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1. Chiral Quantum Metamaterial for Hypersensitive Biomolecule Detection

Author

Maryam Hajji, Martin Kartau, Graeme Cooke, William J. Peveler, Cameron Gilroy, Malcolm Kadodwala, Michele Cariello, Christopher D. Syme, Aurélie Malfait, Nikolaj Gadegaard, Affar S. Karimullah, Patrice Woisel, Unité Matériaux et Transformations - UMR 8207 (UMET), Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), and Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)

Subjects
General Physics and Astronomy, Physics::Optics, quantum dots, 02 engineering and technology, 010402 general chemistry, quantum metamaterials, 01 natural sciences, plasmonics, Nanotechnology, General Materials Science, Quantum metamaterial, Quantum, Circular polarization, Plasmon, Physics, chemistry.chemical_classification, business.industry, Biomolecule, General Engineering, Metamaterial, Stereoisomerism, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, superchirality, 0104 chemical sciences, chiral, [CHIM.POLY]Chemical Sciences/Polymers, Orders of magnitude (time), chemistry, Pharmaceutical Preparations, Semiconductors, Quantum dot, Optoelectronics, 0210 nano-technology, business
Abstract

International audience; Chiral biological and pharmaceutical molecules are analyzed with phenomena that monitor their very weak differential interaction with circularly polarized light. This inherent weakness results in detection levels for chiral molecules that are inferior, by at least six orders of magnitude, to the single molecule level achieved by state-of-the-art chirally insensitive spectroscopic measurements. Here, we show a phenomenon based on chiral quantum metamaterials (CQMs) that overcomes these intrinsic limits. Specifically, the emission from a quantum emitter, a semiconductor quantum dot (QD), selectively placed in a chiral nanocavity is strongly perturbed when individual biomolecules (here, antibodies) are introduced into the cavity. The effect is extremely sensitive, with six molecules per nanocavity being easily detected. The phenomenon is attributed to the CQM being responsive to significant local changes in the optical density of states caused by the introduction of the biomolecule into the cavity. These local changes in the metamaterial electromagnetic environment, and hence the biomolecules, are invisible to “classical” light-scattering-based measurements. Given the extremely large effects reported, our work presages next generation technologies for rapid hypersensitive measurements with applications in nanometrology and biodetection.

Published
2021
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2. Supramolecular Hydrogels with Tunable Swelling by Host complexation with Cyclobis (paraquat- p -phenylene)

Author

François Stoffelbach, Richard Hoogenboom, Joel Lyskawa, Dominique Hourdet, Jonathan Potier, Khaled Belal, Graeme Cooke, Patrice Woisel, Lieselot De Smet, Alba Marcellan, Aurélien Vebr, Unité Matériaux et Transformations - UMR 8207 (UMET), Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Sciences et Ingénierie de la Matière Molle (UMR 7615) (SIMM), Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Universiteit Gent = Ghent University (UGENT), University of Glasgow, Estonian Research CouncilEuropean Commission, Region Hauts-de-France, ANR-12-BS08-0005,STRAPA,Assemblages multistimulables de polymères dans l'eau(2012), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Centrale Lille Institut (CLIL), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), and Universiteit Gent = Ghent University [Belgium] (UGENT)

Subjects
Polymers and Plastics, Supramolecular chemistry, macromolecular substances, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, supramolecular chemistry, Inorganic Chemistry, chemistry.chemical_compound, [SPI]Engineering Sciences [physics], Pulmonary surfactant, Polymer chemistry, Materials Chemistry, medicine, [CHIM]Chemical Sciences, Sodium dodecyl sulfate, hydrogels, chemistry.chemical_classification, Aqueous solution, Organic Chemistry, technology, industry, and agriculture, 021001 nanoscience & nanotechnology, 0104 chemical sciences, chemistry, tunable swelling, Self-healing hydrogels, host-guest complexation, Counterion, Swelling, medicine.symptom, 0210 nano-technology, Cyclobis(paraquat-p-phenylene), [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft]
Abstract

