Supramolecular Chemistry Team (CS)

Research activity

The supramolecular chemistry team’s research activities are in the field of sustainable chemistry, at the interface of two disciplines: organic synthesis and supramolecular chemistry. They contribute to the development of more environmentally friendly chemical processes by developing unconventional synthesis methods (ultrasound, microwave) as well as methods for detecting or remedying pollutants and encapsulating bioactive compounds.

Moreover, since the applications associated with cage molecules are largely conditioned by the stability of the complexes formed with the substrates, understanding the mechanisms involved during recognition is essential for the “design” of new compounds and is therefore a strong focus of our academic research. In this framework, we develop innovative characterization methods (optical and NMR spectroscopy, headspace, isothermal titration microcalorimetry), which we confront with the simulation of complexes by molecular mechanics and quantum mechanics.

The application of the supramolecular buildings thus formed is then carried out along two main axes:

Remediation and detection of organic and inorganic pollutants

Among the remediation processes currently available, one of the main limitations remains the low solubility of hydrophobic organic compounds in water. Our research work consists in developing innovative methods adapted to hydrophobic organic compounds (VOC, POP…) and based on the complexing and solubilization properties of cyclodextrins or biosourced solvents.

New organic and/or hybrid materials are obtained by combining fluorescent cage molecules and silicic matrices and, with the aim of trapping and detecting gaseous pollutants (VOC) or metallic cations such as Fe(III). The development of these structures requires, among other things, sol-gel processes, particularly for the production of organized silica.

Encapsulation of compounds of interest (aromas, essential oils, active ingredients)

Encapsulation is a technique to trap liquids or solids in an envelope. Cyclodextrins can thus protect active ingredients against physical degradation, chemical degradation or to allow controlled or prolonged release of active ingredients. Our work consists in characterizing the complexes thus formed in solution (UV-visible, headspace, ITC, NMR) or in solid phase (DSC, IR) and in studying the effect of encapsulation on the physicochemical and/or biological properties of the guest.

Our sonochemical synthesis expertise has been put to good use in an emerging area:

Valorisation of biomass

This research theme aims to develop, from products derived from Linen (fibre, mucilage), a base of biosourced compounds (resins, adhesives, binders) for the formulation of new materials. It is part of a partnership with the Lin regional sector. With a view to possible industrial upgrading, semi-pilot sonochemical reactors are being developed for the production of high-quality fibres and the functionalization of biomass.

Team members

Scientific 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.
  • Laboratoire de chimie, ENS Lyon.
  • Chimie, Structures, Propriétés de Biomatériaux et d’Agents Thérapeutiques, UMR CNRS 7244, Université Paris 13.
  • Institut de Chimie Séparative de Marcoule (ICSM), UMR CEA/CNRS/UM/ENSCM 5237, Equipe Systèmes HYbrides pour la Séparation (LHYS).
  • Institut des Sciences de l’Évolution Montpellier (ISEM), équipe Evolution vecteurs adaptation et symbiose, Université Montpellier 2.

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.

Current thesis

Name

Period

Title

Tracy El Achkar

2017-2020

Encapsulation of bioactive compounds: effect on their physico-chemical and biological properties

Nancy Haddad

2017-2020

Synthesis of novel complexing entities based on calix[4]pyrrole for the decontamination of natural radionuclides in aquatic environments

Lamia Nakhle

2018-2021

Encapsulation of bioactive principles by modified cyclodextrins in deep eutectic mixtures

Bastien Watbled

2019-2022

Elaboration and characterization of flax-based biocomposites with improved fire behaviour

Sarah El Masri

2019-2022

Vectorization of bioactive compounds in deep eutectic solvents: study of their solubility and bioavailability

