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Ivan Jabin - One of the best experts on this subject based on the ideXlab platform.
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Use of Calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties
Organic and Biomolecular Chemistry, 2020Co-Authors: Ludovic Troian-gautier, Alice Mattiuzzi, Olivia Reinaud, Corinne Lagrost, Ivan JabinAbstract:Surface modification represents an active field of research that finds applications, amongst others, in the development of medical devices, sensors and biosensors, anti-biofouling materials, self-cleaning surfaces, surfaces with controlled wettability, corrosion resistance, heterogeneous catalysis and microelectronics. For some applications, surface functionalization with a nanometric-size monolayer is desired. In this review, efforts to covalently functionalize a wide array of surfaces with Calixarenes bearing diazonium groups are described. More specifically, methodologies to obtain monolayers of calix[4 or 6]arene derivatives on conductive, semi-conductive or insulating surfaces as well as on nanoparticles are presented. The main advantages of this general surface modification strategy (i.e. formation of true monolayers that can be post-functionalized, high robustness and control over the composition of the Calixarene-based coating) and its current scope of applications and future challenges are discussed.
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Calixarene-based Stationary Phases for Chromatography
Current Organic Chemistry, 2015Co-Authors: Guillaume Delahousse, Roy Lavendomme, Ivan Jabin, Valérie Agasse, Pascal CardinaelAbstract:Due to their easy functionalization and their unique conformational and recognition properties, Calixarenes are attracting molecular platforms for the elaboration of separation systems. Thus, in the last decades, these macrocyclic compounds have been subject to extensive research in analytical chemistry. This review is focused on the use of Calixarenes as selectors in the chromatographic separation field. The structures of Calixarene derivatives and their applications as stationary phases for gas chromatography as well as high-performance liquid chromatography are described.
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Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization.
Nature Communications, 2012Co-Authors: Alice Mattiuzzi, Ivan Jabin, Olivia Reinaud, Claire Mangeney, Clément Roux, Luis Santos, Jean-françois Bergamini, Philippe Hapiot, Corinne LagrostAbstract:An essential issue in the development of materials presenting an accurately functionalized surface is to achieve control of layer structuring. Whereas the very popular method based on the spontaneous adsorption of alkanethiols on metal faces stability problems, the reductive electrografting of aryldiazonium salts yielding stable interface, struggles with the control of the formation and organization of monolayers. Here we report a general strategy for patterning surfaces using aryldiazonium surface chemistry. Calix[4]tetra-diazonium cations generated in situ from the corresponding tetra-anilines were electrografted on gold and carbon substrates. The well-preorganized macrocyclic structure of the calix[4]arene molecules allows the formation of densely packed monolayers. Through adequate decoration of the small rim of the Calixarenes, functional molecules can then be introduced on the immobilized Calixarene subunits, paving the way for an accurate spatial control of the chemical composition of a surface at molecular level.
Corinne Lagrost - One of the best experts on this subject based on the ideXlab platform.
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Use of Calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties
Organic and Biomolecular Chemistry, 2020Co-Authors: Ludovic Troian-gautier, Alice Mattiuzzi, Olivia Reinaud, Corinne Lagrost, Ivan JabinAbstract:Surface modification represents an active field of research that finds applications, amongst others, in the development of medical devices, sensors and biosensors, anti-biofouling materials, self-cleaning surfaces, surfaces with controlled wettability, corrosion resistance, heterogeneous catalysis and microelectronics. For some applications, surface functionalization with a nanometric-size monolayer is desired. In this review, efforts to covalently functionalize a wide array of surfaces with Calixarenes bearing diazonium groups are described. More specifically, methodologies to obtain monolayers of calix[4 or 6]arene derivatives on conductive, semi-conductive or insulating surfaces as well as on nanoparticles are presented. The main advantages of this general surface modification strategy (i.e. formation of true monolayers that can be post-functionalized, high robustness and control over the composition of the Calixarene-based coating) and its current scope of applications and future challenges are discussed.
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Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization.
Nature Communications, 2012Co-Authors: Alice Mattiuzzi, Ivan Jabin, Olivia Reinaud, Claire Mangeney, Clément Roux, Luis Santos, Jean-françois Bergamini, Philippe Hapiot, Corinne LagrostAbstract:An essential issue in the development of materials presenting an accurately functionalized surface is to achieve control of layer structuring. Whereas the very popular method based on the spontaneous adsorption of alkanethiols on metal faces stability problems, the reductive electrografting of aryldiazonium salts yielding stable interface, struggles with the control of the formation and organization of monolayers. Here we report a general strategy for patterning surfaces using aryldiazonium surface chemistry. Calix[4]tetra-diazonium cations generated in situ from the corresponding tetra-anilines were electrografted on gold and carbon substrates. The well-preorganized macrocyclic structure of the calix[4]arene molecules allows the formation of densely packed monolayers. Through adequate decoration of the small rim of the Calixarenes, functional molecules can then be introduced on the immobilized Calixarene subunits, paving the way for an accurate spatial control of the chemical composition of a surface at molecular level.
