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SER

Structure, Energetics and Reactivity

Catalysis and Fine Chemistry

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The Catalysis & Fine Chemistry (C&FC) laboratory was founded in 2000, by Prof. Mariette M. Pereira and currently integrates the Structure, Energetics and Reactivity Group, directed by Professor Luis G. Arnaut.

At the present, this laboratory is composed of eight full members: the lab coordinator, Mariette M. Pereira (Associate Professor with Habilitation) and eight post-doctoral researchers, besides eight PhD students, two MSc students and one MSc researcher.

The overall goals of the C&FC Lab are focused on the development of sustainable synthetic processes, mainly based on catalytic reactions, aiming at the preparation of value-added products, such as fine chemicals, new hi-tech materials, and compounds for potential use in biological/medical applications.

The C&FC laboratory offers research in classical organic synthesis, organometallic chemistry (vacuum/inert atmosphere line, Schlenck techniques) and high pressure catalytic reactions, being the first and only high pressure carbonylation laboratory in Portugal.

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MAIN GOALS

The scientific interests of C&FC Lab comprise three main areas: Medicinal Chemistry, Materials Chemistry and Coordination Chemistry/Catalysis, strongly intertwined with each other, with sustainable synthesis being at the interface between them.

The research activity of the C&FC Lab has the following major goals:

1) synthesis of tetrapyrrolic macrocycles (porphyrin and phthalocyanine derivatives,) for applications in catalysis (oxidation, carboxylation) and in medicinal chemistry, namely in photodynamic therapy (PDT), photodynamic inactivation (PDI) and medical imaging, such as magnetic resonance imaging (MRI) and positron-emission tomography (PET).

(ii) synthesis of hybrid materials (based on mesoporous silica, carbon nanotubes and magnetic nanoparticles) for different purposes, namely catalysis, environmental remediation and light-driven applications (photocatalysis, non-linear optics and excited state studies).

iii) development of tervalent phosphorus compounds, namely binaphthyl-based phosphite and phosphine ligands, and their transition-metal complexes for application in catalysis: carbonylation, hydroformylation and Tandem reactions, aiming at the synthesis of value added products with potential bioactivity.



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 Research highlights

  • Synthesis/scale-up of NIR photosensitizers (Redaporfin® under clinical trials, World Patent)

  • Sustainable synthetic processes of tetrapyrrolic macrocycles

  • Synthesis of chemical entities for medical imaging (PET, FI, MRI)

  • Development of catalysts/catalytic systems (oxidation, CO2 activation and Tandem carbonylation reactions)

  • Preparation of hybrid material for catalysis and light-driven applications



LAB MEMBERS

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Coordinator: 

Mariette M. Pereira (Associate Professor with habilitation)



Collaborators: 

Prof. Maria José S. M. Moreno (FF-UC) – associated member

Carmen Claver - collaborator

Anna M. Masdeu-Bultó - collaborator



Post-doc Researchers (8):

Mário J. F. Calvete

Sara M. A. Pinto

Rui M. B. Carrilho

César A. Henriques

Gilberto L. B. Aquino

Rita Lopes

Post doc – Project PDI (in admission phase)

Post-doc - Project MATIS (in admission phase)



PhD students (8):

Liliana Damas

Lucas D. Dias

Fábio M. S. Rodrigues

Carolina Vinagreiro

Vanessa Tomé

Rafael Aroso

Giusi Piccirilo

Nídia Maldonado-Carmona (POLYTHEA)



MSc students (2):

Andreia C. S. Gonzalez

Diana Gomes



MSc researcher (1):

Inês Fonseca



Industry Partners

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A. Abrunhosa (ICNAS Produção)

M. Castelo-Branco (ICNAS Produção)

S. Simões (Bluepharma)

C. Silva (Luzitin SA)

D. Gameiro (EuroYser)



International collaborations

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SELECTED PUBLICATIONS (2013-2018)

Papers

2018

- A novel Pd-catalysed sequential carbonylation/cyclization approach toward bis-N-heterocycles: rationalization by electronic structure calculations, Liliana Damas, Rui M. B. Carrilho, Sandra C. C. Nunes, Alberto A. C. C. Pais, László Kollár, Marta Pineiro, Mariette M. Pereira, R. Soc. open sci., 5 (2018), 181140, DOI: 10.1098/rsos.181140 (IF = 2.50]

