A FRET-based probe for fluorescence sensing of sulfide/sulfite analytes, using a novel long-wavelength water-soluble 7-hydroxycoumarin as reporter fluorophore
International audience; A FRET-based fluorescent probe for the detection of sulfide and/or sulfite in aqueous buffer, was constructed by connecting the quencher moiety nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) to a water-soluble 3-(2-benzimidazolyl)-7-hydroxycoumarin carboxylic acid through a piperazine linker. This probe exhibits good selectivity and high sensitivity for sulfite and sulfide over cysteine and other potential analytes. Furthermore, this is one of the few examples of fluorogenic coumarins whose solubility in water is maintained upon its conversion into reaction-based fluorescent probes.
On the synthesis of functionalized porphyrins and porphyrin conjugates via β-aminoporphyrins
International audience; The synthesis of functionalized porphyrins and their conjugates from meso-tetraarylporphyrins through the acylation and the oxidation of beta-aminoporphyrins was investigated. 2,3-Dioxochlorins were prepared by the oxidation of a variety of beta-aminoporphyrins and subsequently used in a condensation reaction with functionalized aromatic aldehydes and ammonium acetate to form beta-functionalized porphyrins bearing a fused imidazole ring. Under optimized experimental conditions both reactions tolerate various functional groups and afford the products in an appropriate overall yield. The mildness and usefulness of this methodology are illustrated by several examples in…
Rapid Synthesis of Unsymmetrical Sulforhodamines Through Nucleophilic Amination of a Monobrominated Sulfoxanthene Dye
A transition-metal-free method for the synthesis of N-substituted unsymmetrical sulforhodamine fluorophores from an unusual monobrominated sulfoxanthene dye and primary or secondary amines by direct SNAr-type reactions is presented. The simplicity and effectiveness of this “postamination” procedure were demonstrated through the rapid preparation of a library of multifunctional red-emitting rhodamine analogues. Some of these analogues are equipped with a reactive handle and retain the two water-solubilizing sulfonic acid moieties of the starting halogenated derivative; this makes them ideal candidates for biolabeling applications. The potential utility of this expeditious strategy to finely …
Kondrat'eva ligation: Diels-Alder-based irreversible reaction for bioconjugation.
International audience; Diversification of existing chemoselective ligations is required to efficiently access complex and well-defined biomolecular assemblies with unique and valuable properties. The development and bioconjugation applications of a novel Diels-Alder-based irreversible site-specific ligation are reported. The strategy is based on a Kondrat'eva cycloaddition between bioinert and readily functionalizable 5-alkoxyoxazoles and maleimides that readily react together under mild and easily tunable reaction conditions to afford a fully stable pyridine scaffold. The potential of this novel bioconjugation is demonstrated through the preparation of fluorescent conjugates of biomolecul…
A novel bio-orthogonal cross-linker for improved protein/protein interaction analysis
International audience; The variety of protein cross-linkers developed in recent years illustrates the current requirement for efficient reagents optimized for mass spectrometry (MS) analysis. To date, the most widely used strategy relies on commercial cross-linkers that bear an isotopically labeled tag and N-hydroxysuccinimid-ester (NHS-ester) moieties. Moreover, an enrichment step using liquid chromatography is usually performed after enzymatic digestion of the cross-linked proteins. Unfortunately, this approach suffers from several limitations. First, it requires large amounts of proteins. Second, NHS-ester cross-linkers are poorly efficient because of their fast hydrolysis in water. Fin…
The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation
Recent advances in the use of radiometals for both imaging and therapy has spurred on the development of an original chemistry that endows radionuclide-chelating molecular cages with ever sharper physicochemical properties. Macrocyclic polyamines (MPAs) such as cyclen and DOTA are among the most frequently encountered cages for the design of new radiotracers, owing to their versatile chemistry that makes them customizable molecular tools. The idea of using MPAs for alternative purposes has recently emerged, with an eye towards benefiting from their unique topology, versatility, symmetry and water-solubility. This review summarizes strategies that have been recently implemented in which MPAs…
