compuestos de Bifenilo/química , Candida albicans/efectos de los fármacos , Candida albicans/crecimiento & desarrollo , Quelantes/química , Quelantes/farmacología , Cobalto/química , Cobalto/farmacología , División del ADN , Flúor/química , Flúor/farmacología , Hierro/química , Isoindoles/química , Isoindoles/farmacología , Compuestos Organometálicos/química , Compuestos Organometálicos/farmacología , Picratos/química , Compuestos de Zinc/química , Compuestos de Zinc/farmacología

RESUMEN

Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

Asunto(s)

Indoles/química , Técnicas de Química Sintética , Electroquímica , Indoles/síntesis química , Isoindoles , Metales/química , Procesos Fotoquímicos , Análisis Espectral

RESUMEN

Due to their flexibility and solution applicability, organic field-effect transistors (OFETs) are considered prominent candidates for application in flexible and low-cost devices. A soluble phthalocyaninato cobalt(ii) complex was designed and synthesized based on a hexadeca-substitution pattern by introducing peripheral phenylethynyl groups and non-peripheral n-butoxy groups. The cobalt phthalocyanine derivative was characterized using a wide range of spectroscopic and electrochemical methods, as well as single-crystal X-ray diffraction analysis. An OFET device was fabricated using a spin-coated film of soluble 1,4,8,11,15,18,22,25-octakisbutoxy-2,3,9,10,16,17,23,24-octakis-ethynyl phenyl phthalocyaninato cobalt(ii) with a bottom-gate top-contact device configuration. The transfer and output characteristics were investigated to evaluate the charge carrier mobility. The mechanisms of the leakage current through the gate dielectric were also investigated, which revealed that the dominant leakage current mechanism is Fowler-Nordheim tunneling.