Gadolinium mono and bisphthalocyanine obtained in a single synthesis and their bactericidal activity
DOI:
https://doi.org/10.34117/bjdv12n2-006Keywords:
gadolinium bisphthalocyanine, phthalocyanine, synthesis, bactericidal activityAbstract
Phthalocyanines can be prepared in different forms. The synthesis using lanthanides metals, in general, results in bisphthalocyanines molecules, while synthesis with transitions metals can produce monophthalocyanine, simple called phthalocyanines. To obtain one or another form of the compounds it is necessary to carry out more than one synthesis, using small differences in the temperature. In this paper we reported, for the first time, a synthesis where could be obtained a compound containing both forms of gadolinium, mono (GdPc) and bisphthalocyanine (GdPc2). Different forms were separated and characterized by spectroscopy methods (absorption and infrared). The obtained forms were tested for antibacterial activities using the Pseudomonas aeruginosa in agar diffusion method and broth dilution assays, showed that only GdPc2 presented activity aganst this bacteria.
References
AI, X.; LIN, J.; CHANG, Y.; ZHOU, L. et al. Phase modification of copper phthalocyanine semiconductor by converting powder to thin film. Applied Surface Science, 428, p. 788–792, 2018/01/15/ 2018.
ARRIETA, A.; RODRIGUEZ-MENDEZ, M. L.; DE SAJA, J. A. Langmuir-Blodgett film and carbon paste electrodes based on phthalocyanines as sensing units for taste. Sensor Actuat. B-Chem., 95, n. 1-3, p. 357–365, Oct 2003. Article; Proceedings Paper.
BALOUIRI, M.; SADIKI, M.; IBNSOUDA, S. K. Methods for in vitro evaluating antimicrobial activity: A review. J. Pharm. Anal., 6, n. 2, p. 71–79, 2016/04/01/ 2016.
BARARD, S.; KREOUZIS, T.; CAMMIDGE, A. N.; COOK, M. J. et al. Newly synthesised gadolinium bisphthalocyanine sandwich complex: ambipolar organic semiconductor. Semicond. Sci. Tech., 33, n. 9, p. 095010–095011–095010–095017, Sep 2018.
CLARISSE, C.; RIOU, M. T. SYNTHESIS AND CHARACTERIZATION OF SOME LANTHANIDE PHTHALOCYANINES. Inorg. Chim. Acta 130, n. 1, p. 139–144, Jun 1987.
DE BONI, L.; GAFFO, L.; MISOGUTI, L.; MENDONCA, C. R. Nonlinear absorption spectrum of ytterbium bis-phthalocyanine solution measured by white-light continuum Z-scan technique. Chem. Phys. Lett., 419, n. 4-6, p. 417–420, Feb 2006.
DE BONI, L.; PIOVESAN, E.; GAFFO, L.; MENDONCA, C. R. Resonant nonlinear absorption in Zn-phthalocyanines. J. Phys. Chem. A 112, n. 30, p. 6803–6807, Jul 2008. Letter.
DEDKOVA, K.; KUZNIKOVA, L.; PAVELEK, L.; MATEJOVA, K. et al. Daylight induced antibacterial activity of gadolinium oxide, samarium oxide and erbium oxide nanoparticles and their aquatic toxicity. Materials Chemistry and Physics, 197, p. 226–235, Aug 2017.
EL-NAHASS, M. M.; SOLIMAN, H. S.; KHALIFA, B. A.; SOLIMAN, I. M. Structural and optical properties of nanocrystalline aluminum phthalocyanine chloride thin films. Mat. Sci. Semicon. Proc., 38, p. 177–183, Oct 2015.
FURINI, L. N.; FEITOSA, E.; ALESSIO, P.; SHIMABUKURO, M. H. et al. Tuning the nanostructure of DODAB/nickel tetrasulfonated phthalocyanine bilayers in LbL films. Mat. Sci. Eng. C-Mater., 33, n. 5, p. 2937–2946, Jul 2013. Article.