Alice Mattiuzzi - One of the best experts on this subject based on the ideXlab platform.
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Use of Calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties
Organic and Biomolecular Chemistry, 2020Co-Authors: Ludovic Troian-gautier, Alice Mattiuzzi, Olivia Reinaud, Corinne Lagrost, Ivan JabinAbstract:Surface modification represents an active field of research that finds applications, amongst others, in the development of medical devices, sensors and biosensors, anti-biofouling materials, self-cleaning surfaces, surfaces with controlled wettability, corrosion resistance, heterogeneous catalysis and microelectronics. For some applications, surface functionalization with a nanometric-size monolayer is desired. In this review, efforts to covalently functionalize a wide array of surfaces with Calixarenes bearing diazonium groups are described. More specifically, methodologies to obtain monolayers of calix[4 or 6]arene derivatives on conductive, semi-conductive or insulating surfaces as well as on nanoparticles are presented. The main advantages of this general surface modification strategy (i.e. formation of true monolayers that can be post-functionalized, high robustness and control over the composition of the Calixarene-based coating) and its current scope of applications and future challenges are discussed.
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Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization.
Nature Communications, 2012Co-Authors: Alice Mattiuzzi, Ivan Jabin, Olivia Reinaud, Claire Mangeney, Clément Roux, Luis Santos, Jean-françois Bergamini, Philippe Hapiot, Corinne LagrostAbstract:An essential issue in the development of materials presenting an accurately functionalized surface is to achieve control of layer structuring. Whereas the very popular method based on the spontaneous adsorption of alkanethiols on metal faces stability problems, the reductive electrografting of aryldiazonium salts yielding stable interface, struggles with the control of the formation and organization of monolayers. Here we report a general strategy for patterning surfaces using aryldiazonium surface chemistry. Calix[4]tetra-diazonium cations generated in situ from the corresponding tetra-anilines were electrografted on gold and carbon substrates. The well-preorganized macrocyclic structure of the calix[4]arene molecules allows the formation of densely packed monolayers. Through adequate decoration of the small rim of the Calixarenes, functional molecules can then be introduced on the immobilized Calixarene subunits, paving the way for an accurate spatial control of the chemical composition of a surface at molecular level.
Olivia Reinaud - One of the best experts on this subject based on the ideXlab platform.
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Use of Calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties
Organic and Biomolecular Chemistry, 2020Co-Authors: Ludovic Troian-gautier, Alice Mattiuzzi, Olivia Reinaud, Corinne Lagrost, Ivan JabinAbstract:Surface modification represents an active field of research that finds applications, amongst others, in the development of medical devices, sensors and biosensors, anti-biofouling materials, self-cleaning surfaces, surfaces with controlled wettability, corrosion resistance, heterogeneous catalysis and microelectronics. For some applications, surface functionalization with a nanometric-size monolayer is desired. In this review, efforts to covalently functionalize a wide array of surfaces with Calixarenes bearing diazonium groups are described. More specifically, methodologies to obtain monolayers of calix[4 or 6]arene derivatives on conductive, semi-conductive or insulating surfaces as well as on nanoparticles are presented. The main advantages of this general surface modification strategy (i.e. formation of true monolayers that can be post-functionalized, high robustness and control over the composition of the Calixarene-based coating) and its current scope of applications and future challenges are discussed.
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Electrografting of calix[4]arenediazonium salts to form versatile robust platforms for spatially controlled surface functionalization.
Nature Communications, 2012Co-Authors: Alice Mattiuzzi, Ivan Jabin, Olivia Reinaud, Claire Mangeney, Clément Roux, Luis Santos, Jean-françois Bergamini, Philippe Hapiot, Corinne LagrostAbstract:An essential issue in the development of materials presenting an accurately functionalized surface is to achieve control of layer structuring. Whereas the very popular method based on the spontaneous adsorption of alkanethiols on metal faces stability problems, the reductive electrografting of aryldiazonium salts yielding stable interface, struggles with the control of the formation and organization of monolayers. Here we report a general strategy for patterning surfaces using aryldiazonium surface chemistry. Calix[4]tetra-diazonium cations generated in situ from the corresponding tetra-anilines were electrografted on gold and carbon substrates. The well-preorganized macrocyclic structure of the calix[4]arene molecules allows the formation of densely packed monolayers. Through adequate decoration of the small rim of the Calixarenes, functional molecules can then be introduced on the immobilized Calixarene subunits, paving the way for an accurate spatial control of the chemical composition of a surface at molecular level.
Solovieva S. - One of the best experts on this subject based on the ideXlab platform.
