Collaborations

Eco-friendly photochemical oxidation of sulfides


  • In collaboration with: Prof. Sergio Bonesi - University of Buenos Aires, Argentina

The partnership with the University of Buenos Aires focuses on the photochemical oxidation under mild conditions of sulfur-containing derivatives (sulfides). This process is of great environmental importance due to the presence of sulfur containing oil compounds that during their combustion are responsible of increasing the atmospheric pollution.

The aim of the cooperation is transforming the sulfides in water-soluble (thus easily removable) derivatives by a photochemical oxidation. When the oxidation is purposely controlled, organic sulfides could be converted into sulfoxides (compounds of synthetic interest) under environmental friendly conditions.


Selected publications

  1. Bonesi, S. M.; Fagnoni, M.; Albini, A. "Photosensitized electron transfer oxidation of sulfides: structure and medium effect" J. Sulfur Chem. 2008, 29, 367-376. DOI: 10.1080/17415990802105762
  2. Bonesi, S. M.; Fagnoni, M.; Albini, A. "Photosensitized Electron Transfer Oxidation of Sulfides: A Steady-State Study" Eur. J. Org. Chem. 2008, 2008, 2612-2620. DOI: 10.1002/ejoc.200800048
  3. Bonesi, S. M.; Carbonell, E.; Garcia, H.; Fagnoni, M.; Albini, A. "Photocatalytic oxidation of aliphatic and aromatic sulfides in the presence of silica adsorbed or zeolite-encapsulated 2,4,6-triphenyl(thia)pyrylium" Appl. Catal. B-Environ. 2008, 79, 368-375. DOI: 10.1016/j.apcatb.2007.10.037

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Mechanistic study of photochemical reactions


  • In collaboration with: Prof. Sandra Monti - ISOF-CNR, Bologna, Italy

Our lab has been working with the group in Bologna since many years, exploiting their long experience with the laser flash photolysis technique, as well as with other advanced lifetime measurements of various chemical species (e.g. singlet oxygen). Thanks to the availability of these sophisticated laser instruments, the detection of extremely fast transient species is possible, allowing for a deeper comprehension of the mechanism of the reactions under investigation.


Selected publications

  1. Protti, S.; Fagnoni, M.; Monti, S.; Réhault, J.; Poizat, O.; Albini, A. "Activation of aliphatic C-H bonds by tetracyanobenzene photosensitization. A time-resolved and steady-state investigation." RSC Adv. 2012, 2, 1897-1904. DOI: 10.1039/C2RA01054B
  2. Fasani, E.; Manet, I.; Capobianco, M. L.; Monti, S.; Pretali, L.; Albini, A. "Fluoroquinolones as potential photochemotherapeutic agents: covalent addition to guanosine monophosphate" Org. Biomol. Chem. 2010, 8, 3621-3623. DOI: 10.1039/c0ob00056f
  3. Manet, I.; Monti, S.; Grabner, G.; Protti, S.; Dondi, D.; Dichiarante, V.; Fagnoni, M.; Albini, A. "Revealing Phenylium, Phenonium, Vinylenephenonium, and Benzenium Ions in Solution" Chem. Eur. J. 2008, 14, 1029-1039. DOI: 10.1002/chem.200701043
  4. Bonesi, S. M.; Fagnoni, M.; Monti, S.; Albini, A. "Reaction of singlet oxygen with some benzylic sulfides." Tetrahedron 2006, 62, 10716-10723. DOI: 10.1016/j.tet.2006.07.110
  5. Manet, I.; Monti, S.; Fagnoni, M.; Protti, S.; Albini, A. "Aryl Cation and Carbene Intermediates in the Photodehalogenation of Chlorophenols" Chem. Eur. J. 2005, 11, 140-151. DOI: 10.1002/chem.200400681

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Photoreactivity of flavonoids


  • In collaboration with: Dr. Alberto Mezzetti - LASIR, USTL-University of Lille, France

Flavonoids are an important photochemical target due to their vast technological applications, e.g. as laser sources or as biological sensors. This study makes use of various spectroscopic techniques, such as UV-visible, infrared and Raman spectroscopy, both time-resolved and under steady-state conditions.