- Multifunctionalization of cyanuric chloride for the stepwise synthesis of potential multimodal imaging chemical entities, Mário J. F. Calvete, Sara M. A. Pinto, Hugh D. Burrows, M. Margarida C. A. Castro, Carlos F. G. C. Geraldes, Mariette M. Pereira, Arab. J. Chem. (2018), DOI: 10.1016/j.arabjc.2018.06.005. [IF 2.97]

- Dual Rh-Ru catalysts for reductive hydroformylations of olefins to alcohols, Fábio M. S. Rodrigues, Peter K. Kucmierczyk, Marta Pineiro, Ralf Jackstell, Robert Franke, Matthias Beller, Mariette M. Pereira, ChemSusChem (2018), DOI: 10.1002/cssc.201800488. [IF 7.41]

- Hybrid Metalloporphyrin Magnetic Nanoparticles as Catalysts for Sequential Transformation of Alkenes and CO2 into Cyclic Carbonates, Lucas D. Dias, Rui M. B. Carrilho, César A. Henriques, Mário J. F. Calvete, Anna M. Masdeu-Bultó, Carmen Claver, Liane M. Rossi, Mariette M. Pereira, ChemCatChem, 10 (2018) 2792-2803, DOI: 10.1002/cctc.201800397. [IF 4.67]

- Molecular-based selection of porphyrins towards the sensing of explosives in the gas phase, María G. Guillén, Francisco Gámez, Javier Roales, Tânia Lopes-Costa, Sara M. A. Pinto, Mário J. F. Calvete, Mariette M. Pereira, José M. Pedrosa, Sens. Actuators, B: Chem., 260 (2018) 116–124, DOI: 10.1016/j.snb.2017.12.163. [IF 5.68]

- Conjugated macrocyclic materials with photoactivated optical absorption for the control of energy transmission delivered by pulsed radiations, Mário J. F. Calvete, Danilo Dini, J. Photochem. Photobiol. C, 35 (2018) 56-73, DOI: 10.1016/j.jphotochemrev.2018.02.001. [IF = 15.33]

2017

- Solventless Coupling of Epoxides and CO2 in Compressed Medium Catalysed by Fluorinated Metalloporphyrins, Rui M. B. Carrilho, Lucas D. Dias, Raquel Rivas, Mariette M. Pereira, Carmen Claver, Anna M. Masdeu-Bultó, Catalysts, 7 (2017) 210, DOI: 10.3390/catal7070210. [IF 3.47]

- A Cost-Efficient Method for Unsymmetrical Meso-Aryl Porphyrin Synthesis Using NaY Zeolite as an Inorganic Acid Catalyst, Mário J. F. Calvete, Lucas D. Dias, César A. Henriques, Sara M. A. Pinto, Rui M. B. Carrilho, Mariette M. Pereira, Molecules, 22 (2017) 741, DOI: 10.3390/molecules22050741. [IF 3.10]

- Sequential reactions from catalytic hydroformylation toward the synthesis of amino compounds, Ana R. Almeida, Rui M. B. Carrilho, Andreia F. Peixoto, Artur R. Abreu, Artur Silva, Mariette M. Pereira, Tetrahedron, 73 (2017) 2389-2395, DOI: 10.1016/j.tet.2017.03.023. [IF 2.38]

- Ultrafast Dynamics of Manganese(III), Manganese(II), and Free-Base Bacteriochlorin: Is There Time for Photochemistry?, Fábio A. Schaberle, Artur R. Abreu, Nuno P. F. Goncalves, Gonçalo F. F. Sá, Mariette M. Pereira, Luis G. Arnaut, Inorg. Chem., 56 (2017) 2677-2689, DOI: 10.1021/acs.inorgchem.6b0287. [IF 4.70]

- Metal coordinated pyrrole-based macrocycles as contrast agents for magnetic resonance imaging technologies: Synthesis and applications, Mário J. F. Calvete, Sara M. A. Pinto, Mariette M. Pereira, Carlos F. G. C. Geraldes, Coord. Chem. Rev., 333 (2017) 82-107, DOI: 10.1016/j.ccr.2016.11.011. [IF 14.50]