A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells
We have designed an A–π–D–π–A small-molecule triad consisting of a bacteriochlorin (BC) donor central core linked with two diketopyrrolopyrrole (DPP) acceptors via ethynyl bridges (BC-DPP-1). BC-DPP-1 has a narrow optical bandgap of 1.38 eV with highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of −4.93 eV and −3.40 eV, respectively, and it was used as an electron donor along with [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an acceptor for solution-processed small-molecule organic solar cells. After optimizing the weight ratio between BC-DPP-1 and PC71BM and pyridine as a solvent additive and subsequent solvent vapor annealing using THF, an …
Fluorogenic Enzyme-Triggered Domino Reactions Producing Quinoxalin-2(1H)-one-based Heterocycles
International audience; A simple and effective biocompatible domino reaction triggered by a model protease and leading to formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including versatility and ability to provide outstanding fluorescence "OFF-ON" responses were revealed by this work. They open the way for practical applications of this novel type of "covalent-assembly" based fluorescent probes in the fields of sensing and bioimaging. Among the myriad of synthetic transformations and catalysts currently available for concise and efficient synthesis of organic molecules, bioinspired approaches based on the use of enzymes often int…
Straightforward synthesis of bioconjugatable azo dyes. Part 2: Black Hole Quencher-2 (BHQ-2) and BlackBerry Quencher 650 (BBQ-650) scaffolds
Abstract A further extension of the efficient synthetic methodology described in Part 1, to the aromatic bis-diazo scaffold of Black Hole Quencher-2 dye is presented. Bioconjugatable derivatives bearing either azido, terminal alkyne, or maleimide reactive group were easily obtained as well as the free-phenol form of BlackBerry® Quencher 650 (BBQ-650®) initially developed by Berry & Associates, Inc. Company. The efficient conjugation ability of azido- and maleimide-quenchers was demonstrated through the facile preparation of the first water-soluble and formylated BHQ-2 dyes and a FRET-based probe suitable for the in vitro/in cellulo detection of a cancer-associated protease namely urokinase-…
New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds
Abstract The synthesis and photophysical properties of novel water-soluble phenol-based fluorophores derived from 3-benzothiazolyl-7-hydroxycoumarin and emitting in the range 485–631 nm are described. Further conversion into thiol-sensitive fluorogenic probes through the chemical modification of their hydroxyl group was next investigated. Depending on the type of thiol-reactive quenching moiety used (2,4-dinitrobenzenesulfonyl ester, 2,4-dinitrophenyl ether or benzoquinone-type Michael acceptors) and the water-solubilizing group(s) pre-introduced into the coumarin core, dramatic differences in the thiol-induced fluorescence activation of these pro-fluorophores under physiological conditions…
Site-specific near-infrared fluorescent labelling of proteins on cysteine residues with meso -chloro-substituted heptamethine cyanine dyes
International audience; Near-infrared (NIR) fluorescence imaging is a promising new medical imaging modality. Associated with a targeting molecule, NIR fluorophores can accumulate selectively in tissues of interest and become valuable tools for the diagnosis and therapy of various pathologies. To facilitate the design of targeted NIR imaging agents, it is important to identify simple and affordable fluorescent probes, allowing rapid labelling of biovectors such as proteins, ideally in a site-specific manner. Here, we demonstrate that heptamethine cyanine based fluorophores, such as IR-783, that contain a chloro-cyclohexyl moiety within their polymethine chain can react selectively, at neutr…
Straightforward synthesis of bioconjugatable azo dyes. Part 1: Black Hole Quencher-1 (BHQ-1) scaffold
