0000000000000793
AUTHOR
Rita Meunier-prest
Tuning of interfacial charge transport in polyporphine/phthalocyanine heterojunctions by molecular geometry control for an efficient gas sensor
Abstract Owing to high interfacial conductivity, organic heterostructures hold great promises to augment the electrical performances of electronic devices. In this endeavor, the present work reports fabrication of novel polyporphine/phthalocyanine heterostructures and investigates the modulation of charge transport induced by structural change of polyporphine and its implication on ammonia sensing properties. Polyporphines materials are electrosynthesized by oxidation of zinc(II) porphine monomer that corresponds to the fully unsubstituted porphyrin. At less-positive anodic potential, low conducting meso,meso-singly-linked type-1 polymer (pZnP-1) is formed in which a monomer unit stays orth…
Modulation of the organic heterojunction behavior, from electrografting to enhanced sensing properties
International audience; The energy barrier of an organic heterojunction built on ITO electrodes and made from a low conductive sublayer (Cu(F16Pc)) covered by a highly conductive semiconductor (LuPc2) is modulated by electrografting of organic layers before depositing the sublayer. Impedance spectroscopy clearly demonstrates the increase of the energy barrier at the ITO – sublayer interface. Additionally, the electrografting is a versatile and promising method for the tuning of heterojunctions. The I(V) characteristics of the heterojunctions are highly modified by the electrografting. The same electromodifications of electrodes carried out on LuPc2 resistors lead to a modification of their …
Direct measurement of the melting temperature of supported DNA by electrochemical method
The development of biosensors based on DNA hybridization requires a more precise knowledge of the thermodynamics of the hybridization at a solid interface. In particular, the selectivity of hybridization can be affected by a lot of parameters such as the single-strand (ss)DNA density, the pH, the ionic strength or the temperature. The melting temperature, T(m), is in part a function of the ionic strength and of the temperature and therefore provides a useful variable in the control of the selectivity and sensitivity of a DNA chip. The electrochemical technique has been used to determine the T(m) values when the probe is tethered by a DNA self-assembled monolayer (SAM). We have built a speci…
Organic Heterojunction Devices Based on Phthalocyanines: A New Approach to Gas Chemosensing.
Organic heterostructures have emerged as highly promising transducers to realize high performance gas sensors. The key reason for such a huge interest in these devices is the associated organic heterojunction effect in which opposite free charges are accumulated at the interface making it highly conducting, which can be exploited in producing highly sensitive and faster response kinetics gas sensors. Metal phthalocyanines (MPc) have been extensively studied to fabricate organic heterostructures because of the large possibilities of structural engineering which are correlated with their bulk thin film properties. Accordingly, in this review, we have performed a comprehensive literature surve…
Electrochemical and Spectroelectrochemical Behavior of a Tetracyanotriphenodioxazine in Solution and Thin-Films
International audience; We report the electrochemical behavior of a tetracyano triphenodioxazine bearing two triisopropylsilylethynyl moieties (TiPS‐TPDO‐tetraCN) during its reduction studied either in solution or after vacuum evaporation deposition on indium tin oxide (ITO) support. While in dichloromethane, it typically proceeds in two successive monoelectronic reactions, in acetonitrile, the mechanism appears more complex. Fine analysis of the spectroelectrochemical results combined with simulation of the voltammograms with various amount of water suggest the involvement of water and of a restructured dianion in the electrochemical process. In the solid‐state, the formation of the diprot…
Photon assisted-inversion of majority charge carriers in molecular semiconductor-based organic heterojunctions
