Supramolecular Chemistry Team (CS)

Research area:

Our researches focus on the development and use of cage compounds (cyclodextrins, crown ethers) for the complexation and detection of organic and inorganic compounds.

These researches require, as a first step, the synthesis and modification of host molecules, in order to optimize their scavenging, solubilising or spectral sensitivity properties.
To fit into a sustainable development approach, these syntheses are performed using non conventional methods (microwave, ultrasound) in aqueous solution, even in the absence of solvent.
Moreover, the applications associated with cage compounds are largely determined by the stability of the complexes formed with guests. Understanding the mechanisms involved in the recognition is essential for the « design » of new compounds and therefore constitutes a major focus of our academic research.
In this perspective, we develop innovative characterization methods (optical spectroscopy, NMR, headspace, isothermal titration calorimetry). Simulation of complexes by molecular mechanics and quantum mechanics are also investigated.

Application of the supramolecular complexes is then conducted in three main areas:

Development of organic and hybrid materials for the trapping and detection of pollutants

New organic and/or hybrid materials are obtained by combining fluorescent cage molecules and silica matrices in order to achieve the trapping and detection of gaseous pollutants (VOCs) or metallic cations such as Fe(III). The development of these structures involves among others sol-gel processes, including the development of organized silica.

Encapsulation of compounds of interest (flavours, essential oils, active compounds)

Encapsulation permits to trap liquids or solids in a dedicated envelope. Cyclodextrins can protect active ingredients against both physical and chemical degradation or allow the controlled or sustained release of active compounds. Our work involves the characterization of the inclusion complexes in solution or solid phase and the investigation of the effect of encapsulation on the physicochemical and/or biological properties of the guest.

Development of remediation methods

Among remediation methods currently available, one of the main limitations remains the low solubility of hydrophobic organic compounds in water. Our researches consist to develop innovative methods adapted to hydrophobic organic compounds (VOCs, POP…) based on the complexation and solubilisation properties of cyclodextrins. Association with advanced oxidation processes (Fenton, photocatalysis) is also studied.

 

Supramolecular chemistry team members :


CAZIER Francine

MCF-HDR

DANJOU Pierre-edouard

MCF

DELATTRE François

MCF-HDR

FOURMENTIN Sophie

Pr

LANDY David

Pr

MALLARD Isabelle

MCF

RUELLAN Steven

IE

 

Collaborations :

Nationals :

  • Unité de Catalyse et Chimie du solide (UCCS Artois), UMR CNRS 8181, Université d’Artois, Lens.
  • Unité des Matériaux et Transformations (UMET), UMR 8207, Université de Lille 1, Villeneuve d’Ascq.
  • Groupe de Recherche Interdisciplinaire Innovation et Optimisation Thérapeutique (EA 4481), Lille 2.
  • Institut Galien Paris-Sud (UMR CNRS 8612), Université Paris-Sud.
  • Chimie, Structures, Propriétés de Biomatériaux et d’Agents Thérapeutiques, UMR CNRS 7244, Université Paris 13.
  • Institut de Chimie de Clermont-Ferrand (ICCF), UMR 6296, Clermont-Ferrand.

Internationals :

  • Organische Makromolekulare Chemie, Universitaet des Saarlandes, Allemagne.
  • Section of Chemistry, Department of Biotechnology, Chemistry and Environmental Engineering, Aalborg University, Danemark
  • Dipartimento di Chimica, Materiali ed Ingegneria Chimica « G. Natta, Politecnico di Milano, Italie
  • Department of Chemical and Food Engineering, Université Vasile Alecsandri, Roumanie.
  • Department of Applied Chemistry, Organic and Natural Compounds Engineering Polytechnic, Université de Timisoara, Roumanie
  • Bioactive Molecules Research Group, Department of Chemistry and Biochemistry, Faculty of Sciences-2, Lebanese University, Liban
  • Laboratoire de Photochimie et d’Analyse, Université Cheikh Anta Diop de Dakar, Sénégal.

