Faculdade

Departamento

António Jorge Dias Parola

Associate Professor with Aggregation
Secção de Química
402
(+351) 212948300
10923
(+351) 212948550

Research Interests

Scientific Area: Chemical synthesis, Photochemistry, Supramolecular chemistry

Research Interests
Supramolecular Photochemistry: from the design and synthesis of supramolecular species to the study of their photophysical properties.
After a Ph.D. in photochemistry of host-guest supramolecular assemblies and a post-doc on organic and inorganic synthesis, the following research topics hold:
i) synthesis of flavylium salts with different substitution patterns and their characterization in solution and upon encapsulation by micelles, gels, polymers, zeolites.
ii) photochemical study of the sensor ability of fluorescent polyamine systems towards anions and metal cations.
iii) development of chromogenic materials for applications. Integration of photochromic (flavylium-related), thermochromic and electrochromic molecular systems in functional materials.
iv) synthesis of building blocks for photoactive molecular cages.

After a degree in Applied Chemistry (specialization in Organic Chemistry), my research background, dating back from my PhD thesis in Physical Chemistry (“Supramolecular Photochemistry: Supracomplexes and Hemicarceplexes”, FCT-UNL, Fernando Pina), lays on two main areas: (i) chemical synthesis, including both organic and inorganic synthesis, and (ii) photochemistry. A post-doc in inorganic synthesis of fluorescent metal complexes of polypiridine receptors reinforced this background (Switzerland, Peter Belser). Supramolecular photochemistry, from the design and synthesis of supramolecular species to the study of their photophysical properties, adequately coins this research area that menained until today. My current research further includes (i) development of multiresponsive molecular networks based on flavylium dyes both in solution and upon encapsulation in several hosts and matrices; (ii) the development of chromogenic materials for technological apllications (mainly photochromic). Main methodologies used: standard synthetic methods, strong NMR characterization, continuous photochemical irradiation, steady-state and time-resolved UV-Vis-NIR absorption and emission spectroscopies, flash-photolysis, stopped-flow, electrochemistry.
My main scientific achievements relate with the synthesis and photochemical characterisation of host-guest systems. A collaboration with the YDreams company, started some years ago, led to the creation in 2010 of Ynvisible, a spin-off on chromogenic materials.
Major funding for research raised from FCT-MCE (3 projects as PI), QREN technological projects and EU COST and FP7 projects (as participant). 

Main Publications

A. M. Diniz, C. Pinheiro, V. Petrov, A. J. Parola, F. Pina
“Synthesis and Characterization of a Symmetric Bis-7-hydroxyflavylium Containing a Methyl Viologen Bridge.”
Chem. Eur. J., 2011, 17, 6359-6368

M. G. Ventura, A. J. Parola, A. Pires de Matos
“Influence of heat treatment on the colour of Au and Ag glasses produced by the sol–gel pathway”
J. Non-Cryst. Solids, 2011, 357, 1342-1349

Y. Leydet, A. J. Parola, F. Pina
“Hydroxypyrydinechromene and Pyridinechalcone: Two Coupled Photochromic Systems.”
Chem. Eur. J., 2010, 16, 545–555

R. Gomes, A. J. Parola, F. Bastkowski, J. Polkowska, F.-G. Klärner
“Host-guest interactions between molecular clips and multistate systems based on flavylium salts”
J. Am. Chem. Soc., 2009, 131, 8922–8938

A. M. Diniz, R. Gomes, A. J. Parola, C. A. T. Laia, F. Pina
“Photochemistry of 7-hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium and related compounds”
J. Phys. Chem. B, 2009, 113(3), 719–727

L. Rodríguez, E. Garcia-España, J. C. Lima, A. J. Parola, F. Pina, J. M. Llinares, C. Soriano, J. Alarcón, R. Aucejo
“Anion Detection by Fluorescent Zn(II) Complexes of Functionalized Polyamine Ligands”
Inorg. Chem., 2008, 47(14), 6173-6183

M. M. Sousa, M. J. Melo, A. J. Parola, P. J. T. Morris, H. S. Rzepa, J. S. Seixas de Melo
“A study in Mauve: Unveiling Perkin’s Dye in Historic Samples”
Chem. Eur. J., 2008, 14, 8507-8513