Research agreement

  • 2020-2024 : ” Dunkerque, l’Energie Créative “,
  • project, winning project of the Territoires d’innovation (TI) action under the PIA.
  • 2020-2023 : H2020-MSCA-RISE-2019 n°873005: Waste Oils RecycLe and Development (WORLD). 5 academic partners (France, Italy, Spain, Algeria) and 2 industrial partners (Italy, Spain). Project led by the Polytechnic Institute of Milan, Pr Andrea Mele.
  • 2020-2022 : PHC Utique 44209NB project : Development of an innovative control strategy for the integrated management of food pests. Project in partnership with Pr Mediouni Ben Jemâa Jouda , INRAT, Tunis.
  • 2020-2021 : FILAXTEXUS project : Production of textile flax fibres for open-end spinning by ultrasonic process and green sizing, public-private partnership the companies VRF and Textiles de Dunes. ADEME Graine.
  • 2019-2021 : ScreEnDex project : Screening of Dextrin Encapsulation capabilities / Application to gaseous pollutants and pharmaceutical molecules, public-private partnership with the company Roquette Frères within the framework of the CPER IRENE.
  • 2019-2021 : PCSI project : « Natural antimicrobials and insecticides encapsulated in biodegradable materials based on proteins, phospholipids and cyclodextrins for food preservation: applications to fresh orange juice and dates”. Collaboration with the Lebanese University, the University Claude Bernard Lyon 1 (LAGEP) and the University of Carthage, Tunisia.
  • 2019-2020 : AUF/CNRS Liban SCORE project : “Supramolecular Chelation of Heavy Metals and Radioactive Entities” (SCORE) Chelation supramoléculaire des métaux lourds et d’entités radioactives. (France, Tunisie, Liban).
  • 2018-2020 : PHC Galilé (N°39467XJ) : New supramolecular green solvent for VOC abatement. Partenaires :
    • Pr Andrea Mele, Politecnico di Milano, Milan, Italie.
    • Dr Margarida Costa-Gomes, Laboratoire de Chimie, ENS de Lyon, France.
  • 2017-2020 : ADEME GRAINE project « PHYTEO » : The production of essential oils: an eco-innovative way of reconverting historically polluted soils. Transversal project between 3 UCEIV teams, led by the IPCR team (Pr Anissa Hadj-Sahraoui).

Recent publications

 