PhD in progress :

 

First Name    Name

Period

Title

Joyce Azzi

 

2014-2017

Improved nutritional and organoleptic qualities of foods by encapsulation of active compounds (flavors, vitamins, antioxidants, unsaturated fatty acids … )

Clémence Moitessier 2015-2018 Selective analysis of biogenic amines on fluorescent nanomaterials incorporating Quantum Dot-Light Emitting Diode (QD-LED)
Khemesse Kital 2015-2018 Characterization of biogenic ortho-phthalaldehyde-amine complexes by Nuclear Magnetic Resonance and molecular fluorescence
Eliane Saliba 2015-2018 Pentacyclic triterpenes of olive oil: chemical stability, interactions with plasma proteins and identification of pathways of biotransformation in animals.
Corentin Musa 2016-2019 Elaboration by sonochemistry and characterization of biosourced composite materials based on mucilaginous bioadhesives and Linen fibers
Tarek Moufawad 2016-2019 Development of new solvents for VOC absorption

 

Research projects :

  • Project PEPPAZU « Perception and evaluation of pesticides in air near urban area » (2014-2017)- Funded by Nord-Pas de Calais region
  • ADEME CORTEA DESCOV (2014-2016)
  • Ultralin: « Application development of sonochemical processes for the upgrading of linen fibers »

 Recent publications :

