>PORPHYRINS AND CHLORINS

Porphyrins and chlorins are tetrapyrrole macrocycles that have their place in the ubiquitous class of natural pigments so important for life on earth. Porphyrins, for instance, are found in the red pigment of blood as an iron complex of protoporphyrin IX, while chlorins containing magnesium as the central metal are the green pigments of plants and bacterial photosynthesis. As both natural porphyrinoid molecules are extremely unstable and difficult to handle, the preparation of synthetic analogues has been explored as a very attractive approach, while strong efforts are being made to perform more sustainable and environmentally friendly reactions using often innovative heating techniques.

The research group has been focused in carrying functionalities at the periphery of the porphyrinoid molecules and explore the coordination properties with metal ions, in order to improve their physicochemical properties. We evaluate the structural features of the molecules, their photophysical and chemical properties, using several spectroscopic methods.

>REPRESENTATIVE PUBLICATIONS

 

Ohmic heating-assisted synthesis and characterization of Zn(II), Cu(II) and Pd(II) complexes of heterocyclic–fused chlorins, Maria I. F. Moreira, José Almeida, Andreia Leite, Ana I. M. C. Lobo Ferreira, Luís M. N. B. F. Santos, Ana M. G. Silva and Maria Rangel, Dalton Transactions, 2022, 51, 3520–3530.

 

Synthesis of a highly emissive carboxylated pyrrolidine-fused chlorin for optical sensing of TATP vapours, Alejandro P. Vargas, José Almeida, Francisco Gámez, Javier Roales, Carla Queirós, Maria Rangel, Tânia Lopes-Costa, Ana M. G. Silva and José M. Pedrosa, Dyes Pigm. 2021, 195, 109721;

 

Synthesis, characterization, and cellular investigations of porphyrin– and chlorin–indomethacin conjugates for photodynamic therapy of cancer, José Almeida, Guanyu Zhang, Maodie Wang, Carla Queirós, Ana F. R. Cerqueira, Augusto C. Tomé, Giampaolo Barone, M. Graça H. Vicente, Evamarie Hey-Hawkins, Ana M. G. Silva and Maria Rangel, Org. Biomol. Chem. 2021, 19, 6501.

 

(Aminophenyl)porphyrins as precursors for the synthesis of porphyrin-modified siloxanes. José Almeida, Maria E. Fortună, Lucia Pricop, Andrei Lobiuc, Andreia Leite, André M. N. Silva, Rodrigo P. Monteiro, Maria Rangel, Valeria Harabagiu and Ana M. G. Silva, J. Porphyrins Phthalocyanines 2019, 23, 1001–1012. https://doi.org/10.1142/S1088424619500573.

 

Synthesis and coordination studies of 5-(4′-carboxyphenyl)-10,15,20-tris(pentafluorophenyl)porphyrin and its pyrrolidine-fused chlorin derivative, José Almeida, André M. N. Silva, Susana L. H. Rebelo, Luís Cunha-Silva, Maria Rangel, Baltazar de Castro, Andreia Leite and Ana M. G. Silva, New J. Chem. 2018, 42, 8169-8179. http://dx.doi.org/10.1039/C7NJ05165D.