Controlling the swelling properties of hydrogels is of primary importance for many applications ranging from actuators and valves to tissue engineering and drug delivery. Herein, we report the use of cyclobis(paraquat-p-phenylene) (CBPQT4+,4X–) as a versatile host to fine-tune the swelling behavior of 1,5-dialkyloxynaphthalene guest containing poly(N,N-dimethylacrylamide) hydrogels (NaphtGelz) through supramolecular host–guest complexation. While the equilibrium swelling of NaphtGelz in water decreases with increasing amount of hydrophobic naphthalene groups, the opposite behavior is observed with superabsorbing behavior (up to 180 times their initial dry mass) upon immersion in aqueous solutions containing the macrocyclic CBPQT4+,4X– due to formation of tetracationic host–guest complexes. In this case, the swelling amplitude could be conveniently programmed either by variation of the naphthalene content of the hydrogels or by controlling the stoichiometry of the host–guest binding events. Furthermore, by modifying the nature of the counterions (X = Cl–, Br–, and I–) of the tetracationic CBPQT4+ macrocyclic host, the swelling of the hydrogels could be tuned in line with Pearson’s absolute hardness scale of X–. The swelling behavior of these supramolecular hydrogels could be successfully described by a theoretical model, taking into account the hydrophobic association of the naphthalene groups and their screening by host–guest complexation. Finally, addition of sodium dodecyl sulfate as a surfactant to the supramolecularly swollen hydrogels led to a large decrease in hydrogel size due to dissociation of the host–guest complexes and the formation of CBPQT4+,4DS– within the hydrogel.

Published
2021
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3. Supramolecular polymer hydrogels induced by host–guest interactions with di-[cyclobis(paraquat-p-phenylene)] cross-linkers: from molecular complexation to viscoelastic properties

Author

Khaled Belal, Dominique Hourdet, Hui Guo, Patrice Woisel, Matthieu Fumagalli, Alba Marcellan, Graeme Cooke, François Stoffelbach, Sciences et Ingénierie de la Matière Molle (SIMM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Ingénierie des Systèmes Polymères, Unité Matériaux et Transformations - UMR 8207 (UMET), Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), WestCHEM, University of Glasgow, Centre National de la Recherche Scientifique (CNRS)-PSL Research University (PSL)-ESPCI ParisTech-Université Pierre et Marie Curie - Paris 6 (UPMC), Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), and Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)

Subjects
chemistry.chemical_classification, Supramolecular chemistry, 02 engineering and technology, General Chemistry, Polymer, 010402 general chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 01 natural sciences, Dissociation (chemistry), 0104 chemical sciences, Supramolecular polymers, chemistry.chemical_compound, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Self-healing hydrogels, Polymer chemistry, Copolymer, Molecule, 0210 nano-technology, Cyclobis(paraquat-p-phenylene), [PHYS.COND.CM-SCM]Physics [physics]/Condensed Matter [cond-mat]/Soft Condensed Matter [cond-mat.soft]
Abstract

International audience; Supramolecular polymer networks have been designed on the basis of a π-electron donor/acceptor complex: naphthalene (N)/cyclobis(paraquat-p-phenylene) (CBPQT4+ = B). For this purpose, a copolymer of N,N-dimethylacrylamide P(DMA-N1), lightly decorated with 1 mol% of naphthalene pendant groups, has been studied in semi-dilute un-entangled solution in the presence of di-CBPQT4+ (BB) crosslinker type molecules. While calorimetric experiments demonstrate the quantitative binding between N and B groups up to 60 °C, the introduction of BB crosslinkers into the polymer solution gives rise to gel formation above the overlap concentration. From a comprehensive investigation of viscoelastic properties, performed at different concentrations, host/guest stoichiometric ratios and temperatures, the supramolecular hydrogels are shown to follow a Maxwellian behavior with a strong correlation of the plateau modulus and the relaxation time with the effective amount of interchain cross-linkers and their dissociation dynamics, respectively. The calculation of the dissociation rate constant of the supramolecular complex, by extrapolation of the relaxation time of the network back to the beginning of the gel regime, is discussed in the framework of theoretical and experimental works on associating polymers.