C. Pinheiro, A. J. Parola, F. Pina, J. Fonseca, C. Freire
“Electrocolorimetry of electrochromic materials on flexible ITO electrodes”
Sol. Energy Mater. Sol. Cells, 2008, 92, 980-965

R. Gomes, A. J. Parola, C. Laia, F. Pina
“Promoting Photochromism on Flavylium Derived 2-Hydroxychalcones in Aqueous Solutions by Addition of CTAB Micelles”
J. Phys. Chem. B, 2007, 111, 12059-12065

C. Baptista, J. C. Lima, A. J. Parola
“Using Hydrogen Bonding Specific Interactions to Detect Water in Aprotic Solvents at Concentrations Below 50 ppm”
Sens. Actuat. B, 2006, 114, 978-983

L. Giestas, F. Folgosa, J. C. Lima, A. J. Parola, F. Pina
“Bio-Inspired Multistate Networks Responsive to Light, pH and Thermal Inputs. An Example of a Multistate System Operating Through Different Algorithms.”
Eur. J. Org. Chem., 2005, 4187-4200

F. Galindo, J. C. Lima, S. V. Luis, M. J. Melo, A. J. Parola, F. Pina
“Water/humidity, and ammonia sensor, based on a polymer hydrogel matrix containing a fluorescent flavylium compound.”
J. Mater. Chem., 2005, 15, 2840-2847

F. Galindo, J. C. Lima, S. V. Luis, A. J. Parola, F. Pina
“Write-Read-Erase Molecular Switching System Trapped in a Polymer Hydrogel Matrix.”
Adv. Funct. Mat., 2005, 15, 541-545

F. Pina, J. C. Lima, A. J. Parola, C. A. M. Afonso
“Thermal and Photochemical Properties of 4’,7-dihydroxyflavylium in Water-Ionic Liquids Biphasic Systems. A Novel Approach to a Write-Read-Erase Molecular Switching System.”
Angew. Chem. Int. Ed., 2004, 43, 1525-1527

M. C. Moncada, A. J. Parola, C. Lodeiro, F. Pina, M. Maestri, V. Balzani
“Multistate/Multifunctional Behaviour of 4’-hydroxy-6-nitroflavylium. A Write-lock/Read/Unlock/ Enable-erase/Erase Cycle Driven by Light and pH Stimulation”
Chem. Eur. J., 2004, 10, 1519-1526

M. Vicente, R. Bastida, C. Lodeiro, A. Macías, A. J. Parola, L. Valencia, S. E. Spey
“Metal Complexes with a New N4O3 Scorpionand Macrocyclic Ligand. Synthesis, Characterization, Crystal Structures and Fluorescence Studies”
Inorg. Chem., 2003, 42, 6768-6779

M. T. Albelda, P. Díaz, E. Garcia-España, J. C. Lima, C. Lodeiro, J. Seixas de Melo, A. J. Parola, F. Pina, C. Soriano
“Switching from intramolecular energy transfer to intramolecular electron transfer by the action of pH and Zn2+ co-ordination”
Chem. Phys. Lett., 2002, 353, 63-68

C. Lodeiro, F. Pina, A. J. Parola, A. Bencini, A. Bianchi, C. Bazzicalupi, C. Giorgi, A. Masotti, B. Valtancoli, J. Seixas de Melo
“Exploring the Photocatalytic Properties and the Long-Lifetime Chemosensor Ability of Cl2[Ru(Bpy)2L] (L = 2,5,8,11,14-Pentaaza[15])-2,2'-bipyridilophane)”
Inorg. Chem., 2001, 40, 6813-6819

A. Bencini, A. Bianchi, C. Lodeiro, A. Masotti, A. J. Parola, F. Pina, J. Seixas de Melo, B. Valtancoli
“A Novel Fluorescent Chemosensor Exhibiting Exciplex Emission. An Example of an Elementary Molecular Machine Driven by pH and by Light”
Chem. Commun., 2000, 1639-1640