International audience; Ambipolar molecular materials hold great promises as a building block of next generation highly efficient, less complex and low cost electronics devices. In this endeavor, the present work reports the fabrication of organic heterojunction devices based on halogenated copper Phthalocyanines (CuPc) and lutetium bisphthalocyanine (LuPc2) bilayer, investigates their structural and electrical properties and probes the ambipolar behavior by ammonia sensing. Microstructural analysis of the heterostructure thin films revealed compact and semicrystalline organization, depending on the number of halogen substituents in CuPc. The heterojunction devices reveal a non-linear I(V) …
Tuning Of Organic Heterojunction Conductivity By The Substituents' Electronic Effects In Phthalocyanines For Ambipolar Gas Sensors
Abstract Exploiting organic heterojunction effects in electrical devices are an important strategy to improve the electrical conductivity, which can be utilized into improving the conductometric gas sensors performances. In this endeavor, the present article reports fabrication of organic heterostructures in a bilayer device configuration incorporating octa-substituted nickel phthalocyanines (NiPc) and radical lutetium bis-phthalocyanine (LuPc2) and investigates their sensing properties towards NH3 vapor. NiPc having hexyl sulfanyl, hexyl sulfonyl and p-carboxyphenoxy moieties are synthesized, which electronic effects are electron donating, accepting and moderate accepting, respectively, al…
Ferrocenyl glycopeptides as electrochemical probes to detect autoantibodies in multiple sclerosis patients' será
Abstract Glycopeptide analogues of CSF114(Glc), modified at N-terminus with new ferrocenyl carboxylic acid and a new ferrocenyl-thiphosphino amino acid, were used to implement a new electrochemical biosensor for autoantibody detection in multiple sclerosis. The ferrocenyl moiety of these "electrochemical probes" did not affect autoantibody recognition both in SP-ELISA and in inhibition experiments. By electrochemical monitoring the interactions of the modified peptides Fc-CSF114(Glc) and 4-FcPhP(S)Abu-CSF114(Glc) with the autoantibodies, we demonstrated that autoantibodies could be detected with a sensitivity comparable to ELISA method. The new electrochemical probes can be proposed to char…
Conducting Polymers for Ammonia Sensing: Electrodeposition, Hybrid Materials and Heterojunctions
International audience; Polyaniline (PANI) with electrodonating and electrowithdrawing substituents were electrodeposited and studied as sensing materials in resistors and heterojunctions. Whereas the dimethoxyaniline leads to a highly conductive material, the tetrafluoroaniline leads to a poor conducting polymer. However, this latter was used in heterojunctions, associated with a highly conductive material, the lutetium bisphthalocyanine LuPc2. Elsewhere, hybrid materials combining polypyrrole (PPy) with ionic macrocycles as counterions were also electrosynthesized and used as sensing material in resistors, for the detection of ammonia. They exhibit a higher sensitivity compared to PPy pre…
Electrochemistry of methylene blue at an alkanethiol modified electrode
International audience; Gold surfaces were derivatized with decanethiol. The electrochemistry of methylene blue at these modified electrodes was investigated in function of the gold cleaning process and compared with the results obtained at a bare gold electrode. Cyclic voltammetry at low methylene blue concentrations (c(MB) <= 16 mu M) yielded surface behavior data. The properties of the film vary with the electrode pretreatment. Without electrochemical cleaning step, the standard potential at a gold electrode modified with 1-decanethiol is nearly the same as on a bare gold electrode. On the other hand, when the electrode is electrochemically cleaned before adsorption of the alkanethiols, …
Mass Transport in Nanoporous Gold and Correlation with Surface Pores for EC 1 Mechanism: Case of Ascorbic Acid
International audience; Entry for the Table of Contents Playing with the pores: Surface pores size in nanoporous gold modulates the electrode reactions pathways of ascorbic acid. The reaction is largely driven by diffusion when pores are smaller (nanometer). On the contrary, adsorption holds the key role when pores are bigger (micrometer), allowing permeation of molecules in the film volume.