GAFFO, L.; GONCALVES, D.; DHANABALAN, A.; MOREIRA, W. C. et al. Electrochromic and redox properties of Langmuir-Blodgett films of ytterbium bisphthalocyanine. Synthetic Met., 124, n. 2-3, p. 351–356, Oct 2001.
GAFFO, L.; ZUCOLOTTO, V.; CORDEIRO, M. R.; MOREIRA, W. C. et al. Structural aspects of Langmuir–Blodgett and cast films of zinc phthalocyanine and zinc hexadecafluorophthalocyanine. Thin Solid Films, 515, n. 18, p. 7307–7312, 2007/06/25/ 2007.
GARCIA-HERNANDEZ, C.; MEDINA-PLAZA, C.; GARCIA-CABEZON, C.; MARTIN-PEDROSA, F. et al. An Electrochemical Quartz Crystal Microbalance Multisensor System Based on Phthalocyanine Nanostructured Films: Discrimination of Musts. Sensors, 15, n. 11, p. 29233–29249, Nov 2015. Article.
GONIDEC, M.; DAVIES, E. S.; MCMASTER, J.; AMABILINO, D. B. et al. Probing the Magnetic Properties of Three Interconvertible Redox States of a Single-Molecule Magnet with Magnetic Circular Dichroism Spectroscopy. J. Am. Chem. Soc., 132, n. 6, p. 1756–+, Feb 2010.
GSANGER, M.; BIALAS, D.; HUANG, L. Z.; STOLTE, M. et al. Organic Semiconductors based on Dyes and Color Pigments. Adv. Mat., 28, n. 19, p. 3615–3645, May 2016. Review.
KADISH, K. M., SMITH, K. M., GUILARD, R. Phthalocyanines: Properties and Materials. In: The Porphyrin Handbook. San Diego, California, USA: ACADEMIC PRESS, 2003. v. 17.
KARADOGAN, B.; KILICARSLAN, F. A.; ERDEN, I. Synthesis of phthalocyanines with donor-acceptor properties and their applications to dye-sensitized solar cell. Chemical Papers, 73, n. 9, p. 2283–2288, Sep 2019.
KHADAR, Y. A. S.; BALAMURUGAN, A.; DEVARAJAN, V. P.; SUBRAMANIAN, R. Hydrothermal Synthesis of Gadolinium (Gd) Doped Cerium Oxide (CeO2) Nanoparticles: Characterization and Antibacterial Activity. Orient. J. Chem., 33, n. 5, p. 2405–2411, Oct 2017.
KIRIN, I. S.; MOSKALEV, P. N.; MISHIN, V. Y. SYNTHESIS OF PHTHALOCYANINES OF SOME HEAVY METALS. J. Gen. Chem. USSR, 37, n. 1, p. 265–&, 1967.
KRATOCHVILOVA, I.; SEBERA, J.; PARUZEL, B.; PFLEGER, J. et al. Electronic functionality of Gd-bisphthalocyanine: Charge carrier concentration, charge mobility, and influence of local magnetic field. Synthetic Metals, 236, p. 68–78, Feb 2018.
KUMAR, G. A.; NAIK, H. S. B.; VISWANATH, R.; GOWDA, I. K. S. et al. Tunable emission property of biotin capped Gd:ZnS nanoparticles and their antibacterial activity. Mat. Sci. Semicon. Proc., 58, p. 22–29, Feb 2017.
LI, X.; ZHENG, B.-D.; PENG, X.-H.; LI, S.-Z. et al. Phthalocyanines as medicinal photosensitizers: Developments in the last five years. Coordin. Chem. Rev., 379, p. 147–160, 2019/01/15/ 2019.
LIU, T.; ZHANG, F.; RUAN, L.; TONG, J. et al. Facile synthesis and characterization of crystalline iron phthalocyanine. Materials Letters, 237, p. 319–322, 2019/02/15/ 2019.