2016

- Cost-efficient method for unsymmetrical meso-aryl porphyrins and iron oxide-porphyrin hybrids prepared thereof, César A. Henriques, Sara M. A. Pinto, João Pina, Carlos Serpa, Auguste Fernandes, Liane M. Rossi, M. Filipa Ribeiro, Mariette M. Pereira, Mário J. F. Calvete, Dalton Trans., 2016, 45, 16211-16220, DOI: 10.1039/c6dt02428a. [IF 4.10]

- Biologically Inspired and Magnetically Recoverable Copper Porphyrinic Catalysts: A Greener Approach for Oxidation of Hydrocarbons with Molecular Oxygen, César A. Henriques, Auguste Fernandes, Liane M. Rossi, M. Filipa Ribeiro, Mário J. F. Calvete, Mariette M. Pereira, Adv. Funct. Mater., 26 (2016) 3359-3368, DOI: 10.1002/adfm.201505405. [IF 13.33]

- Phthalocyanine Labels for Near-Infrared Fluorescence Imaging of Solid Tumors, Ana C. S. Lobo, Alexandre D. Silva, Vanessa A. Tomé, Sara M. A. Pinto, Elsa F. F. Silva, Mário J. F. Calvete, Célia M. F. Gomes, Mariette M. Pereira, Luis G. Arnaut, J. Med. Chem., 59 (2016) 4688-4696, DOI: 10.1021/acs.jmedchem.6b00054. [IF 6.25]

- Highly Efficient Rh(I)/Tris-Binaphthyl Monophosphite Catalysts for Hydroformylation of Sterically Hindered Alkyl Olefins, Gonçalo N. Costa, Rui M. B. Carrilho, Lucas D. Dias, Júlio C. Viana, Gilberto L. B. Aquino, Marta Pineiro, Mariette M. Pereira, J. Mol. Catal. A: Chem., 416 (2016) 73-80, DOI: 10.1016/j.molcata.2016.02.016. [IF 4.40]

- The Quest for Biocompatible Phthalocyanines for Molecular Imaging: Photophysics, Relaxometry and Cytotoxicity Studies, Sara M. A. Pinto, Vanessa A. Tomé, Mário J. F. Calvete, Mariette M. Pereira, Hugh D. Burrows, Ana M. S. Cardoso, Agnés Pallier, M. Margarida C. A. Castro, Éva Toth, Carlos F. G. C. Geraldes, J. Inorg. Biochem., 154 (2016) 50-59, DOI: 10.1016/j.jinorgbio.2015.10.013. [IF 3.06]

- Nonlinear Optical Materials for the Smart Filtering of Optical Radiation, Danilo Dini, Mário J. F. Calvete, Michael Hanack, Chem. Rev., 116 (2016) 13043-13233, DOI: 10.1021/acs.chemrev.6b00033. [IF = 52.61]

2015

- Synthesis of a new 18F labeled porphyrin for potential application in positron emission tomography. In vivo imaging and cellular uptake, Ana V. C. Simões, Sara M. A. Pinto, Mário J. F. Calvete, Célia M. F. Gomes, Nuno C. Ferreira, Miguel Castelo-Branco, Jordi Llop, Antero J. Abrunhosa, Mariette M. Pereira, RSC Adv., 5 (2015) 99540-99546, DOI: 10.1039/c5ra16103g. [IF 2.94]

- (S)-BINOL Immobilized onto Multiwalled Carbon Nanotubes through Covalent Linkage: A New Approach for Hybrid Nanomaterials Characterization, Carlos J. P. Monteiro, Sónia A. C. Carabineiro, Tobias Lauterbach, Christoph Hubbert, A. Stephen K. Ashmi, José. L. Figueiredo Mariette M. Pereira, ChemNanoMat, 1 (2015) 178-187, DOI: 10.1002/cnma.201500028. [IF 3.17]

- Solventless metallation of low melting porphyrins synthesized by the water/microwave method, César A. Henriques, Sara M. A. Pinto, M. Pineiro, João Canotilho, M. Ermelinda Eusébio, Mariette M. Pereira, Mário J. F. Calvete, RSC Adv., 5 (2015) 64916-64924, DOI: 10.1039/c5ra11820d. [IF 2.94]