Abstract Azo dyes are currently used to quench the fluorescence of energy donors in bioassays through Forster resonance energy transfer (FRET) phenomenon. Common examples of such dark quenchers are DABCYL and the three members of Black Hole Quencher® (BHQ) family. Yet, only carboxylic acid and phosphoramidite derivatives of such azo dyes are presently commercially available. This Letter presents a straightforward synthesis method to novel bioconjugatable quenchers derived from BHQ-1 scaffold and equipped with a reactive group being either azido, terminal alkyne, or maleimide. The potential utility of the ‘clickable’ azido and thiol-reactive derivatives was notably demonstrated through the p…
“AND” luminescent “reactive” molecular logic gates: a gateway to multi-analyte bioimaging and biosensing
This review outlines examples that illustrate a recent and highly innovative concept in the field of (bio)molecular sensing, namely the simultaneous multi-analyte detection using "reactive" luminescent probes that are able to produce an optical signal only in response to multiple (bio)chemical inputs and through covalent chemical reactions with target (bio)analytes. Unlike conventional "AND" molecular logic gates based on supramolecular photochemical mechanisms, these unusual "smart" optical (bio)probes are suitable tools to track the rise and fall of a wider range of biologically relevant analytes, in complex media and with higher selectivity. The potential utility of this concept for in v…
A Novel Enzyme-Triggered Domino Reaction Producing Fluorescent Quinoxalin-2(1H)-One-Based Heterocycles
A simple and effective biocompatible domino reaction triggered by a model protease and leading to formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including versatility and ability to provide outstanding fluorescence "OFF-ON" responses were revealed by this work. They open the way for practical applications of this novel type of "covalent-assembly" based fluorescent probes in the fields of sensing and bioimaging.; A simple and effective biocompatible domino reaction triggered by a model protease and leading to formation of strongly fluorescent quinoxalin-2(1H)-one N-heterocycles is described. Some positive attributes including vers…
Synthesis, stability and spectral behavior of fluorogenic sulfone-pyronin and sulfone-rosamine dyes
International audience; The first synthesis of sulfone-pyronin and sulfone-rosamine dyes bearing optically tunable primary amino groups (acting as fluorogenic centers) is presented. Sulfone analogs of xanthene-based fluorophores have recently been highlighted as a new class of near-infrared (NIR) fluorescent dyes (Liu et al. ACS Appl Mater Interfaces 2016; 8(35):22953-62), and the availability of fluorogenic derivatives is essential for the rapid construction of “turn-on” reactive probes for chemoselective bioimaging. However, these fluorescent anilines have been found to be unstable in aqueous physiological conditions due to the marked electrophilicity of their meso-position and hence its …
Thiocarbamate-Linked Polysulfonate–Peptide Conjugates As Selective Hepatocyte Growth Factor Receptor Binders
The capacity of many proteins to interact with natural or synthetic polyanions has been exploited for modulating their biological action. However, the polydispersity of these macromolecular polyanions as well as their poor specificity is a severe limitation to their use as drugs. An emerging trend in this field is the synthesis of homogeneous and well-defined polyanion–peptide conjugates, which act as bivalent ligands, with the peptide part bringing the selectivity of the scaffold. Alternately, this strategy can be used for improving the binding of short peptides to polyanion-binding protein targets. This work describes the design and first synthesis of homogeneous polysulfonate–peptide con…
Azo-Sulforhodamine Dyes: A Novel Class of Broad Spectrum Dark Quenchers
A rapid access to a novel class of water-soluble dark quencher dyes was achieved using an azo-coupling reaction between a fluorescent primary arylamine derived from a sulforhodamine 101 scaffold and a tertiary aniline equipped with different bioconjugatable groups. The thus obtained nonfluorescent azo-sulforhodamine hybrids display a broad quenching range spanning the visible to NIR regions. This was demonstrated through the preparation and enzymatic activation of FRET-based fluorogenic substrates of urokinase.