MACHADO, A. E. D. Photodynamic therapy: Principles, potential of application and perspectives. Quim. Nova, 23, n. 2, p. 237–243, Mar–Apr 2000. Article.
MARTIN, M. G.; DE SAJA, J. A.; MUNOZ, R.; RODRIGUEZ-MENDEZ, M. L. Multisensor system based on bisphthalocyanine nanowires for the detection of antioxidants. Electrochim. Acta, 68, p. 88–94, Apr 2012. Article.
MOREIRA, L. M.; DOS SANTOS, F. V.; LYON, J. P.; MAFTOUM-COSTA, M. et al. Photodynamic therapy: Porphyrins and phthalocyanines as Photosensitizers. Aust. J. Chem., 61, n. 10, p. 741–754, 2008. Review.
OSIFEKO, O. L.; DURMUS, M.; NYOKONG, T. Physicochemical and photodynamic antimicrobial chemotherapy studies of mono- and tetra-pyridyloxy substituted indium(III) phthalocyanines. J. Photoch. Photobio. A, 301, p. 47–54, Mar 2015. Article.
PALACIN, S. Phthalocyanines in Langmuir and Langmuir-Blodgett films: from molecular design to supramolecular architecture. Adv. Colloid Interfac., 87, n. 2-3, p. 165–181, Nov 2000. Article.
POSS, M.; ZITTEL, E.; SEIDL, C.; MESCHKOV, A. et al. Gd-4(3+) AlPCS4 (3)(4-) Nanoagent Generating O-1(2) for Photodynamic Therapy. Advanced Functional Materials, 28, n. 32, Aug 2018.
RAY, A. K.; EXLEY, J.; GHASSEMLOOY, Z.; CROWTHER, D. et al. Optical absorption in metal bisphthalocyanine sublimed films. Vacuum, 61, n. 1, p. 19–27, Apr 2001. Article.
RIBEIRO, J. N.; FLORES, A. V.; MESQUITA, R. C.; NICOLA, J. H. et al. Terapia Fotodinâmica: uma luz na luta contra o câncer. Physicae, p. 5–14 ISSN 22363521, 2005–01–01 2005.
RICHARDSON, T.; SMITH, V. C.; TOPACLI, A.; JIANG, J. et al. In situ visible spectroscopy of a gadolinium bisphthalocyanine LB film exposed to chlorine gas. Supramol. Sci. , 4, n. 3-4, p. 465–470, Sep–Dec 1997. Article; Proceedings Paper.
RODRIGUEZ-ME´NDEZ, M. L.; GOBERNADO-MITRE, M. I.; SOUTO, J.; DE SAJA-GONZA´LEZ, J. et al. Response of chemically modified PrPc2, PrPc2 and GdPc2 Langmuir-Blodgett films to tobacco smoke. Sensor Actuat. B-Chem., 25, n. 1–3, p. 643–646, 4// 1995.
RODRIGUEZ-MENDEZ, M. L.; GARCIA-HERNANDEZ, C.; MEDINA-PLAZA, C.; GARCIA-CABEZON, C. et al. Multisensor systems based on phthalocyanines for monitoring the quality of grapes. J. Porphyr. Phthalocya., 20, n. 8-11, p. 889–894, Aug–Nov 2016. Article.
SARKODIE, B.; ACHEAMPONG, C.; ASINYO, B.; ZHANG, X. et al. Characteristics of pigments, modification, and their functionalities. Color Res. Appl., 44, n. 3, p. 396–410, Jun 2019.
VIVAS, M. G.; DE BONI, L.; GAFFO, L.; MENDONCA, C. R. Investigation of ground and excited state photophysical properties of gadolinium phthalocyanine. Dyes Pigments, 101, p. 338–343, Feb 2014. Article.
WANG, H. L.; WANG, B. W.; BIAN, Y. Z.; GAO, S. et al. Single-molecule magnetism of tetrapyrrole lanthanide compounds with sandwich multiple-decker structures. Coordin. Chem. Rev., 306, p. 195–216, Jan 2016.
