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.
  • Chimie, Structures, Propriétés de Biomatériaux et d’Agents Thérapeutiques, UMR CNRS 7244, Université Paris 13.
  • Laboratoire de Chimie, ENS Lyon.

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

Khemesse Kital

2015-2018

Characterization of biogenic ortho phthalaldehyde amine complexes by Nuclear Magnetic Resonance and molecular fluorescence.

Corentin Musa

2016-2019

Elaboration by sonochemistry and characterization of biosourced composite materials based on mucilaginous bioadhesives and flax fibers

Tarek Moufawad

2016-2019

Development of new washing solvents for VOC absorption

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

Research agreement

  • 2019 : COVSOLV, SFR Condorcet project :  Absorption of volatile compounds via eco-compatible solvents. Collaboration with the Institut de Chimie Moléculaire de Reims (ICMR), UMR 7312, University of Reims Champagne Ardenne (URCA).
  • 2019-2020 : SCORE AUF/CNRS Liban Project : Supramolecular Chelation of Heavy Metals and Radioactive Entities (SCORE) (France, Tunisie, Liban).
  • 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, Claude Bernard Lyon 1 University (LAGEP) and the University of Carthage, Tunisia.
  • 2017-2019 : ULTRAFLAX : Design of new bio-composite materials for eco-design based on the mucilage of oilcake and short flax fibres.
  • 2018 IRENE Project: Characterization of new materials with microencapsulated phase change.
  • 2018 : IRENE Project (REMELO) : Synthesis and study of new complexing entities based on calix[4]pyrrole for the decontamination of aquatic environments with heavy metals.
  • 2016-2018 : PCSI Project :  Improvement of nutritional qualities of food by encapsulation of active compounds: application to estragole. Collaboration with the Lebanese University, the Claude Bernard Lyon 1 University (LAGEP) and the University of Carthage, Tunisia.
  • 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 Lyon, France.
  • 2018 : SFR Condorcet Project : « Use of ultrasonic and enzymatic processes to improve the quality of flax fibres”. Collaboration with REIMS University, UMR INRA 614 FARE (URCA).
  • 2018-2019 : BQR A2U : Study of the encapsulation properties of amphiphilic cyclodextrins in deep eutectic solvents and the conditions of the possibility of their industrial and commercial valorization. Partners :
    • LG2A UMR CNRS 7378
    • UCCS UMR CNRS 8181
    • Curapp-ESS, UMR CNRS 7319

Recent publications

  • Corentin Musa, Antoine Kervoëlen, Pierre-Edouard Danjou, Alain Bourmaud, François Delattre, Bio-based unidirectional composite made of flax fibre and isosorbide-based epoxy resin, Materials Letters, accepted, 2019. https://doi.org/10.1016/j.matlet.2019.126818
  • Nancy AlHaddad, Ahmad Rifai, Amaury Kasprowiak, Francine Cazier-Dennin, Pierre-Edouard 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
  • Ahmad Rifai, Nancy AlHaddad, Manal Noun, Ismail Abbas, Malek Tabbal, Rania Chatila, Francine Cazier-Dennin, Pierre-Edouard 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
  • Clémence Moitessier, Ahmad Rifai, Pierre-Edouard Danjou, Isabelle Mallard, Francine 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
  • Corentin Musa, Pierre-Edouard Danjou, Antoine Pauwels, Francine Cazier-Dennin, François 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., Just Accepted Manuscript, 2019. DOI: 10.1021/ acssuschemeng.9b00315.
  • 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.
  • 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.
  • 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., 78, 1-23, 2018. DOI:10.1016/j.progpolymsci.2017.07.004.
  • E. Oliva, D. Mathiron, E. Bertaut, D. Landy, D. Cailleu, S. Pilard, C. Clement, E. Courot, V. Bonnet, F. Djedaïni-Pilard : Physico-chemical studies of resveratrol, methyl-jasmonate and cyclodextrin interactions: an approach to resveratrol bioproduction optimization. RSC Adv., 8, 1528-1538, 2018. DOI :10.1039/C7RA11619E
  • R. Gharib, S. Fourmentin, C. Charcosset, H. Greige-Gerges : Effect of hydroxypropyl-ß–cyclodextrin on lipid membrane fluidity, stability and freeze-drying of liposomes. J. Drug. Deliv. Sci. Technol., 44, 101-107, 2018. DOI: 10.1016/j.jddst.2017.12.009.
  • J. Azzi, L. Auezova, P-E Danjou, S. Fourmentin, H. Greige-Gerges: First evaluation of drug-in-cyclodextrin-in-liposomes as encapsulating system for nerolidol, Food. Chem., 255, 399-404, 2018. DOI:10.1016/j.foodchem.2018.02.055.
  • J. Azzi, A. Jraij, L. Auezova, S. Fourmentin, H. Greige-Gerges : Novel findings for quercetin encapsulation and preservation with cyclodextrins, liposomes, and drug-in-cyclodextrin-in-liposomes. Food Hydrocoll., 81, 328-340, 2018. DOI:10.1016/j.foodhyd.2018.03.006
  • R. Gharib, H. Greige-Gerges, S. Fourmentin, C. Charcosset: Hydroxypropyl b-cyclodextrin as membrane protectant during freeze-drying of hydrogenated and non-hydrogenated liposomes and molecule-in-cyclodextrin-in-liposomes: application to trans-anethole. Food. Chem., 267, 67-74, 2018. DOI:10.1016/j.foodchem.2017.10.144
  • I. Delsarte, F, Delattre, C. Rafin, E. Veignie : Investigations of benzo[a]pyrene encapsulation and Fenton degradation by starch nanoparticles. Carbohydr. Polym., 186, 344-349, 2018. DOI:10.1016/j.carbpol.2018.01.037.
  • I. Mallard, D. Bourgeois, S. Fourmentin: A friendly environmental approach for the controlled release of Eucalyptus essential oil. Colloids Surf. A Physicochem. Eng. Asp., 549, 130–137, 2018. DOI:10.1016/j.colsurfa.2018.04.010.
  • M. Kfoury, D. Landy, S. Fourmentin : Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review, Molecules, 23, 1204-1226, 2018. doi:10.3390/molecules23051204.
  • G. Crini, S. Fourmentin, E. Fenyvesi, G. Torri, M. Fourmentin, N. Morin-Crini : Cyclodextrins, from molecules to applications, Environ. Chem. Lett., 2018. DOI:10.1007/s10311-018-0763-2.