The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation
International audience; Recent advances in the use of radiometals for both imaging and therapy has spurred on the development of an original chemistry that endows radionuclide-chelating molecular cages with ever sharper physicochemical properties. Macrocyclic polyamines (MPAs) such as cyclen and DOTA are among the most frequently encountered cages for the design of new radiotracers, owing to their versatile chemistry that makes them customizable molecular tools. The idea of using MPAs for alternative purposes has recently emerged, with an eye towards benefiting from their unique topology, versatility, symmetry and water-solubility. This review summarizes strategies that have been recently i…
Design, Synthesis and Evaluation of Enzyme-Responsive Fluorogenic Probes Based on Pyridine-Flanked Diketopyrrolopyrrole Dyes
The ever-growing demand for fluorogenic dyes usable in the rapid construction of analyte-responsive fluorescent probes, has recently contributed to a revival of interest in the chemistry of diketopyrrolopyrrole (DPP) pigments. In this context, we have explored the potential of symmetrical and unsymmetrical DPP derivatives bearing two or one 4-pyridyl substituents acting as optically tunable group(s). The unique fluorogenic behavior of these molecules, closely linked to N-substitution/charge state of their pyridine unit (i.e., neutral pyridine or cationic pyridinium), has been used to design DPP-based fluorescent probes for detection of hypoxia-related redox enzymes and penicillin G acylase …
Highly Fluorescent and Water-Soluble Diketopyrrolopyrrole Dyes for Bioconjugation
International audience; The preparation of highly water-soluble and strongly fluorescent diketopyrrolopyrrole (DPP) dyes using an unusual taurine-like sulfonated linker has been achieved. Exchanging a phenyl for a thienyl substituent shifts the emission wavelength to near λ=600 nm. The free carboxylic acid group present in these new derivatives was readily activated and the dyes were subsequently covalently linked to a model protein (bovine serum albumin; BSA). The bioconjugates were characterized by electronic absorption, fluorescence spectroscopy and MALDI-TOF mass spectrometry, thus enabling precise determination of the labeling density (ratio DPP/BSA about 3 to 8). Outstanding values of…
Front Cover: The Scope of Application of Macrocyclic Polyamines Beyond Metal Chelation (Eur. J. Org. Chem. 36/2019)
International audience
Oxidative C-N fusion of pyridinyl-substituted porphyrins.
International audience; The mild (electro) chemical oxidation of pyridin-2-ylthio-meso substituted Ni(II) porphyrins affords C-N fused cationic and dicationic pyridinium-based derivatives. These porphyrins are fully characterized and the molecular structure of one of them was confirmed by X-ray crystallography. A mechanism for the intramolecular oxidative C-N coupling is proposed based on theoretical calculations and cyclic voltammetry analyses.
Functionalization of theranostic AGuIX® nanoparticles for PET/MRI/optical imaging
International audience; A novel trifunctional imaging probe containing a chelator of radiometal for PET, a NIR heptamethine cyanine dye, and a bioconjugatable handle, has been grafted onto AGuIX® nanoparticles via a Michael addition reaction. The resulting functionalized nanoparticles have been fully characterized, radiolabelled with 64Cu, and evaluated in a mice TSA tumor model using multimodal (PET/MRI/optical) imaging.
Rational Design of Latent Fluorophores from Water-Soluble Hydroxyphenyltriazine Dyes Suitable for Lipase Sensing
The phenol residue of water‐soluble 2‐(2′‐hydroxy‐5′‐dimethylaminobenzyl)‐4,6‐dimethylamino‐1,3,5‐triazine is masked by an enzyme‐labile protecting group constructed with a self‐immolative para‐hydroxybenzyl alcohol. The fluorescence of the dyes is restored with lipases under physiological conditions without aggregation or precipitation of the fluorescent dyes. Derivatives of 2‐(2′‐hydroxy‐5′‐dimethylaminobenzyl)‐4,6‐dimethylamino‐1,3,5‐triazine were synthesized by an original multistep protocol that afforded, after quaternization of the N,N‐dimethylaminobenzyl moiety, water‐soluble fluorescent dyes. These fluorophores exhibited excited‐state intramolecular proton transfer and large Stokes …
A Synthetic Route to 3-(Heteroaryl)-7-hydroxycoumarins Designed for Biosensing Applications
A straightforward method to synthesize 3-(2-benzimidazolyl)-7-hydroxycoumarins, based on the condensation reaction of 7-acetoxy-3-formylcoumarin with various C- and/or N-substituted ortho-phenylenediamine derivatives is presented. This unusual approach proved particularly effective for introducing different hydrophilic groups (carboxylic or sulfonic acids or trimethylalkylammonium moieties) onto the heteroaryl scaffold, leading to cyan-green emitting coumarins that were both water-soluble and strongly fluorescent under physiological conditions. The further extension of this condensation reaction to bis(2-aminophenyl)diselenide enabled the first synthesis of 3-(2-benzoselenazolyl)-7-hydroxyc…