Selected publications

  1. Protti, S.; Mezzetti, A. "Any colour you like. Excited state and ground state proton transfer in flavonols and applications" in Specialistic Periodical reports: Photochemistry; Albini, A. Ed. 2012, 40, pp. 295-322, Royal Society of Chemistry.
  2. Mezzetti, A.; Protti, S.; Lapouge, C.; Cornard, J.-P. "Protic Equilibria as the key factor of quercetin emission in solution. Relevance to biochemical and analytical studies" Phys. Chem. Chem. Phys. 2011, 13, 6858-6864. DOI: 10.1039/C0CP00714E
  3. Protti, S.; Raulin, K.; Cristini, O.; Turrell, S.; Mezzetti, A. "Wavelength shifting system based on flavonols and their metal complexes encapsulated in porous SiO2 matrices" J. Mol. Struct. 2011, 993, 485-490. DOI: 10.1016/j.molstruc.2011.02.010
  4. Protti, S.; Mezzetti, A.; Cornard, J.-P.; Lapouge, C.; Fagnoni, M. "Hydrogen bonding properties of DMSO in ground-state formation and optical spectra of 3-hydroxyflavone anion" Chem. Phys. Lett. 2008, 467, 88-93. DOI: 10.1016/j.cplett.2008.11.005
  5. Protti, S.; Mezzetti, A.; Lapouge, C.; Cornard, J.-P. "Photochemistry of metal complexes of 3-hydroxyflavone: towards a better understanding of the influence of solar light on the metal-soil organic matter interactions" Photochem. Photobiol. Sci. 2008, 7, 109-119. DOI: 10.1039/B709682H

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Synthesis of ionic liquids as electrolites for lithium batteries


  • In collaboration with: Prof. Piercarlo Mustarelli - Department of Chemistry, University of Pavia

The study focuses on the synthesis of ionic liquids and on their application as electrolytes in membranes applied to rechargeable lithium batteries. In our laboratory, the project focuses on the design, preparation and purification of new ionic liquids having the physical and chemical properties most suitable for this purpose.


Selected publications

  1. Quinzeni, I.; Ferrari, S.; Quartarone, E.; Tomasi, C.; Fagnoni, M.; Mustarelli, P. "Li-doped mixtures of alkoxy-N-methylpyrrolidinium bis(trifluoromethanesulfonyl)-imide and organic carbonates as safe liquid electrolytes for lithium batteries" J. Power Sources 2013, 237, 204-209. DOI: 10.1016/j.jpowsour.2013.03.036
  2. Ferrari, S.; Quartarone, E.; Tomasi, C.; Ravelli, D.; Protti, S.; Fagnoni, M.; Mustarelli, P. "Alkoxy substituted imidazolium-based ionic liquids as electrolytes for lithium batteries" J. Power Sources 2013, 235, 142-147. DOI: 10.1016/j.jpowsour.2013.01.149
  3. Abitelli, E.; Ferrari, S.; Quartarone, E.; Mustarelli, P.; Magistris, A.; Fagnoni, M.; Albini, A.; Gerbaldi, C. "Polyethylene oxide electrolyte membranes with pyrrolidinium-based ionic liquids" Electrochim. Acta 2010, 55, 5478-5484. DOI: 10.1016/j.electacta.2010.04.099
  4. Lavall, R. L.; Ferrari, S.; Tomasi, C.; Marzantowicz, M.; Quartarone, E.; Magistris, A.; Mustarelli, P.; Lazzaroni, S.; Fagnoni, M. "Novel polymer electrolytes based on thermoplastic polyurethane and ionic liquid/lithium bis(trifluoromethanesulfonyl)imide/propylene carbonate salt system" J. Power Sources 2010, 195, 5761-5767. DOI: 10.1016/j.jpowsour.2010.03.085
  5. Ferrari, S.; Quartarone, E.; Mustarelli, P.; Magistris, A.; Fagnoni, M.; Protti, S.; Gerbaldi, C.; Spinella. A. "Lithium ion conducting PVdF-HFP composite gel electrolytes based on N-methoxyethyl-N-methylpyrrolidinium bis(trifluoromethanesulfonyl)-imide ionic liquid" J. Power Sources 2010, 195, 559-566. DOI: 10.1016/j.jpowsour.2009.08.015