- One-Step Synthesis of Dicarboxamides via Pd-catalysed Aminocarbonylation using Diamines as N-nucleophiles, Rui M. B. Carrilho, Ana R. Almeida, Mercédesz Kiss, László Kollár, Rita Skoda-Földes, Janusz M. Dabrowski, Maria José S. M. Moreno, Mariette M. Pereira, Eur. J. Org. Chem. (2015) 1840-1847, DOI: 10.1002/ejoc.201403444. [IF 2.88]

- Optical detection of amine vapors using Zn Triad porphyrin thin films, Javier Roales, José M. Pedrosa, María G. Guillén, Tânia Lopes-Costa, Sara M. A. Pinto, Mário J. F. Calvete, Mariette M. Pereira, Sens. Actuators, B: Chem., 210 (2015) 28-35, DOI: 10.1016/j.snb.2014.12.080. [IF 5.67]

2014

- Ecofriendly Porphyrin Synthesis by using Water under Microwave Irradiation, César A. Henriques, Sara M. A. Pinto, Gilberto L. B. Aquino, M. Pineiro, Mário J. F. Calvete, Mariette M. Pereira, ChemSusChem, 7 (2014) 2821-2824, DOI: 10.1002/cssc.201402464. [IF 7.41]

- Highly active phosphite gold (I) catalysts for intramolecular hydroalkoxylation, enyne cyclization and furanyne cyclization, Maria Camila Blanco Jaimes, Frank Rominger, Mariette M. Pereira, Rui M. B. Carrilho, Sónia A. C. Carabineiro, A. Stephen K. Hashmi, Chem. Commun., 50 (2014) 4937-4940, DOI: 10.1039/c4cc00839a. [IF 6.29]

- Size and ability do matter! Influence of acidity and pore size on the synthesis of hindered halogenated meso-phenyl porphyrins catalysed by porous solid oxides, Mónica Silva, Auguste Fernandes, Suse S. Bebiano, Mário J. F. Calvete, M. Filipa Ribeiro, Hugh D. Burrows, Mariette M. Pereira, Chem. Commun., 50 (2014) 6571-6573, DOI: 10.1039/c4cc01100g. [IF 6.29]

- Rhodium-Catalysed Tandem Hydroformylation/Arylation Reaction with Boronic Acids, Ana R. Almeida, Roberto D. Dias, Carlos J. P. Monteiro, Artur R. Abreu, Pedro M. P. Gois, J. Carles Bayon, Mariette M. Pereira, Adv. Synth. Catal., 356 (2014) 1223-1227, DOI: 10.1002/adsc.201300968. [IF 5.12]

- Asymmetric Hydrovinylation and Hydrogenation with Metal Complexes of C3-Symmetric Tris-Binaphtyl Monophosphites, Rui M. B Carrilho, Gonçalo N. Costa, Ângela C. B. Neves, Mariette M. Pereira, Arnald Grabulosa, J. Carles Bayón, Mercè Rocamora, Guillermo Muller, Eur. J. Inorg. Chem. (2014) 1034-1041, DOI: 10.1002/ejic.201301368. [IF 2.51]

2013

- Inorganic helping organic: recent advances in catalytic heterogenous oxidations by immobilised tetrapyrrolic macrocycles in micro and mesoporous supports, Mário J. F. Calvete, Mónica Silva, Mariette M. Pereira, Hugh D. Burrows, RSC Adv. 3 (2013) 22774-22789, DOI: 10.1039/c3ra44038a. [IF 2.94]

- Binol derivative ligand immobilized onto silica: Alkyl-cyanohydrinsynthesis via sequential hydroformylation/heterogeneouscyanosilylation reactions, Mariette M. Pereira, Ângela C. B. Neves, Mário J. F. Calvete, Lucas D. Dias, Auguste Fernandes, Cat. Today, 218-219 (2013) 99-106, DOI: 10.1016/j.cattod.2013.09.050. [IF 4.67]

