Sébastien Balieu

Université de Rouen | UR · Département de Chimie

Commercial oleogelators rich in monoglycerides (MGs) are complex mixtures of acylglycerides with variable gelling properties, depending on the oil used and their concentration. In this study we developed a chemometric approach to identify the key parameters involved in gelling process. Analytical parameters have been defined, using GC and NMR analy...

We developed a new hybrid material resulting from an innovative supramolecular tripartite association between an ionic liquid covalently immobilized on primary β-cyclodextrins rim and an anionic water-soluble polymer. Two hydrophilic ternary complexes based on native and permethylated β-cyclodextrins substituted with an ionic liquid and immobilized...

We developed a new hybrid material resulting from an innovative supramolecular tripartite association between an ionic liquid covalently immobilized on primary β-cyclodextrins rim and an anionic water-soluble polymer. Two hydrophilic ternary complexes based on native and permethylated β-cyclodextrins substituted with an ionic liquid and immobilized...

In the search for improvement in the properties of gadolinium-based contrast agents, cyclodextrins (CDs) are interesting hydrophilic scaffolds with high molecular weight. The impact of the hydrophilicity of these systems on the MRI efficacy has been studied using five β-CDs substituted with DOTA or TTHA ligands which, respectively, allow for one (q...

A Molecularly Imprinted Polymer containing a porphyrin unit was developed as a biomimetic heteregenous catalyst for oxidation of sulfur derivatives. Its catalytic efficiency under mild conditions and its easy recovery...

A new synthetic route towards a bifunctional ionic liquid-bridged organotrichlorotin derivative has been developed. This newly isolated compound acts as an efficient, solvent-free catalyst in the ROP of ε-caprolactone to provide polymers with controlled molecular weights and narrow dispersity (Đ < 1.2). Owing to its easy removal from the medium, IC...

This expansive and practical textbook contains organic chemistry experiments for teaching in the laboratory at the undergraduate level covering a range of functional group transformations and key organic reactions.The editorial team have collected contributions from around the world and standardized them for publication. Each experiment will explor...

The aim of this review is to provide an update on the current use of cyclodextrins against organophosphorus compound intoxications. Organophosphorus pesticides and nerve agents play a determinant role in the inhibition of cholinesterases. The cyclic structure of cyclodextrins and their toroidal shape are perfectly suitable to design new chemical sc...

The iterative homologation of boronic esters using chiral lithiated benzoate esters and chloromethyllithium has been applied to the highly efficient syntheses of two natural products, (+)-kalkitoxin and (+)-hydroxyphthioceranic acid. The chiral lithiated benzoate esters (>99% ee) were generated from the corresponding stannanes, which themselves wer...

Molecular 'assembly lines', in which organic molecules undergo iterative processes such as chain elongation and functional group manipulation, are found in many natural systems, including polyketide biosynthesis. Here we report the creation of such an assembly line using the iterative, reagent-controlled homologation of a boronic ester. This proces...

Polypropyleneimines (PPIs) functionalized by glycerol-based entities are prepared and characterized by diffusion-ordered spectroscopy NMR. Showing low cytotoxicity against MRC5 fibroblasts, their encapsulation capacities of gadolinium complexes was evaluated. T(1) measurements were performed to determine the relaxivity of the encapsulated gadopente...

Review: preparation of open-chain, pyranose and furanose derivatives; 26 refs.

A straightforward formation of six- and eight-membered rings via the radical cyclization of specifically designed ynamides is reported. This strategy provides a protoberberine analog in only three steps by a radical cyclization cascade.

Despite the fact that L-sorbose has been widely used for the synthesis of vitamin C at an industrial level, its use in organic synthesis remains rare. However, a survey of the chemical literature shows that this unusual sugar can be transformed into interesting derivatives. L-Sorbose, an interesting natural sugar, shows structural similarity to wel...

First to fifth generations of poly(propyleneimines) (PPIs) were reacted with glycerol carbonate yielding a new family of glycerol-decorated PPIs (GD-PPI). Owing to the presence of glyceryl units surrounding the PPI core, the high generation GD-PPI-5 can be successfully immobilized in a glycerol phase, thus offering a convenient route for possible u...

We report the condensation of 3-chloromethyl-benzoyl chloride with two atropisomers ααββ and αβαβ of meso-5,10,15,20-tetrakis-(2-amino)phenylporphyrin (TAPP), followed by the reaction of the anion of either cyano-acetic acid ethyl ester or (4-nitro-phenyl)-acetic acid ethyl ester to prepare various pre-organized strapped porphyrins. These two reage...

A general method to synthesize various alphabeta alphabeta bis-strapped porphyrins, with a different functionalization on each side of the macrocycle, is described. The resulting new chelates may find applications as analogues of heme protein active sites, bifunctional chelates, or specific bis-chelating molecules with potential medical utility.

A comparative study of bismuth complexation by various porphyrins which differ according to the structural scaffold – either picket(s) or strap(s) – that deliver the carboxylic acid groups close to the metal, has been performed. Unlike strapped porphyrins, and although more flexible, the picket ligands do not lead to more stable bismuth complexes.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

As 213Bi, a spontaneous alpha-emitting radioisotope, and 10B, a neutron-activated source of alpha particles, have been found to be potential tools in the treatment of cancer patients, a novel bismuth porphyrin, bearing both boron atoms and a strap with a hanging carboxylic group, was synthesized.

The coordination chemistry of porphyrins towards the complexation of bimuth(III) has been investigated. Although the insertion of bismuth is tedious in porphyrins such as octa-ethyl porphyrin (OEP) or tetra-tolyl porphyrin (TTP), we have demonstrated that simple modifications of the ligand, like the grafting of arms bearing either ester groups or a...

The condensation of 3-chloromethylbenzoyl chloride with three atropisomers of meso-5,10,15,20-tetrakis(2-aminophenyl)porphyrin (TAPP) is reported, followed by the reaction of the anion of diethyl malonate to prepare various strapped porphyrins. According to two different geometries of the straps, the resulting preorganization of the hanging ethoxyc...

Synthetic methodologies aiming at the creation of new phosphorus-centered functional groups are reported, as well as applications to the field of nucleotide chemistry. Thus, difluorophosphonothioate-based, ionic reagents 3b and 3d are shown to allow the stereocontrolled and efficient synthesis of phosphonodifluoromethyl analogues of nucleoside-3′-p...

Efforts to develop synthetic methodologies allowing the preparation of α,α– difluorophosphonothioates, α,α–difluorophosphonodithioates, α,α–difluorophosphono- trithioates, and α,α–difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphat...

Efforts to develop synthetic methodologies allowing the preparation of alpha,alpha- difluorophosphonothioates, alpha,alpha-difluorophosphonodithioates, alpha,alpha-difluorophosphono- trithioates, and alpha,alpha-difluorophosphinates are reviewed in the light of applications in the field of modified oligonucleotides and cyclitol phosphates. Two succ...

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Efforts to stereoselectively install difluorophosphonyl, difluorophosphonothioyl and difluorophosphinyl groups in place of the phosphate linking positions 3′ and 5′ of two furanoses are reviewed. Two equally efficient approaches have been worked out based on either the ionic addition of difluorophosphonothioate reagents 17 or 33 onto a ketone, or o...