Molecular Engineering of Porphyrin‐Tapes/Phthalocyanine Heterojunctions for a Highly Sensitive Ammonia Sensor
International audience; Modulating the interfacial charge alignments by molecular engineering in an organic heterojunction device is a smart strategy to improve its conductivity, which can be exploited in high performance gas sensors development. Herein, the fabrication of new organic heterojunction devices based on porphyrin tapes and phthalocyanines and their potentiality in ammonia sensing at different relative humidity (rh) are investigated. The devices are built using dry approach relying on oxidative chemical vapor deposition for simultaneous synthesis, doping and deposition of the porphyrin tape layer and physical vapor deposition of phthalocyanine layer. The association of the porph…
Potential-assisted deposition of mixed alkanethiol self-assembled monolayers
Abstract Preparation of self-assembled monolayers (SAMs) usually involves passive incubation. The recently developed potential-assisted deposition is indeed more selective as well as 100-fold faster than passive adsorption, thereby enhancing the reproducibility of the monolayer deposition. This article aims to identify the electrodeposition conditions necessary to prepare mixed alkanethiol SAMs on gold surface. Parameters such as concentrations in solution, electrode polarization and deposition time were examined for two chain lengths, C 3 (mercaptopropionic acid, MPA) and C 18 (octadecanethiol, ODT). The kinetics and composition of the SAMs were systematically characterized by reductive st…
Proton coupled electron transfer of ubiquinone Q2 incorporated in a self-assembled monolayer.
We present a complete study of the reduction of ubiquinone Q(2) (UQ(2)) in simpler aqueous medium, over a pH range of 2.5 to 12.5. The short isoprenic chain ubiquinones (UQ(2)) were incorporated in a self-assembled monolayer. Under these conditions, the global 2e(-) electrochemical reaction can be described on the basis of a nine-member square scheme. The thermodynamic constants of the system were determined. The global 2e(-) process is controlled by the uptake of the second electron. The elementary electrochemical rate constants obtained by fitting of the experimental rate constant were k(s4) = 1.5 s(-1) for QH˙(+)(2)↔ QH(2), k(s5) = 1.5 s(-1) for QH˙↔ QH(-) and k(s6) = 1 s(-1) for Q˙(-)↔ …
Alkylthio-tetrasubstituted μ-Nitrido Diiron Phthalocyanines: Spectroelectrochemistry, Electrical Properties, and Heterojunctions for Ammonia Sensing.
Alkylthio-tetrasubstituted μ-nitrido diiron phthalocyanine complexes are synthesized with n-butyl, iso-butyl, tert-butyl, and n-hexadecyl alkyl moieties. For the first time, a spectroelectrochemical investigation of μ-nitrido diiron phthalocyanines is achieved at all the redox steps. The complexes are stable in all their redox states, unlike their unsubstituted analogues. The interest of the present complexes is to prepare sensing devices by a solution processing method. Films are characterized by electronic absorption and Raman spectroscopies. Electrical measurements on resistors show the highly resistive behavior of these complexes, whatever the chain length. However, when combined with t…
Series of charge transfer complexes obtained as crystals in a confined environment
A series of charge transfer complexes (CTCs) were successfully formed by solvent free processing techniques, using the 1,2,4,5-tetracyano benzene (TCNB) as πA molecule and a series of p-dihydroquinones (H2Qs) as πD counterparts. Additionally to the classical co-evaporation techniques, we obtained CTCs in less than an hour, in a very simple confined environment, between two 100 μm – spaced glass plates. A systematical study by Raman spectroscopy on crystals highlighted the CTCs formation. Moreover, three new crystalline structures were obtained, namely TCNB-H2Q that crystallizes in columns connected to each other by H-bonds, while with the methoxy- and dimethoxy-H2Qs the CTC forms crystals w…
Electrochemical detection of the 2-isobutyl-3-methoxypyrazine model odorant based on odorant-binding proteins: The proof of concept
Abstract We developed an electrochemical assay for the detection of odorant molecules based on a rat odorant-binding protein (rOBP3). We demonstrated that rOBP3 cavity binds 2-methyl-1,4-naphtoquinone (MNQ), an electrochemical probe, as depicted from the decrease of its electrochemical signal, and deduced the dissociation constant, Kd MNQ = 0.5(± 0.2) μM. The amount of MNQ displaced from rOBP3 by 2-isobutyl-3-methoxypyrazine (IBMP), a model odorant molecule, was measured using square-wave voltammetry. The release of MNQ by competition led to an increase of the electrochemical response. In addition, this method allowed determination of the dissociation constant of rOBP3 for IBMP, Kd IBMP =…