Synthetic routes to novel fluorogenic pyronins and silicon analogs with far-red spectral properties and enhanced aqueous stability
Fluorogenic detection of reactive (bio)analytes is often achieved with "smart" probes, whose activation mechanism causes the release of aniline-based fluorophores. Indeed, the protection-deprotection of their primary amino is the simplest way to induce dramatic and valuable changes in spectral features of the fluorogenic reporter. In this context, and due to their small size and intrinsic hydrophilicity, we focused on pyronin dyes and related heteroatom analogs (i.e., formal derivatives of 3-imino-3H-xanthen-6-amine and its silicon analog) for their use as optically tunable aniline-based fluorophores. To overcome some severe limitations associated with the use of such fluorogenic scaffolds …
Rationalisation of the Optical Signatures of nor-Dihydroxanthene-Hemicyanine Fused Near-Infrared Fluorophores By First Principle Tools
Using a computational approach combining the Time-Dependent Density Functional Theory (TD-DFT) and the second-order Coupled Cluster (CC2) approaches, we investigate the spectral properties of a large panel of nor-dihydroxanthene (DHX)-hemicyanine fused dyes. First we compare the theoretical and experimental 0-0 energies for a set of 14 known synthetic compounds and show that a remarkable agreement between theory and experiment is obtained when a suitable environmental model is selected. In addition, we obtain vibrationally-resolved spectra for several compounds and theory also accurately reproduces the experimental band shapes. We show that the electronic transitions in nor-DHX-based fluoro…
Straightforward access to water-soluble unsymmetrical sulfoxanthene dyes: application to the preparation of far-red fluorescent dyes with large stokes' shifts.
An efficient synthesis of water-soluble unsymmetrical sulforhodamine/sulforhodol fluorophores containing a single julolidine fragment is presented. Owing to their valuable spectral properties in aqueous buffers, these dyes, especially those bearing a free aniline or phenol moiety, are valuable components of fluorogenic probes for a variety of biosensing applications. A further extension of this synthetic methodology to unusual phenols, namely 7-N,N-dialkylamino-4-hydroxy coumarins has enabled us to provide a new family water-soluble dyes of large Stokes’ shift with far-red spectral features.
Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation
Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine. The X-ray crystallographic structure of the unstable 2-aminotetraphenylporphyrin was solved. Protonation of this latter compound leads to the stable diiminium porphyrin salt.
Dual enzyme-responsive "turn-on" fluorescence sensing systems based on in situ formation of 7-hydroxy-2-iminocoumarin scaffolds.
A new strategy for the simultaneous fluorogenic detection of two distinct enzyme activities namely hydrolase (amidase or esterase) and reductase is described. This innovative biosensing method is based on the powerful "covalent-assembly" principle that involves in situ synthesis of a fluorophore from a non-fluorescent caged precursor and through domino reactions triggered by the two analytes of interest. To establish this approach, penicillin G acylase (PGA) (or pig liver esterase (PLE)) and nitroreductase (NTR) were chosen as model enzymes, and original bis-O-protected 2,4-dihydroxycinnamonitrile derivatives acting as dual-reactive probes readily convertible to highly fluorescent 7-hydroxy…
Near-infrared emissive bacteriochlorin-diketopyrrolopyrrole triads: Synthesis and photophysical properties
International audience; The synthesis of unprecedented energy transfer triads containing a near-infrared (NIR) emissive bacteriochlorin subunit and two diketopyrrolopyrrole (DPP) moieties linked to each other via ethynyl or zero-carbon spacers is presented. Their optical and fluorescence properties were determined in CHCl3 and toluene. These photophysical measurements highlight the ability of DPP scaffold to act as an effective energy donor, which once excited in the range 450-550 nm resulting nearly exclusively NIR emission of hydroporphyrin (ETE > 96%). Since DPP dyes are valuable structurally tunable fluorophores that may be used in the construction of high-performance multicomponent pho…
A novel water-soluble BODIPY dye as red fluorescent probe for imaging hypoxic status of human cancer cells
The development of effective methods for real-time monitoring of nitroreductase (NTR) activity is of great significance for medical diagnosis and cancer research. Here, we present a novel water-soluble BODIPY-based chemodosimeter (NBB) for imaging the hypoxic status of human non-small-cell lung cancer A549 cells. We assume that ‘on–off’ response of NBB is activated by the NTRmediated reductive release of meso-phenol BODIPY dye resulting in unusual fluorescence.