F. Pina, A. J. Parola
“Photochemistry of Supramolecular Species Involving Anionic Coordination Compounds and Polyammonium Macrocyclic Receptors”
Coord. Chem. Rev., 1999, 185-186, 149-165

F. Pina, M. J. Melo, A. J. Parola, M. Maestri, V. Balzani
“pH-Controlled Photochromism of Hydroxyflavylium Ions”
Chem. Eur. J., 1998, 4, 2001-2007

A. J. Parola, F. Pina, M. F. Manfrin, L. Moggi
“Supramolecular Interactions Between Co(CN)5(SO3)4– and Polyammonium Macrocyclic Receptors”
J. Chem. Soc., Dalton Trans., 1998, 1005-1010

F. Pina, A. J. Parola, A. Saint-Maurice, M. F. Manfrin, L. Moggi, T. Indelli, F. Scandola
“Electron Transfer Between Fe(CN)63– and Iodide Promoted by Supercomplexation with [32]ane-N8H88+“
J. Chem. Soc., Dalton Trans., 1997, 2327-2330

A. J. Parola, F. Pina, E. Ferreira, M. Maestri, V. Balzani
“Photoinduced Electron and Energy Transfer Processes of Biacetyl Imprisoned in a Hemicarcerand”
J. Am. Chem. Soc., 1996, 118, 11610-11616

M. A. Rampi, M. T. Indelli, F. Scandola, F. Pina, A. J. Parola
“Photophysics of Supercomplexes. Adduct between Ru(bpy)(CN)42– and the [32]ane- N8H88+ Polyaza Macrocycle”
Inorg. Chem., 1996, 35, 3355-3361

A. J. Parola, F. Pina, E. Ferreira, M. Maestri, N. Armaroli, R. Ballardini, V. Balzani
“Supramolecular Photochemistry and Photophysics. Biacetyl Imprisoned in a Hemicarcerand”
J. Phys. Chem., 1995, 99, 12701-12703

A. J. Parola, F. Pina, M. Maestri, N. Armaroli, V. Balzani
“Supramolecular Photochemistry and Photophysics. 9-Cyanoanthracene Imprisoned in a Hemicarcerand”
New J. Chem. 1994, 18, 659-661

A. J. Parola, F. Pina
“Photochemistry of the Adduct between [Co(CN)5H2O]2– and the Polyammonium Macrocyclic Receptor [32]ane-N8. Evidence for the Supramolecular Structure”
J. Photochem. Photobiol., A: Chem., 1992, 66, 337-343

N. Jordão, R. Gavara, A. J. Parola, “Flavylium-Supported Poly(N-isopropylacrylamide): A Class of Multistimuli Responsive Polymer”, Macromolecules,2013, 46(22), 9055-9063, DOI: 10.1021/ma401497q

F. Pina, M. J. Melo, C. A. T. Laia, A. J. Parola, J. C. Lima, “Chemistry and Applications of Flavylium Compounds: a Handful of Colours”, Chem. Soc. Rev., 2012, 41(2), 869-908, DOI: 10.1039/c1cs15126f

R. Gomes, A. J. Parola, F. Bastkowski, J. Polkowska, F.-G. Klärner, “Host-guest interactions between molecular clips and multistate systems based on flavylium salts”,J. Am. Chem. Soc., 2009, 131, 8922–8938, DOI: 10.1021/ja9019098

F. Pina, J. C. Lima, A. J. Parola, C. A. M. Afonso, “Thermal and Photochemical Properties of 4’,7-dihydroxyflavylium in Water-Ionic Liquids Biphasic Systems. A Novel Approach to a Write-Read-Erase Molecular Switching System.”, Angew. Chem. Int. Ed., 2004, 43, 1525-1527, DOI: 10.1002/anie.200353131

A. J. Parola, F. Pina, E. Ferreira, M. Maestri, V. Balzani, “Photoinduced Electron and Energy Transfer Processes of Biacetyl Imprisoned in a Hemicarcerand”, J. Am. Chem. Soc., 1996, 118, 11610-11616, DOI: 10.1021/ja962450q

Websites

http://www.researcherid.com/rid/F-4048-2010

http://sites.fct.unl.pt/fotoquimica/people/jorge-parola