Published
2017
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4. Synthesis, binding and self-assembly properties of a well-defined pillar[5]arene end functionalised polydimethylacrylamide

Author

Steven Ruellan, Jean-Michel Guigner, Graeme Cooke, Joel Lyskawa, François Delattre, François Stoffelbach, Patrice Woisel, Nérimel Laggoune, Unité Matériaux et Transformations - UMR 8207 (UMET), Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV), Université du Littoral Côte d'Opale (ULCO), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de minéralogie, de physique des matériaux et de cosmochimie (IMPMC), Muséum national d'Histoire naturelle (MNHN)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de recherche pour le développement [IRD] : UR206-Centre National de la Recherche Scientifique (CNRS), GCPOC - WestCHEM (GCPOC), GCPOC - WestCHEM, Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), Unité de chimie environnementale et interactions sur le vivant (UCEIV), Université du Littoral Côte d'Opale, Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC), Institut de recherche pour le développement [IRD] : UR206-Centre National de la Recherche Scientifique (CNRS)-Muséum national d'Histoire naturelle (MNHN)-Université Pierre et Marie Curie - Paris 6 (UPMC), Université de Lille, ENSCL, CNRS, INRA, Unité Matériaux et Transformations - UMR 8207 [UMET], Unité de Chimie Environnementale et Interactions sur le Vivant [UCEIV], Institut Parisien de Chimie Moléculaire [IPCM], and Institut de minéralogie, de physique des matériaux et de cosmochimie [IMPMC]

Subjects
Chloroform, Polymers and Plastics, Organic Chemistry, Bioengineering, Raft, Biochemistry, Chloride, chemistry.chemical_compound, Polymerization, chemistry, Polymer chemistry, medicine, Moiety, Molecule, Organic chemistry, [CHIM]Chemical Sciences, Self-assembly, Solubility, medicine.drug
Abstract

International audience; The synthesis, binding and self-assembly properties of a well-defined pillar[5]arene end-functionalised poly(dimethylacrylamide)(MePilla-PDMAC) are reported. In order to synthesise MePilla-PDMAC, a new trithiocarbonate type RAFT agent MePilla-CTA was developed incorporting a partially methylated pillar[5]-arene moiety. Kinetic studies clearly indicated the propensity of MePilla-CTA to control the polymeri-sation of DMAC. Interestingly, as PDMAC type chains display good solubilty both in organic and aqueous media, MePilla-PDMAC was able of specifically bind electron deficient guest molecules at the α-chain-end both in chloroform and water. Complex formation was found to be reversible upon addition of chloride anions or heating in organic and aqueous media, respectively. Furthermore, cryo-TEM, VT-NMR (1 H) and VT-DLS investigations also indicated the ability of MePilla-PDMAC to self-assemble into micelle-like aggregates in water showing reversible recognition properties.

Published
2015
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5. Programmable Polymer-Based Supramolecular Temperature Sensor with a Memory Function

Author

François Delattre, Graeme Cooke, Joel Lyskawa, Patrice Woisel, Marc Bria, François Stoffelbach, Victor Retamero De La Rosa, Léna Sambe, Richard Hoogenboom, Khaled Belal, Unité Matériaux et Transformations - UMR 8207 (UMET), Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL), Universiteit Gent = Ghent University [Belgium] (UGENT), Chimie des polymères (LCP), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV), Université du Littoral Côte d'Opale (ULCO), WestCHEM, University of Glasgow, Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), Ghent University [Belgium] (UGENT), Institut Parisien de Chimie Moléculaire (IPCM), Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie environnementale et interactions sur le vivant (UCEIV), Université du Littoral Côte d'Opale, Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Universiteit Gent = Ghent University (UGENT), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Phase transition, Materials science, Polymers, Thermometers, Proton Magnetic Resonance Spectroscopy, Supramolecular chemistry, 010402 general chemistry, Lower critical solution temperature, 01 natural sciences, Catalysis, Polymer chemistry, Copolymer, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Cyclodextrin, 010405 organic chemistry, Transition temperature, General Chemistry, Polymer, General Medicine, 0104 chemical sciences, Hysteresis, chemistry, Chemical engineering, Spectrophotometry, Ultraviolet
Abstract