  • L. Auezova, A. Najjar, M. Kfoury, S. Fourmentin, H. Greige-Gerges: Antibacterial activity of free or encapsulated selected phenylpropanoids against Escherichia coli and Staphylococcus epidermidis, J. Appl. Microbiol., 128, 710-720, 2020. DOI: 10.1111/jam.14516.
  • Z. Hammoud, R. Gharib, S. Fourmentin, A. Elaissari, H. Greige-Gerges : Drug-in-hydroxypropyl-b-cyclodextrin-in-lipoid S100/cholesterol liposomes: Effect of the characteristics of essential oil components on their encapsulation and release, Int. J. Pharm., 579, 119151, 2020. DOI:10.1016/j.ijpharm.2020.119151.
  • J. Eid, T. El Achkar, S. Fourmentin, L. Monticelli, H. Greige-Gerges, A. Jraij : First investigation of liposomes behavior and phospholipids organization in choline chloride-based deep eutectic solvents by atomic force microscopy, J. Mol. Liq., 2020. DOI:10.1016/j.molliq.2020.112851.
  • R. Gharib, J. Mediouni-Ben Jemâa, C. Charcosset, S. Fourmentin, H. Greige-Gerges: Retention of eucalyptol, a natural volatile insecticide, in delivery systems based on hydroxypropyl-b-cyclodextrin and liposomes, Eur. J. Lipid. Sci. Technol., 2020. DOI:10.1002/ejlt.201900402.
  • F. Fahri, K. Bacha, F.F. Chiki, J-P. Mbakidi, S. Panda, S. Bouquillon, S. Fourmentin: Air pollution: new biobased ionic liquids absorb both hydrophobic and hydrophilic volatile organic compounds with high efficiency, Environ. Chem. Lett. DOI:10.1007/s10311-020-01007-8.
  • A. Kasprowiak, F. Cazier-Dennin, P. Danjou, Flash chromatography system: a practical tool for demonstrating the influence of silica particles size on chromatographic separation, Journal of Chemical Education, 2020, acceptée. https://doi.org/10.1021/acs.jchemed.9b00929.
  • T. El Achkar, T. Moufawad, S. Ruellan, D. Landy, H. Greige-Gerges, S. Fourmentin: Cyclodextrins: from solute to solvent, Chem. Comm., 56, 3385-3388, 2020. DOI: 10.1039/D0CC00460J
  • E. Genty, C. Abou Serhal, R. El Khawaja, H. Dib, M. Labaki, I. Mallard, C. Poupin, S. Siffert, R. Cousin, Mixed Oxides Issued from Hydrotalcite Precursors for Toluene and CO Total Oxidation: Comparison of Preparation Method, Journal of Nanoscience and Nanotechnology, 20, 2020, 1130–1139. doi: 10.1166/jnn.2020.16978.
  • C. Musa, A. Kervoëlen, P. Danjou, A. Bourmaud, F. Delattre, Bio-based unidirectional composite made of flax fibre and isosorbide-based epoxy resin, Materials Letters, 258, 126818, 2020. https://doi.org/10.1016/j.matlet.2019.126818
  • N. AlHaddad, A. Rifai, A. Kasprowiak, F. Cazier-Dennin, P. Danjou, Water-insoluble phenoxycalix[4]pyrrole-epichlorohydrin polymer: synthesis, characterization and unexpected anions extraction from aqueous solutions, Organic & Biomolecular Chemistry, 17, 2019, 7330-7336. https://doi.org/DOI:10.1039/C9OB01306G
  • A. Rifai, N. AlHaddad, M. Noun, I. Abbas, M. Tabbal, R. Chatila, F. Cazier-Dennin, P. Danjou, A click mediated route to a novel fluorescent pyridino-extended calix[4]pyrrole sensor: synthesis and binding studies, Organic & Biomolecular Chemistry, 17, 2019, 5818-5825. https://doi.org/10.1039/C9OB01106D
  • C. Moitessier, A. Rifai, P. Danjou, I. Mallard, F. Cazier-Dennin, Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: Toward the emergence of new building blocks, Beilstein Journal of Organic Chemistry, 15, 2019, 721-726. https://doi.org/10.3762/bjoc.15.67
  • C. Musa, P. Danjou, A. Pauwels, F. Cazier-Dennin, F. Delattre, Ultrasound-Assisted Heterogeneous Synthesis of Bio-Based Oligo-Isosorbide Glycidyl Ethers: Towards Greener Epoxy Precursors, Molecules, 24, 2019, 1643. https://doi.org/10.3390/molecules24091643
  • G. Colombo Dugoni, M. E. Di Pietro, M. Ferro, F. Castiglione, S. Ruellan, T. Moufawad, L. Moura, M. F. Costa Gomes, S. Fourmentin, and A. Mele : Effect of water on DES/b-cyclodextrin systems, ACS Sustainable Chem.Eng.,7, 7277-7285, 2019. DOI: 10.1021/ acssuschemeng.9b00315.