In situ spectroelectrochemical study of the reductive coupling of benzaldehyde catalyzed by Ti(III) complexes in the presence of Mg(II)
Abstract The UV–vis spectroelectrochemical technique has been used to visualize for the first time, the formation of a trimetallic intermediate Ti(III)Mg(II)Ti(III) during the reductive coupling of benzaldehyde in the presence of electrogenerated Ti(III) and MgCl 2 . This intermediate is supposed to induce the high diastereoselectivity of the reaction. We have built a special thin layer cell adapted from the scheme proposed by A. Neudeck and L. Dunsch [‘J. Electroanal. Chem. 370 (1994) 17; J. Electroanal. Chem. 386 (1995) 135’] which allows the simultaneous recording of the cyclic voltammogram and of a great quantity of UV–vis spectra at a frequency of 1 spectrum per second by means of a …
Low Conductive Electrodeposited Poly(2,5-dimethoxyaniline) as a Key Material in a Double Lateral Heterojunction, for Sub-ppm Ammonia Sensing in Humid Atmosphere
We present a new device called a double lateral heterojunction (DLH) as an ammonia sensor in humid atmosphere. It combines polyaniline derivatives in their poor conducting state with a highly conductive molecular material, lutetium bisphthalocyanine, LuPc2. Polyaniline and poly(2,5-dimethoxyaniline) are electrodeposited on ITO interdigitated electrodes, leading to an original device that can be obtained only by electrochemistry and not by other solution processing techniques. Both polymers lead to highly conducting materials that require a neutralization step before their coverage by LuPc2. While the device based on polyaniline shows ohmic behavior, the nonlinear I- V characteristics of the…
[60]Fullerene l -Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior
International audience; A new method to link amino acid and peptide derivatives to [60]fullerene is described. It uses hydrophosphination with a secondary phosphine borane. First, the stereoselective synthesis of secondary phosphine borane amino acid derivatives was achieved by alkylation of phenylphosphine borane with gamma-iodo-alpha-amino ester reagents under phase transfer catalysis (PTC). Second, a sec-phosphine borane amino ester was saponified and coupled with alpha,gamma-diamino esters to afford the corresponding dipeptide derivatives in good yields. Finally, the hydrophosphination reaction of [60]fullerene by the sec-phosphine borane compounds was performed under PTC to obtain C-60…
New n-type molecular semiconductor–doped insulator (MSDI) heterojunctions combining a triphenodioxazine (TPDO) and the lutetium bisphthalocyanine (LuPc2) for ammonia sensing
International audience; Molecular semiconductor–doped insulator (MSDI) heterojunctions were designed using a new family of sublayers, namely triphenodioxazines (TPDO). The device obtained by combining the tetracyano triphenodioxazine bearing two triisopropylsilylethynyl moieties as a sublayer with the lutetium bisphthalocyanine (LuPc2) as a top layer showed a nonlinear current–voltage characteristic independent of the sign of the polarization, which is the signature of MSDI heterojunctions. Thus, a TPDO was used in a chemical sensor for the first time. Despite LuPc2 being the only material exposed to the atmosphere, the positive response of the device under ammonia revealed the key role pla…
The reduction mechanism of the CO group.
A detailed study of the electrochemical reduction of benzil in aqueous medium between H0=−5 and pH 11 is presented. A global 2e−, 3H+ or 2e−, 2H+ surface reaction leads to cis and trans endiols. Analysis, using the theory of the square schemes with protonations at equilibrium, shows that in all the pH range the reaction is controlled by the second electron uptake, the paths being successively H+, e− and e−, H+. The electrochemical reaction is followed by surface isomerizations whose rate constants vary from 7 to 200 s−1 for the trans/cis and from 1 to 2000 s−1 for the cis/trans transformations.
Modulating the Electrical Properties of Organic Heterojunction Devices Based On Phthalocyanines for Ambipolar Sensors.
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DNA nanofilm thickness measurement on microarray in air and in liquid using an atomic force microscope.