A new class of polymeric thermometers with a memory function is reported that is based on the supramolecular host-guest interactions of poly(N-isopropylacrylamide) (PNIPAM) with side-chain naphthalene guest moieties and the tetracationic macrocycle cyclobis(paraquat-p-phenylene) (CBPQT(4+)) as the host. This supramolecular thermometer exhibits a memory function for the thermal history of the solution, which arises from the large hysteresis of the thermoresponsive LCST phase transition (LCST = lower critical solution temperature). This hysteresis is based on the formation of a metastable soluble state that consists of the PNIPAM-CBPQT(4+) host-guest complex. When heated above the transition temperature, the polymer collapses, and the host-guest interactions are disrupted, making the polymer more hydrophobic and less soluble in water. Aside from providing fundamental insights into the kinetic control of supramolecular assemblies, the developed thermometer with a memory function might find use in applications spanning the physical and biological sciences.

Published
2014
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6. Elaboration of Thermoresponsive Supramolecular Diblock Copolymers in Water from Complementary CBPQT ^\textrm4+ and TTF End-Functionalized Polymers

Author

François Stoffelbach, Marc Bria, Patrice Woisel, Graeme Cooke, Aurélie Malfait, Joel Lyskawa, Katarzyna Poltorak, Léna Sambe, Unité Matériaux et Transformations - UMR 8207 (UMET), Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), Chimie des polymères (LCP), Institut Parisien de Chimie Moléculaire (IPCM), Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), WestCHEM, University of Glasgow, Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Azides, Materials science, Polymers and Plastics, Polymers, Acrylic Resins, Supramolecular chemistry, 010402 general chemistry, 01 natural sciences, Lower critical solution temperature, Catalysis, Phase Transition, Polymerization, chemistry.chemical_compound, Heterocyclic Compounds, Polymer chemistry, Materials Chemistry, Copolymer, [CHIM]Chemical Sciences, Reversible addition−fragmentation chain-transfer polymerization, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Cycloaddition Reaction, 010405 organic chemistry, Organic Chemistry, Temperature, Water, Polymer, Cycloaddition, 0104 chemical sciences, chemistry, Alkynes, Proton NMR, Hydrophobic and Hydrophilic Interactions, Copper, Tetrathiafulvalene
Abstract

A well-defined poly(N-isopropyl acrylamide) 1 incorporating at one termini a cyclobis(paraquat-p-phenylene) (CBPQT(4+)) recognition unit is prepared via a RAFT polymerization followed by a copper-catalyzed azide-alkyne cycloaddition (CuAAC). (1)H NMR (1D, DOSY), UV-vis and ITC experiments reveal that polymer 1 is able of forming effective host-guest complexes with tetrathiafulvalene (TTF) end-functionalized polymers in water, thereby leading to the formation of non-covalently-linked double-hydrophilic block copolymers. The effect of the temperature on both the LCST phase transition of 1 and its complexes and on CBPQT(4+)/TTF host-guest interactions is investigated.

Published
2014
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7. Protein-mediated dethreading of a biotin-functionalised pseudorotaxane

Author

Gouher Rabani, Alan Cooper, Belal Khaled, Stuart T. Caldwell, Vincent M. Rotello, Brian Fitzpatrick, Margaret Nutley, Brian O. Smith, Patrice Woisel, Mathis O. Riehle, Catherine Elaine Maclean, Graeme Cooke, University of Glasgow, Department of Chemistry [Amherst], University of Massachusetts [Amherst] (UMass Amherst), University of Massachusetts System (UMASS)-University of Massachusetts System (UMASS), Unité Matériaux et Transformations - UMR 8207 (UMET), Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL), Université de Lille, ENSCL, CNRS, INRA, Unité Matériaux et Transformations - UMR 8207 [UMET], and Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)