- Synthesis of binaphthyl based phosphine and phosphite ligands, Mariette M. Pereira, Mário J. F. Calvete, Rui M. B. Carrilho, Artur R. Abreu, Chem. Soc. Rev., 42 (2013) 6990-7027, DOI: 10.1039/c3cs60116a. [IF 40.18]

- A new facile synthesis of steroid dimers containing 17,17’-dicarboxamide spacers, Rui M. B. Carrilho, Mariette M. Pereira, Maria José S. M. Moreno, Attila Takács, László Kollár, Tetrahedron Lett., 54 (2013) 2763-2765, DOI: 10.1016/j.tetlet.2013.02.108. [IF=2.19]

Books/Book chapters

1. Tervalent Phosphorus Acid Derivatives, Mariette M. Pereira, Mário J. F. Calvete, Rui M. B. Carrilho in SPR Organophosphorous Chemistry, Vol 47, D. W. Allen, D. Loakes, J. C. Tebby (Edits.), The Royal Society of Chemistry, Cambridge (2018) pp. 96-156. ISBN: 978-1-78801-167-9; DOI: http://dx.doi.org/10.1039/9781788013055-00096.

Same series since 2015:

2017: DOI: http://dx.doi.org/10.1039/9781788010689-00052.

2016: DOI: http://dx.doi.org/10.1039/9781782626930-00051.

2015: DOI: http://dx.doi.org/10.1039/9781782622765-00056.

2. Applications of Catalytic Hydroformylation in the Synthesis of Biologically Relevant Synthons and Drugs, Mariette M. Pereira in Sustainable Synthesis of Pharmaceuticals: Using Transition Metal Complexes as Catalysts, M. M. Pereira, M. J. F. Calvete (Edits.), The Royal Society of Chemistry, Cambridge (2018) pp. 66-104. ISBN: 978-1-78262-934-4; DOI: http://dx.doi.org/10.1039/9781788010658-00066.

3. Tetrapyrrolic Macrocycles as Molecular Probes for Radionuclide-Based Imaging Techniques, Mário J. F. Calvete, Sara M. A. Pinto, Antero J. Abrunhosa, Mariette M. Pereira in Advances in Medicine and Biology, Vol. 108, L. V. Berhardt (Edit.), Nova Science Publishers, Inc., New York (2017) pp. 217-250. ISBN: 978-1-53610-135-5.

4. Palladium-Catalyzed Asymmetric Transformations of Natural Products and Drug Molecules, Carolina S. Vinagreiro, Fábio M. S. Rodrigues, Rui M. B. Carrilho, Mariette M. Pereira in Asymmetric Synthesis of Drugs and Natural Products, A. Nag (Edit.), CRC Press, Taylor & Francis Ltd., Boca Raton (2017) pp. 293-324. ISBN: 978-1-138-03361-0.

5. Photodynamic Therapy for Cancer Treatment, Luís B. Rocha, L. G. Arnaut, Mariette M. Pereira, L. Almeida, S. Simões in Biomateriais Aplicados ao Desenvolvimento de Sistemas Terapeuticos Avancados, H. C. Sousa, M. E. M. Braga, A. Sosnik (Edits.), Imprensa da Universidade de Coimbra, Coimbra (2015) pp. 637-674. ISBN: 978-989-26-0881-5; DOI: http://dx.doi.org/10.14195/978-989-26-0881-5.

Patents:

Low Molecular Weight Derivatives of Carboxamide Halogenated porphyrins, namely Chlorins and Bacteriochlorins, and their Apllications Thereof, G. P. N. Costa, N. P. F. Gonçalves, C. J. P. Monteiro, A. C. R. Abreu, H. T. F. C. Soares, L. G. B. Rocha, F. A. Schaberle, M. M. Pereira, L. G. Arnaut, Patente Europeia EP3292129, 2018.

Atropoisomers of Halogenated Tetraphenylbacteriochlorins and Chlorins and their use in Photodynamic Therapy, N. P. F. Gonçalves, T. P. C. M. dos Santos, G. P. N. Costa, C. J. P. Monteiro, F. A. Schaberle, S. C. Alfar, A. C. R. Abreu, M. M. Pereira, L. G. Arnaut, Luzitin SA, Universidade de Coimbra, Patente Mundial WO/2016/151458 A1, 2016.