  • G. Crini, N. Morin-Crini, M. Fourmentin, S. Fourmentin, G. Torri : Synthesis of silica materials containing cyclodextrin and their applications in wastewater treatment, Environ. Chem. Lett., 17, 683-696, 2019. DOI:10.1007/s10311-018-00818-0.
  • M Kfoury, L. Auezova, H. Greige-Gerges, S. Fourmentin : Encapsulation in cyclodextrins to widen the applications of essential oils, Environ. Chem. Lett.,17(1), 129-143, 2019. DOI:10.1007/s10311-018-0783-y
  • Z. Hammoud, R. Gharib, S. Fourmentin, A. Elaissari, H. Greige-Gerges : New findings on the incorporation of essential oil components into liposomes made of lipoid S100 and cholesterol, Int. J. Pharm., 2019. DOI:10.1016/j.ijpharm.2019.02.022.
  • T. Moufawad, L.Moura, M. Ferreira, H. Bricout, S. Tilooy, E. Monflier, M. Costa Gomes, D. Landy, S.  Fourmentin : First evidence of cyclodextrin inclusion complexes in a deep eutectic solvent, ACS Sustain. Chem. Eng., 2019. DOI:10.1021/acssuschemeng.9b00044.
  • M. Kfoury, C. Geagea, S. Ruellan, H. Greige-Gerges, S. Fourmentin: Effect of cyclodextrin and cosolvent on the solubility and antioxidant activity of caffeic acid, Food Chem., 278, 163-169, 2019DOI:10.1016/j.foodchem.2018.11.055.
  • R. Gharib, S. Haydar, C. Charcosset, S. Fourmentin, H. Greige-Gerges : First study on the release of a natural antimicrobial agent, estragole, from freeze-dried delivery systems based on cyclodextrins and liposomes., J. Drug. Deliv. Sci. Technol., 52, 794-802, 2019. DOI:10.1016/j.jddst.2019.05.032.
  • M. Ben Abada, S. Haouel Hamdi, R. Gharib, C. Masseoud, S. Fourmentin, H. Greige-Gerges, J. Mediouni Ben Jemâa: Postharvest management control of Ectomyelois ceratoniae (Pyralidae): New insights through essential oil encapsulation in cyclodextrin, Pest Manag. Sci., 2019DOI:10.1002/ps.5315.
  • T. El Achkar, S. Fourmentin, H. Greige-Gerges : Deep Eutectic Solvents: an overview on their interactions with water and biochemical compounds, J. Mol. Liq., 288, 111028, 2019. DOI:10.1016/j.molliq.2019.111028.
  • M.E. Di Pietro, G. Colombo Dugoni, M. Ferro, A. Mannu, F. Castiglione, M. Costa Gomes, S. Fourmentin, A. Mele: Do Cyclodextrins Encapsulate Volatiles in Deep Eutectic Systems? ACS Sustain. Chem. Eng., 7, 17397-17405, 2019. DOI:10.1021/acssuschemeng.9b04526.
  • L. Cisse, A. Djande, M. Capo‐Chichi, A. Khonte, J.‐P. Bakhoum, F. Delattre, J. Yoda, A. Saba, A. Tine, J.‐J. Aaron, Quantitative study of the substituent effects on the electronic absorption and fluorescence spectra of coumarins, J. Phys. Org. Chem., 2019, DOI: 10.1002/poc.4014.
  • A. Ivanov, C. Falaise, K. Laouer, F. Hache, P. Changenet, Y. Mironov, D. Landy, Y. Molard, S. Cordier, M. Shestopalov, M. Haouas, E. Cadot : Size-Exclusion Mechanism Driving Host-Guest Interactions between Octahedral Rhenium Clusters and Cyclodextrins, Inorg. Chem., 58 (19), 13184-13194, 2019. DOI: 10.1021/acs.inorgchem.9b02048
  • A. Ivanov, C. Falaise, D. Landy, M. Haouas, Y. Mironov, M. Shestopalov, E. Cadot : Tuning the chaotropic effect as an assembly motif through one-electron transfer in a rhenium cluster, Chem. Commun., 55 (67), 9951-9954, 2019. DOI: 10.1039/c9cc05136h
  • M. Diab, S. Floquet, M. Haouas, P. Abramov, X. Lopez, D. Landy, A. DAamond, C. Falaise, V. Guérineau, D. Touboul, D. Naoufal, E. Cadot : Encapsulation of Chaotropic closo-Decahydrodecaborate Clusters Within Cyclodextrins: Synthesis, Solution Studies, and DFT Calculations, Eur. J. Inorg. Chem., 2019 (29), 3373-3382, 2019. DOI: 10.1002/ejic.201900602
  • C. Abou Serhal, I. Mallard, C. Poupin, M. Labki, S. Siffert, R. Cousin : Effect of microwave irradiations parameters on Co/Fe nanocatalysts for the total oxidation of VOCs. Eur. J.I.C. 27, 3218-3227, 2019. DOI : 10.1002/ejic. 201801528
  • M. Kfoury, D. Landy, S. Fourmentin: Contribution of headspace to the analysis of cyclodextrin inclusion complexes, J. Incl. Phenom. Macro. Chem.,93, 19-32, 2019. DOI:10.1007/s10847-018-0818-9.