Subjects
Models, Molecular, Rotaxanes, Stereochemistry, Biotin, Naphthalenes, Biochemistry, Fluorescence spectroscopy, [SPI.MAT]Engineering Sciences [physics]/Materials, chemistry.chemical_compound, Moiety, QD, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, Physical and Theoretical Chemistry, Naphthalene, Benzoic acid, biology, Molecular Structure, Organic Chemistry, NeutrAvidin, [CHIM.MATE]Chemical Sciences/Material chemistry, Avidin, Combinatorial chemistry, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, biology.protein, Proton NMR
Abstract

International audience; In this article, we describe the synthesis of new biotin-functionalised naphthalene derivatives 3 and 4 and their complexation behaviour with avidin and neutravidin using a range of analytical techniques. We have shown using 2-(4′-hydroxyazobenzene)benzoic acid displacement and ITC experiments, that compounds 3 and 4 have the propensity to form reasonably high-affinity bioconjugates with avidin and neutravidin. We have also demonstrated using 1H NMR, UV-vis and fluorescence spectroscopy that the naphthalene moiety of 3 and 4 facilitates the formation of pseudorotaxane-like structures with 1 in water. We have then investigated the ability of avidin and neutravidin to modulate the complexation between 1 and 3 or 4. UV-vis and fluorescence spectroscopy has shown that in both cases the addition of the protein disrupts complexation between the naphthalene moieties of 3 and 4 with 1.

Published
2014
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8. Multi-stimuli responsive supramolecular diblock copolymers

Author

François Stoffelbach, K. Belal, Vincent Humblot, Marc Bria, Léna Sambe, Joel Lyskawa, F. X. Sauvage, Michel Sliwa, François Delattre, Patrice Woisel, Bernadette Charleux, Graeme Cooke, Unité Matériaux et Transformations - UMR 8207 (UMET), Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL), Chimie des polymères (LCP), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Unité de Chimie Environnementale et Interactions sur le Vivant (UCEIV), Université du Littoral Côte d'Opale (ULCO), Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 (LASIRE), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Centrale Lille Institut (CLIL), Laboratoire de Réactivité de Surface (LRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265 (C2P2), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École supérieure de Chimie Physique Electronique de Lyon (CPE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Glasgow Centre for Physical Organic Chemistry, University of Glasgow, Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), Institut Parisien de Chimie Moléculaire (IPCM), Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Unité de chimie environnementale et interactions sur le vivant (UCEIV), Université du Littoral Côte d'Opale, Laboratoire de Spectrochimie Infrarouge et Raman - UMR 8516 (LASIR), Centre National de la Recherche Scientifique (CNRS)-Université de Lille, Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Université de Lyon-Université de Lyon-École supérieure de Chimie Physique Electronique de Lyon (CPE)-Centre National de la Recherche Scientifique (CNRS), Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS), and Université de Lyon-Université de Lyon-École Supérieure de Chimie Physique Électronique de Lyon (CPE)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Acrylate, Materials science, Polymers and Plastics, 010405 organic chemistry, Organic Chemistry, Supramolecular chemistry, Bioengineering, Chain transfer, 010402 general chemistry, 01 natural sciences, Biochemistry, Redox, Combinatorial chemistry, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, chemistry, Polymer chemistry, Copolymer, Moiety, Reversible addition−fragmentation chain-transfer polymerization, Macromolecule
Abstract

A well-defined cyclobis(paraquat-p-phenylene) (CBPQT4+) end-functionalized poly(n-butyl acrylate) 3 was prepared via RAFT polymerization using a new trithiocarbonate CBPQT4+ derivative 2 as a reversible chain transfer agent. We have shown that the electron-poor CBPQT4+ moiety at the α-chain-end could be specifically modified by complex formation with various functionalized macromolecules featuring complementary electron rich end groups, thereby leading to the corresponding supramolecular diblock copolymers. The latter could be conveniently disassembled upon heating, by applying electrochemical redox processes or by the addition of a competing molecular guest. Furthermore, we can generate new diblock architectures upon the addition of an appropriately functionalized polymer. We also describe preliminarily results regarding the formation of nanostructured architectures both in solution and in thin films.