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Functionalization of carbon nanotubes and their applications


  • In collaboration with: Prof. Piercarlo Mustarelli, Prof. Antonella Profumo - Department of Chemistry, University of Pavia - and Prof. Livia Visai - Department of Biochemistry, University of Pavia

Carbon nanotubes are potentially useful materials for nano-objects to be used as biosensors, drug delivery carriers as well as in the field of energy. One of the major drawbacks limiting the application of carbon nanotubes is their low solubility in aqueous or organic solvents. The collaboration aims at finding new methods for the functionalization of these materials in order to increase their solubility. The nanotubes thus obtained are then characterized (for example with TGA, TEM or SEM) and used in photoelectrochemical studies or as drug carriers, after conjugation with biologically active molecules.


Selected publications

  1. Ravelli, D.; Montanaro, S.; Tomasi, C.; Galinetto, P.; Quartarone, E.; Merli, D.; Mustarelli, P.; Fagnoni, M. "One-Step Decatungstate-Photomediated PEGylation of Single-Walled Carbon Nanotubess" ChemPlusChem 2012, 77, 210-216. DOI: 10.1002/cplu.201100040
  2. Merli, D.; Ugonino, M.; Profumo, A.; Fagnoni, M.; Quartarone, E.; Mustarelli, P.; Visai, L.; Grandi, M. S.; Galinetto, P.; Canton, P. "Increasing the antibacterial effect of lysozyme by immobilization on multi-walled carbon nanotubes" J. Nanosci. Nanotechno. 2011, 11, 3100-3106. DOI: 10.1166/jnn.2011.3758
  3. Fagnoni, M.; Profumo, A.; Merli, D.; Dondi, D.; Mustarelli, P.; Quartarone, E. "Water-miscible liquid multiwalled carbon nanotubes" Adv. Mater. 2009, 21, 1761- 1765. DOI: 10.1002/adma.200801994
  4. Merli. D.; Profumo, A.; Dondi, D.; Albini, A. "Photoelectrochemical Studies of Gold Electrodes Chemically Modified with Single-Walled Carbon Nanotubes" ChemPhysChem 2009, 10, 1090-1096. DOI: 10.1002/cphc.200800684

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Synthesis of new organic superconductors


  • In collaboration with: Dr. Lorenzo Malavasi - Department of Chemistry, University of Pavia

Obtaining easily synthesized systems able to show superconducting properties at relatively high temperatures (18 K) is a primary goal of the research in this field. The collaboration (started in 2011) with the group of Dr. Malavasi aims at developing innovative organic superconductors based on the family of phenacenes (polycondensed aromatic compounds, such as phenanthrene or picene) intercalated with alkali or alkaline-earth metals. Our aim is the optimization of a general, unexpensive photochemical synthetic procedure for obtaining (substituted) phenacenes.


Selected publications

  1. Joseph, B.; Boeri, L.; Malavasi, L.; Capitani, F.; Artioli, G. A.; Protti, S.; Fagnoni, M.; Albini, A.; Marini, C.; Baldassarre, L.; Perucchi, A.; Lupi, S.; Postorino P.; Dore, P. "Vibrational spectrum of solid picene (C22H14)" J. Phys.: Condens. Matter 2012, 24, 252203. DOI: 10.1088/0953-8984/24/25/252203

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Predicting the properties of Polyoxometalates by DFT


  • In collaboration with: Prof. Alessando Bagno - University of Padova, Italy

The collaboration concerns with the application of computational methods to the prediction of the properties of polyoxometalates, e.g. the decatungstate anion. In particular, this project aims at simulating the UV-VIS spectra of this family of compounds through the application of the TD-DFT (Time Dependent - Density Functional Theory) method.