Reappraising Schmidpeter's bis(iminophosphoranyl)phosphides: coordination to transition metals and bonding analysis
The synthesis and characterization of a range of bis(iminophosphoranyl)phosphide (BIPP) group 4 and coinage metals complexes is reported. BIPP ligands bind group 4 metals in a pseudo fac-fashion, and the central phosphorus atom enables the formation of d0–d10 heterobimetallic complexes. Various DFT computational tools (including AIM, ELF and NCI) show that the phosphorus–metal interaction is either electrostatic (Ti) or dative (Au, Cu). A bridged homobimetallic Cu–Cu complex was also prepared and its spectroscopic properties were investigated. The theoretical analysis of the P–P bond in BIPP complexes reveals that (i) BIPP are closely related to ambiphilic triphosphenium (TP) cations; (ii) …
In situ formation of pyronin dyes for fluorescence protease sensing
International audience; We report a reaction-based strategy for the fluorogenic detection of protease activity. Based on the "covalent-assembly" probe design principle recently put forward by the Yang group for detection of Sarin related threats (J. Am. Chem. Soc., 2014, 136, 6594-6597), we have designed two unusual nonfluorescent caged precursors (mixed bis-aryl ethers) which are readily converted into a fluorescent unsymmetrical pyronin dye through a domino cyclisation-aromatisation reaction triggered by penicillin G acylase (PGA) or leucine aminopeptidase (LAP). Fluorescence-based in vitro assays and HPLCfluorescence/- MS analyses support the claimed activation mechanism whose the furthe…
CCDC 1557313: Experimental Crystal Structure Determination
Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F
CCDC 1985146: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985142: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985138: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985136: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1952439: Experimental Crystal Structure Determination
Related Article: Asmae Bousfiha, Abdou K. D. Dimé, Amelle Mankou-Makaya, Julie Echaubard, Mathieu Berthelot, Hélène Cattey, Anthony Romieu, Julien Roger, Charles H. Devillers|2020|Chem.Commun.|56|884|doi:10.1039/C9CC07351E
CCDC 1985140: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985143: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1557314: Experimental Crystal Structure Determination
Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F
CCDC 1985135: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985137: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985139: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1910052: Experimental Crystal Structure Determination
Related Article: Flavien Ponsot, Léo Bucher, Nicolas Desbois, Yoann Rousselin, Pritam Mondal, Charles H. Devillers, Anthony Romieu, Claude P. Gros, Rahul Singhal, Ganesh D. Sharma|2019|J.Mater.Chem.C|7|9655|doi:10.1039/C9TC02724F
CCDC 1985134: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1813003: Experimental Crystal Structure Determination
Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F
CCDC 1952440: Experimental Crystal Structure Determination
Related Article: Asmae Bousfiha, Abdou K. D. Dimé, Amelle Mankou-Makaya, Julie Echaubard, Mathieu Berthelot, Hélène Cattey, Anthony Romieu, Julien Roger, Charles H. Devillers|2020|Chem.Commun.|56|884|doi:10.1039/C9CC07351E
CCDC 1985141: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985144: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H
CCDC 1985145: Experimental Crystal Structure Determination
Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H