Published
2014
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9. Optical and electrochemical properties of tunable host-guest complexes linked to plasmonic interfaces

Author

Ophélie Saison, Rabah Boukherroub, Joel Lyskawa, Léna Sambe, Sabine Szunerits, Xavier Castel, Joanna Niedziółka-Jönsson, Abdellatif Akjouj, Yan Pennec, Fatiha Barka-Bouaifel, Bahram Djafari-Rouhani, Graeme Cooke, Nacer Bezzi, Patrice Woisel, Institut de Recherche Interdisciplinaire [Villeneuve d'Ascq] (IRI), Université de Lille, Sciences et Technologies-Université de Lille, Droit et Santé-Centre National de la Recherche Scientifique (CNRS), LTMGP, Université Abderrahmane Mira [Béjaïa], Institut d'Electronique et de Télécommunications de Rennes (IETR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-SUPELEC-Centre National de la Recherche Scientifique (CNRS), Institut d’Électronique, de Microélectronique et de Nanotechnologie (IEMN) - UMR 8520 (IEMN), Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Université Polytechnique Hauts-de-France (UPHF)-Ecole Centrale de Lille-Université Polytechnique Hauts-de-France (UPHF)-Institut supérieur de l'électronique et du numérique (ISEN), Unité Matériaux et Transformations - UMR 8207 (UMET), Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut National de la Recherche Agronomique (INRA), GCPOC - WestCHEM (GCPOC), GCPOC - WestCHEM, Centre National de la Recherche Scientifique (CNRS)-Université de Lille, Droit et Santé-Université de Lille, Sciences et Technologies, Centre National de la Recherche Scientifique (CNRS)-Ecole Supérieure d'Electricité - SUPELEC (FRANCE)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), Institut d’Électronique, de Microélectronique et de Nanotechnologie - UMR 8520 (IEMN), Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF), Institut de Chimie du CNRS (INC)-Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille-Ecole Nationale Supérieure de Chimie de Lille (ENSCL), University of Glasgow, Laboratoire de Technologie des Matériaux et de Génie des Procédés (LTMGP), NanoBioInterfaces - IEMN (NBI - IEMN), Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF)-Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Supérieure d'Electricité - SUPELEC (FRANCE)-Centre National de la Recherche Scientifique (CNRS), and Institut National de la Recherche Agronomique (INRA)-Ecole Nationale Supérieure de Chimie de Lille (ENSCL)-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)

Subjects
Nanotechnology, [CHIM.MATE]Chemical Sciences/Material chemistry, 02 engineering and technology, General Chemistry, Substrate (electronics), 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, chemistry, X-ray photoelectron spectroscopy, Materials Chemistry, Molecule, Surface plasmon resonance, Cyclic voltammetry, 0210 nano-technology, Plasmon, Tetrathiafulvalene, ComputingMilieux_MISCELLANEOUS, Cyclophane
Abstract

International audience; This article describes the use of localized surface plasmon resonance (LSPR) interface to detect complexation/decomplexation steps of a controllable host–guest system at the solid–liquid interface. The LSPR interfaces consist of a sandwiched structure comprising a tin-doped indium oxide (ITO) substrate, gold nanostructures (Au NSs) and a thin ITO film overcoating. “Click” chemistry was used to covalently link an alkyne-functionalized π-electron deficient tetracationic cyclophane cyclobis(paraquat-p-phenylene) (CBPQT4+) unit to an azide-terminated LSPR interface. The modified interfaces were characterized using X-ray photoelectron spectroscopy (XPS), cyclic voltammetry and UV-vis transmission spectroscopy. Tetrathiafulvalene (TTF) was used as a model guest molecule to demonstrate the possibility to follow the complexation/decomplexation events by monitoring the change in the LSPR signal. The results demonstrate that redox controlled host–guest complexation at the surface can be monitored effectively using LSPR.

Published
2011
Full Text
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