Exploring the Unique Properties of Designed Porphyrins and Phthalocyanines

The design and synthesis of novel porphyrins (Pors) and phthalocyanines (Pcs) for different applications have been an extremely hot area. The possibility of mimic most of the vital functions of the natural porphyrin derivatives, make this type of compounds unique in many scientific and technological areas, especially when combined with light.¹ The possibility of decorate the periphery of their cores with different motifs and select their central metals, allow to fine-tune the physico-chemical properties/functionalities of novel molecules/materials to be used in these areas.¹

In collaboration with colleagues from complementary areas, we have successfully been designing, synthesizing and evaluate several of these dyes in: i) photomedicine, acting as singlet oxygen generators, especially in cancer photodynamic therapy (PDT)² and in (multi)resistant pathogenic microorganisms photodynamic inactivation (PDI);³ ii) optical (chemo)sensors, to detect, trap and/or degrade pollutants from contaminated environments, such as anionic⁴ and nitro aromatic compounds;⁵ iii) (photo)catalysts, to be used in industrial and environmental applications;⁶ and iv) the construction of several other functional materials, especially when combined with nanostructures.⁷In this communication, it will be highlighted some of our recent works, presenting the used synthetic strategies and the obtained results in the indicated applications.

 

Achnowledgements:Thanks are due to the Universities of Aveiro and Ghent, FCT (Portugal) and FEDER for funding the projects PTDC/QUI/65228/2006 and PTDC/CTM/101538/2008; CNPq (Brazil) for funding the program “Ciência sem Fronteiras/2012” (4802069445108663); and to the European Commission for the Marie Curie Initial Training Network FP7-PEOPLE-2012-ITN/316975.

References:

1. a) Handbook of Porphyrin Science, K. Kadish, K. M. Smith, R. Guilard, Eds., World Scientific Publisher, Singapore, 2010-2013, vol. 1-25; b) R. Bonnett, Chemical Aspects of Photodynamic Therapy, Gordon and Breach Science Publishers, London, 2000; c) Cavaleiro, J. A. S.; Faustino, M. A. F.; Tome, J. P. C., “Porphyrinyl-type sugar derivatives: synthesis and biological applications”, in Carbohydrate Chemistry, Rauter, A. P.; Lindhorst, T., Eds., Royal Society of Chemistry, 2009, 35, 199-231.
2. a) Leandro M. O. Lourenço et al. Dalton Transactions, 2014, accepted; b) Leandro M.O. Lourenço et al. Chem. Commun., 2014, 50, 8363-8366; c) Patrícia M.R Pereira et al. PLOS ONE, 2014, 9 (4), e95529; d) Patrícia M.R Pereira et al. Org. Biomol. Chem., 2014, 12, 1804-1811; e) Sandrina Silva et al. Chem. Commun., 2012, 48 (30), 3608–3610.
3. a) Joana Almeida et al. Photochem. Photobiol. Sci., 2014, 13 (4), 626–633; b) Eliana Alves et al. Future Med. Chem., 2014, 6 (2), 141-64; c) Clara F.A.C. Gomes et al. Photochem. Photobiol. Sci., 2013, 12, 262-271; d) Dora C.S. Costa et al. Photochem. Photobiol. Sci., 2012, 11, 1905-1913; e) Joana B. Pereira at al. Photochem. Photobiol., 2012, 88 (3), 537-547; f) João P.C. Tomé et al. patents nºs 102572(S) and 102581(T).
4. a) João M.M. Rodrigues et al. Chem. Commun., 2014, 50, 1359-1361; b) Andreia S. F. Farinha et al. Sensors & Actuators: B. Chem., 2014, 201, 387-394; c) Luis B. Melo et al. Optical Fiber Technology, 2014, 20 (4), 422-427.
5. a) N. Venkatramaiah et al. J. Mater. Chem. C, 2014, accepted; b) Venkatramaiah et al. Chem. Commun., 2014, 50, 9683-9686;
6. a) Sérgio M. F. Vilela et al. Chem. Commun., 2013, 49, 6400-6402; b) Filipe A. Almeida Paz et al. Chem. Soc. Rev., 2012, 41 (3), 1088-1110; e) Ana M.V.M. Pereira et al. Chem. Eur. J., 2012, 18 (11), 3210-3219; f) Alessandro Varotto et al. J. Am. Chem. Soc. 2010, 132 (8), 2552–2554.
7. a) Eliana Alves et al. Dyes Pigments, 2014, 110, 80-88; b) Carla M.B. Carvalho et al. ACSNano, 2010, 4 (12), 7133-7140; c) João P.C. Tomé et al. patent nº 103828.