Selected publications

  1. Ravelli, D.; Dondi, D.; Fagnoni, M.; Albini, A.; Bagno, A. "Electronic and EPR spectra of the species involved in [W10O32]4− photocatalysis. A relativistic DFT investigation" Phys. Chem. Chem. Phys. 2013, 15, 2890-2896. DOI: 10.1039/C2CP43950F
  2. Ravelli, D.; Dondi, D.; Fagnoni, M.; Albini, A.; Bagno, A. "Predicting the UV spectrum of polyoxometalates by TD-DFT" J. Comput. Chem. 2011, 32, 2983-2987. DOI: 10.1002/jcc.21879

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Photochemical radical processes


  • In collaboration with: Prof. Ilhyong Ryu - Osaka Prefecture Univeristy, Osaka, Japan

The collaboration involves the discovery and development of innovative radical syntheses. In particular, it aims at devising multi-component processes, that take advantage of the photochemical activation in combination with the use of carbon monoxide (CO) as a radical trap.


Selected publications

  1. Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. "Efficient C-H/C-N and C-H/C-CO-N Conversion via Decatungstate-Photoinduced Alkylation of Diisopropyl Azodicarboxylate" Org. Lett. 2013, 15, 2554-2557. DOI: 10.1021/ol401061v
  2. Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Albini, A. "Atom-Economical Synthesis of Unsymmetrical Ketones through Photocatalyzed C-H Activation of Alkanes and Coupling with CO and Electrophilic Alkenes" Angew. Chem. Int. Ed. 2011, 50, 1869-1872. DOI: 10.1002/anie.201004854

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Photochemical synthesis under ecosustainable conditions


  • In collaboration with: Dr. Alessandro Palmieri, - University of Camerino, Italy - Prof. Luigi Vaccaro and Dr. Daniela Lanari - University of Perugia, Italy
    Financial support from: MIUR - FIRB 2008 (RBFR08J078Q)

The project is based on the development of procedures for the photoinduced formation of C-C and C-heteroatom bonds under environmental friendly conditions. A further development is the optimization of continuous flow multi-step processes, able to combine photochemical/photocatalyzed reactions (Pavia) and processes carried out under heterogeneous catalysis (Camerino - Perugia).


Selected publications

  1. Protti, S.; Palmieri, A.; Petrini, M.; Fagnoni, M.; Ballini, R.; Albini, A. "A Photochemical Route to Benzo[a]carbazoles via Domino Elimination/Electrocyclization of 2-Aryl-3-(1-tosylalkyl)indoles" Adv. Synth. Catal. 2013, 355, 643-646. DOI: 10.1002/adsc.201201051

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PhotoAcid Generators (PAGs) synthesis and applications in photolithography


  • In collaboration with: Dr. Gioia Della Giustina, Prof. Giovanna Brusatin - INSTM Padova, Italy - and Dr. Luca Mezi - ENEA Roma, Italy
    Financial support from: Fondazione Cariplo (2012-0186)

The project is based on the preparation of neutral compounds, able to release strong acid molecules when photochemically activated (PhotoAcid Generators - PAGs). The synthesized molecules will be exploited in the laboratories of Padova and Roma in photolithography processes promoted by UV and soft-X radiations.


Selected publications

  1. Terpolilli, M.; Merli, D.; Protti, S.; Dichiarante, V.; Fagnoni, M.; Albini, A. "Cationic and Radical Intermediates in the Acid Photorelease from Aryl Sulfonates and Phosphates" Photoch. Photobio. Sci. 2011, 10, 123-127. DOI: 10.1039/C0PP00284D

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Other collaborations


Other collaborations with national and international research laboratories involve the groups of Prof. M. Oelgemöller (James Cook University, Townsville, Australia), Prof. E. Lacôte (ICSN-CNRS, Gif-sûr-Yvette, France) and Prof. W. Leibl (Laboratory of photocatalysis and biohydrogen research (LPB) - CEA, Saclay, France).


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