Photooxidation of anthracene under visible light with metallocarboxyphenylporphyrins


  • Carlos Enrique Díaz-Uribe Universidad del Atlántico
  • William Andrés Vallejo-Lozada Universidad del Atlántico
  • Fernando Martínez-Ortega Universidad Industrial de Santander


Porphyrin, singlet oxygen, anthracene, TEMPO


In this work, three novel carboxyphenylporphyrins (TcPP-M, M= H, Cu y Zn) have been synthesized and their efficiency in the photooxidation of anthracene under visible light (l> 500 nm) through generation of oxygen singlet (1O2) has been evaluated. The presence of 1O2 was evidenced by Electron Paramagnetic Resonance (EPR), where  it reacts with 2,2,6,6-tetramethyl-4-piperidone-N (TEMP) to produce 2,2,6,6-tetramethyl-4-piperidone-N-oxyl radical (TEMPO). The catalytic results indicated that the incorporation of the metal in the porphyrin ring strongly affects their efficiency on the anthracene oxidation. The TcPPH showed a higher photonic efficiency (31%) in the anthracene conversion than TcPPZn (13%) and TcPPCu (9%). This result may be related to the disruption of the planarity of the porphyrin ring. Finally the formation of anthraquinone and oxanthrone was detected as the oxidation products in the anthracene oxidation with 1O2.

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Author Biographies

Carlos Enrique Díaz-Uribe, Universidad del Atlántico

PhD in Chemistry-UIS

Assistant Professor, Faculty of Basic Sciences, Chemistry Program

Research Group in Photochemistry and Photobiology

William Andrés Vallejo-Lozada, Universidad del Atlántico

Research Group in Photochemistry and Photobiology, Faculty of Basic Sciences, Professor

Fernando Martínez-Ortega, Universidad Industrial de Santander

Center for Research in Catalysis, School of Chemistry


C. Geng, J. Chen, X. Yang, L. Ren, B. Yin, X. Liu, Z. Baid. “Emission factors of polycyclic aromatic hydrocarbons from domestic coal combustion in China”. J. Environ. Sci. Vol. 26. 2014. pp. 160-166.

L. Siddens, A. Larkin, S. Krueger, C. Bradfield, K. Waters, S. Tilton, C. Pereira, C. Löhr, V. Arlt, D. Phillips, D. Williams, W. Baird. “Polycyclic aromatic hydrocarbons as skin carcinogens: Comparison of benzo[a]pyrene, dibenzo[def,p]chrysene and three environmental mixtures in the FVB/N mouse”. Toxicol. Appl. Pharm. Vol. 264. 2012. pp. 377-386.

C. Diaz, F. León, M. Daza, F. Martínez. “Oxidation of anthracene with singlet oxygen generated chemically by the sodium molibdate/hydrogen peroxide system”. Rev. Colomb. Quim. Vol. 37. pp. 45-53.

F. Goulay, C. Rebrion, J. Le Garrec, S. Le Picard, A. Casona, B. Rowe. “The reaction of anthracene with OH radicals: An experimental study of the kinetics between 58 and 470 K”. J. Phys. Chem. Vol. 122. 2005. pp. 1-7.

C. Hofelt, M. Honeycutt, J. McCoy, L. Haws. “Development of a Metabolism Factor for Polycyclic Aromatic Hydrocarbons for Use in Multipathway Risk Assessments of Hazardous Waste Combustion Facilities”. Regul. Toxicol. Pharm. Vol. 33. 2001. pp. 60-65.

J. Aubry, C. Pierlot, J. Rigaudy, R. Schmidt. “Reversible binding of oxygen to aromatic compounds”. Acc. Chem. Res. Vol. 36. 2003. pp. 668-675.

M. Kreitner, R. Ebermann, G. Alth. “Quantitative determination of singlet oxygen production byporphyrins”. J. Photochem. Photobiol. B: Biol. Vol. 36. 1996. pp. 109-111.

C. Tanielian, C. Wolff. “Porphyrin-sensitized generation of singlet molecular Oxygen: comparison of steady-state and time-resolved methods”. J. Phys. Chem. Vol. 99. 1995. pp. 9825-9830.

B. Cohen, M. Bergkvist. “Targeted in vitro photodynamic therapy via aptamer-labeled, porphyrinloaded virus capsids”. J. Photochem. Photobiol. B: Biol. Vol. 121. 2013. pp. 67-74.

S. Banfi, E. Caruso, L. Buccafurni, V. Battini, S. Zazzaron, P. Barbieri, V. Orlandi. “Antibacterial activity of tetraaryl-porphyrin photosensitizers: An in vitro study on Gram negative and Gram positive bacteria”. J. Photochem. Photobiol. B: Biol. Vol. 85. 2006. pp. 28-38.

G. Granados, E. Páez, F. Martínez, M. Piccinato, F. Silva, C. Barbosa, E. Di Mauro, M. da Costa, A. Tsutomu. “Visible light production of superoxide anion with MCarboxyphenylporphyrins (M=H, Fe, Co, Ni, Cu, and Zn) free and anchored on TiO2 : EPR characterization”. J. Mol. Catal. A: Chem. Vol. 339. 2011. pp. 79-85.

C. Diaz, M. Daza, E. Páez, F. Martínez, C. Guedes, E. Di Mauro. “Visible light singlet oxygen production with tetra(4-carboxyphenyl)porphyrin/SiO2 ”. J. Photochem. Photobiol. A: Chem. Vol. 259. 2013. pp. 47-52.

G. Granados, E. Páez, F. Ortega, C. Ferronato, J. Chovelon. “Degradation of atrazine using metalloporphyrins supported on TiO2 under visible light irradiation”. Appl. Catal. B: Environ. Vol. 89. 2009. pp. 448-454.

J. Cornet, A. Marty, J. Gros. “Revised technique for the determination of mean incident light fluxes on photobioreactors”. Biotechnol. Prog. Vol. 13. 1977. pp. 408-415.

C. Schweitzer, R. Schmidt. “Physical mechanisms of generation and deactivation of singlet oxygen”. Chem. Rev. Vol. 103. 2013. pp. 1685-1757.

J. Marugán, D. Hufschmidt, M. López. “Photonic efficiency for methanol photooxidation and hydroxyl radical generation on silica-supported TiO2 photocatalysts”. Appl. Catal. B: Environ. Vol. 62. 2006. pp. 201-207.

S. Mathai, T. Smith, K. Ghiggino. “Singlet oxygen quantum yields of potential porphyrinbased photosensitisers for photodynamic therapy”. Photochem. Photobiol. Sci. Vol. 6. 2007. pp. 995-1002.

G. Cauzzo, G. Gennari, G. Jori, J. Spikes. “The effect of chemical structure on the photosensitizing efficiencies of porphyrins”. Photochem. Photobiol. Vol. 25. 1997. pp. 389-395.

Y. Lion, M. Delmelle, A. van de Vorst. “New method of detecting singlet oxygen production”. Nature. Vol. 263. 1976. pp. 442-443.

C. Hadjur, A. Jeunet, P. Jardon. “Photosensitization by hypericin: electron spin resonance (ESR) evidence for the formation of singlet oxygen and superoxide anion radicals in an in vitro model”. J. Photochem. Photobiol. B: Biol. Vol. 26. 1994. pp. 67-74.



How to Cite

Díaz-Uribe, C. E., Vallejo-Lozada, W. A., & Martínez-Ortega, F. (2014). Photooxidation of anthracene under visible light with metallocarboxyphenylporphyrins. Revista Facultad De Ingeniería Universidad De Antioquia, (73), 225–233. Retrieved from