  • J. Azzi, P-E. Danjou, D. Landy, S. Ruellan, L. Auezova, H. Greige-Gerges, S. Fourmentin : Effect of cyclodextrins complexation on solubility and photostability of nerolidol as pure compound and as main constituent of Cabreuva essential oil, Beilstein J. Org. Chem., 13, 835–844, 2017. DOI: 10.3762/bjoc.13.84.
  • G. Vermet, S. Degoutin, F. Chai, M. Maton, C. Flores, C. Neut, P-E. Danjou, B. Martel, N. Blanchemain : Cyclodextrin modified PLLA parietal reinforcement implant with prolonged antibacterial activity, Acta Biomater., 53, 222-232, 2017. DOI:10.1016/j.actbio.2017.02.017.
  • L. Cisse, A. Djande, M. Capo-Chichi, F. Delattre, A. Saba, J.-C. Brochon, S. Sanouski, A. Tine, J.-J. Aaron: Fluorescence quenching of two coumarin-3-carboxylic acids by trivalent lanthanide ions, J. Fluoresc., 27(2), 619-628, 2017. DOI:10.1007/s10895-016-1990-1.
  • M. Kfoury, D. Landy, S. Ruellan, L. Auezova, H. Greige-Gerges, S. Fourmentin : Nootkatone encapsulation by cyclodextrins: effect on water solubility and photostability, Food Chem., 236, 41-48, 2017. DOI: 10.1016/j.foodchem.2016.12.086.
  • M. Kfoury, J.D. Pipkin, V. Antle, S. Fourmentin : Captisol®: an efficient carrier and solubilizing agent for essential oils and their components, Flavour Frag. J., 32, 340–346, 2017. DOI:10.1002/ffj.3395.
  • M. Monteil, M. Lecouvey, D. Landy, S. Ruellan, I. Mallard : Cyclodextrins: A promising drug delivery vehicle for bisphosphonate, Carbohydr. Polym., 156, 285-293, 2017. DOI: 10.1016/j.carbpol.2016.09.030.
  • S. Fourmentin, D. Landy : Développement de solvants verts pour la remédiation des composés organiques volatils, L’actualité chimique, 420, 2-27, 2017.
  • C.H. Nguyêna, J-L .Putaux, G. Santoni, S. Fourmentin, J-B. Coty, L. Choisnard, A. Gèze, D. Wouessidjewe, G. Barratt, S. Lesieur, F-X. Legrand : New nanoparticles obtained by co-assembly of amphiphilic cyclodextrins and nonlamellar single-chain lipids: Preparation and characterization. Int. J. Pharm., DOI:10.1016/j.ijpharm.2017.07.007.
  • L. Moura, T. Moufawad, M. Ferreira, H. Bricout, S. Tilloy, E. Monflier, M.F. Costa Gomes, D. Landy, S. Fourmentin : Deep eutectic solvents as promising media for the absorption of volatile organic compounds, Environ. Chem. Lett., DOI:10.1007/s10311-017-0654-y.
  • M.A. Moussawi, N. Leclerc-Laronze, S. Floquet, P.A. Abramov, M.N. Sokolov, S. Cordier, A. Ponchel, E. Monflier, H. Bricout, D. Landy, M. Haouas, J. Marrot, E. Cadot: Polyoxometalate, Cationic Cluster and g-cyclodextrin. From Primary Interactions to Supramolecular Hybrid Materials, J Am Chem Soc., 2017. DOI: 10.1021/jacs.7b07317.
  • N. Morin-Crini, P. Winterton, S. Fourmentin, L.D. Wilson, E. Fenyvesi, G. Crini : Water-insoluble b-cyclodextrin–epichlorohydrin polymers for removal of pollutants from aqueous solutions by sorption processes using batch studies: A review of inclusion mechanisms, Prog. Polym. Sci., DOI:10.1016/j.progpolymsci.2017.07.004.
  • M. Kfoury, A. Lounès-Hadj Sahraoui, N. Bourdon, F. Laruelle, J. Fontaine, L. Auezova, H. Greige-Gerges, S. Fourmentin : Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins, Food Chem., 196, 518-525, 2016. DOI: 10.1016/j.foodchem.2015.09.078.
  • I. Delsarte, P.-E. Danjou, E. Veignie, C. Rafin : Synthesis of modified potato starches for aqueous solubilization of benzo[a]pyrene, Carbohydr. Polym.,144, 83-88, 2016. doi:10.1016/j.carbpol.2016.01.071.
  • A. Lannoy, N. Kania, R. Bleta, S. Fourmentin, C. Machut-Binkowski, E. Monflier, A. Ponchel : Photocatalysis of volatile organic compounds in water: toward a deeper understanding of the role of cyclodextrins in the photodegradation of toluene over titanium dioxide, J. Colloid Interface Sci., 461, 317-325, 2016. DOI:10.1016/j.jcis.2015.09.022.
  • A. Diop, Y.M. Diop, D.D. Thiaré, F. Cazier, S. Sarr, A. Kasprowiak, D. Landy, F. Delattre : Monitoring survey of the use patterns and pesticide residues on vegetables in the Niayes zone, Senegal, Chemosphere, 144, 1715-1721, 2016. doi: 10.1016/j.chemosphere.2015.10.058.
  • H. Chaker, L. Chérif-Aouali, S. Khaoulani, A. Bengueddach, S. Fourmentin : Photocatalytic degradation of methyl orange and real wastewater by silver doped mesoporous TiO2 catalysts, J. Photochem. Photobiol. A. 318, 142-149, 2016. DOI:10.1016/j.jphotochem.2015.11.025.
  • J. Junthip, N. Tabary, F. Chai, L. Leclercq, M. Maton, F. Cazaux, C. Neut, L. Paccou, Y. Guinet, J.-N. Staelens, M. Bria, D. Landy, A. Hédoux, N. Blanchemain, B. Martel : Layer-by-layer coating of textile with two oppositely charged cyclodextrin polyelectrolytes for extended drug delivery, J. Biomed. Mater. Res. A, 104 (6), 1408-1424, 2016. DOI: 10.1002/jbm.a.35674.
  • M. Kfoury, D. Landy, S. Ruellan, L. Auezova, H. Greige-Gerges, S. Fourmentin : Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol, Beilstein J. Org. Chem., 12, 29-42, 2016. DOI:10.3762/bjoc.12.5.
  • M. Kfoury, L. Auezova, H. Greige-Gerges, K.L. Larsen, S. Fourmentin : Release studies of trans-anethole from β-cyclodextrin solid inclusion complexes by Multiple Headspace Extraction, Carbohydr. Polym., 151, 1245-1250, 2016. DOI: 10.1016/j.carbpol.2016.06.079.
  • M. Kfoury, L. Auezova, H. Greige-Gerges, S. Fourmentin : Development of a Total Organic Carbon method for the quantitative determination of solubility enhancement by cyclodextrins: Application to essential oils, Anal. Chim. Acta, 918, 21-25, 2016. DOI:10.1016/j.aca.2016.03.013.
  • M. Kfoury, M. Borgie, A. Verdin, F. Ledoux, D. Courcot, L. Auezova, S. Fourmentin : Essential oils components decrease pulmonary and hepatic cells inflammation induced by air pollution particulate matter, Environ. Chem. Lett., 14, 345-361, 2016. DOI: 10.1007/s10311-016-0572-4.
  • N. Mofaddel, S. Fourmentin, F. Guillen, D. Landy, G. Gouhier : Ionic Liquids and Cyclodextrins Inclusion Complexes. Limitation of Affinity Capillary Electrophoresis Technique, Anal. Bioanal. Chem., 408, 8211-8220, 2016. DOI 10.1007/s00216-016-9931-z.
  • S. Khaoulani, M. Kassem, S. Fourmentin, E. Bychkov : The AgI-HgS-As2S3 glassy system: Macroscopic properties and Raman scattering studies, J. Alloys Compd., 685, 752-760, 2016. DOI:10.1016/j.jallcom.2016.06.197.