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Thiacalix[4]arene-functionalized vesicles as phosphorescent indicators for pyridoxine detection in aqueous solution
2020Co-Authors: Mironova D., Ibragimova R., Solovieva S., König B.Abstract:© The Royal Society of Chemistry 2015. Amphiphilic tetracarboxylate derivatives of p-tert-butylthiacalix[4]arene were obtained by click reactions of the corresponding azido derivatives with acetylene dicarboxylic acid. Embedding of the amphiphilic tetraacids in DPPC vesicles was studied by DLS, AFM, turbidity techniques and by probing with merocyanine 540. The obtained DPPC-Calixarene vesicles are effective antennae for Tb(iii) ion luminescence. It allows the use of DPPC-Calixarene-Tb(iii) vesicles for the selective detection of analytes with a higher affinity for Tb(iii) due to cation removal from the Calixarenes in the DPPC bilayer. It was found that pyridoxine hydrochloride can be selectively detected at the 7 μM concentration in the presence of a 100 fold excess of different biologically important molecules, like amino acids, adenosine phosphates, sugars, amines and ammonium salts
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Investigation of hydrogen bonding in p-sulfonatocalix[4]arene and its thermal stability by vibrational spectroscopy
2020Co-Authors: Vandyukov A., Khamatgalimov A., Kleshnina S., Solovieva S.Abstract:© 2019 Elsevier B.V. The vibrational spectra of p-sulfonatocalix [4] arene were studied. The geometrical parameters, the energies, the frequencies and the intensities of the bands in the IR and Raman spectra are calculated for four conformations. The most stable conformation of the p-sulfonatocalix[4]arene is the cone due to the cooperative cyclic intramolecular hydrogen bonding system. The strength of the hydrogen bonds depends on the type of substituent on the upper rim of the Calixarene molecules. We studied the process of destruction of Calixarenes using IR spectroscopy and TGA methods. Characteristic bands for each conformation were selected. HOMO covers aromatic units with notable conjugation, and LUMO belongs to sulfonate groups
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Vibrational spectra, co-operative intramolecular hydrogen bonding and conformations of calix[4]arene and thiacalix[4]arene molecules and their para-tert-butyl derivatives
2020Co-Authors: Katsyuba S., Solovieva S., Chernova A., Vandyukova E., Shagidullin R., Konovalov A.Abstract:The IR and Raman spectra and conformations of calix[4]arene, thiacalix[4]arene and their p-rerf-butyl derivatives have been analysed within the framework of scaled quantum mechanics (SQM). It is shown that the introduction of four p-tert-Bu groups into the Calixarene molecules influences the relative energies of their conformers and the enthalpy of the cooperative intramolecular H-bonding (ΔHintra) almost negligibly. ΔHintra, evaluated from Iogansen's rule, amounts to ∼ 26-28 kcal mol-1 for the Calixarenes and ∼20-21 kcal mol -1 for the thiaCalixarenes, which essentially exceeds the enthalpies of non-cooperative H-bonds formed by related phenols. As a result of this strong bonding, bands of stretching, bending and torsion vibrations of an eight-membered cyclic system (OH ⋯)4 arise, e.g., two δ(OH)4 bands are observed in the IR spectra of the most highly symmetric C4 cone conformations of calix[4]arene and thiacalix[4]arene. The "duplication" of the number of OH infrared bands is a good new indicator of cooperativity of intramolecular H-bonding of the Calixarenes. © The Royal Society of Chemistry 2005
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Novel membrane mimetic systems based on amphiphilic oxyethylated calix[4]arene: Aggregative and liquid crystalline behavior
2020Co-Authors: Zakharova L., Gubaidullin A., Solovieva S., Kudryashova Y., Selivanova N., Voronin M., Ibragimova A., Litvinov A., Kadirov M.Abstract:Self-organization of amphiphilic Calixarenes oxyethylated at a lower rim has been investigated in water and water-organic solutions. In the range of isotropic solutions three types of structural transitions were indicated by a complex of methods. The first critical point indicated by surface tension, dynamic light scattering and atomic force microscopy methods is probably connected with the formation of " infinite" organized structures (of hundreds nanometers in size) through the open association model. This aggregative phenomenon covers the concentration range below 10-3M. In the case of aqueous Calixarene solutions these large aggregates co-exist with small micelle-like particles and undergo a rearrangement with an increase in the concentration. The second structural transition occurs beyond 10-3M. It is revealed in aqueous Calixarene solutions by surface tension, spine probe, viscosimetry and dynamic light scattering methods. Small aggregates (~10nm in diameter) are formed in this range through a closed model typical for conventional surfactants. The third transition indicated by viscosimetry and in single case by tensiometry can be connected with an elongation of aggregates. The polarization microscopy and X-ray diffraction studies reveal the anisotropic behavior with the concentration of solutions. Parameters of the existence of liquid crystalline mesophases are found to be influenced by the structure of substituents at both the upper and lower rims, as well as by the nature of solvent. © 2010 Elsevier B.V