International audience; The measurement of the thickness of DNA films on microarray as a function of the medium (liquid, air) is gaining importance for understanding the signal response of biosensors. Thiol group has been used to attach DNA strands to gold micropads deposited on silicon surface. Atomic force microscopy (AFM) was employed in its height mode to measure the change in the pad thickness and in its force mode to measure the indentation depth of the nanofilm. A good coherence between the height and force modes is observed for the film thickness in air. The adhesion force was found to be an alternative way to measure the surface coverage of the biolayer at nanoscopic scale. However…
Comprehensive Study of Poly(2,3,5,6-tetrafluoroaniline): From Electrosynthesis to Heterojunctions and Ammonia Sensing.
In this work, we report for the first time on a comprehensive study of poly(2,3,5,6-tetrafluoroaniline) (PTFANI). Contrary to the nonfluorinated polyaniline (PANI) or its analogues bearing one fluorine atom, PTFANI is a poorly conductive material. We present a comprehensive study of the electrosynthesized PTFANI from its monomer in an acidic aqueous medium. PTFANI was fully characterized by a potential-pH diagram, spectroelectrochemistry, and electrochemical quartz crystal microbalance (EQCM) measurements, as well as by a morphological study. Combined with the X-ray photoelectron spectroscopy (XPS) analysis, it allowed us to understand the redox properties of this polymer compared to those …
Synthesis of organometallic glycopeptides and electrochemical studies to detect autoantibodies in multiple sclerosis patients' sera
Feliciana Real-Fernandez, Amelie Chamois-Colson, Jerome Bayardon, Francesca Nuti, Elisa Peroni, Maria R. Moncelli, Rita Meunier-Prest, Sylvain Juge and Anna Maria Papini Laboratory of Peptide & Protein Chemistry & Biology, Polo Scientifico, University of Florence, I-50019 Sesto Fiorentino (FI), Italy; Laboratoire de Synthese et d’Electrosynthese Organometalliques (LSEO), Universite de Bourgogne, 21068, Dijon, France
Measurements of thickness dispersion in biolayers by scanning force microscopy and comparison with spectroscopic ellipsometry analysis.
Measuring the thickness of biological films remains a difficult task when using differential measurements by atomic force microscopy (AFM). The use of microstructured substrates combined with a selective adsorption constitutes an alternative to tribological measurements. The statistical thickness analysis of biological layers, especially via the dispersion measurements, can provide a way to quantify the molecular orientation. AFM thicknesses were then compared with those obtained optically by spectroscopic ellipsometry (SE) and surface plasmon resonance enhanced ellipsometry (SPREE). The biolayers could then be modeled using a vertical gradient of optical index, which reflects height disper…
Proton Transfer versus Hydrogen Bonding: The Reduction of Ubiquinone Q2Incorporated in a Self-Assembled Monolayer in Unbuffered Aqueous Solution
The electrochemical reduction of ubiquinone Q2 (UQ2) in unbuffered aqueous media was investigated over a pH range of 2 to 11, and the results were compared to those obtained in our previous work in buffered solutions. The short isoprene chains of UQ2 were incorporated in a self-assembled monolayer. Analysis of the mechanism and a study in D2O solutions allowed us to demonstrate the important role of hydrogen bonding in the stabilization of the reduced species, also in water. If the concentration of H+ is low relative to that of the quinone, the electrochemical reaction does not proceed through proton-coupled electron transfer, as it does in buffered medium or at low pH values (pH<4.4). We p…
Electrochemical probe for the monitoring of DNA-protein interactions.
Self-assembly of thiol-terminated oligonucleotides on gold substrates provides a convenient way for DNA-functionalized surfaces. Here we describe the development of an electrochemical assay for the detection of DNA-protein interactions based on the modification of the electrochemical response of methylene blue (MB) intercalated in the DNA strands. Using a functionalized electrode with double stranded DNA carrying T3 RNA polymerase binding sequence, we show a substantial attenuation of the current upon the DNA-protein interaction. Moreover, a Langmuir binding isotherm for T3 RNA polymerase (T3 Pol) gives a dissociation constant K(D) equal to 0.46+/-0.23 microM. Such value is 100 times lower …
Electrochemical and DFT studies of the oxidative decomposition of the trihydride complexes Cp*M(dppe)H3 (M = Mo, W) in acetonitrile
International audience; A detailed electrochemical study of the oxidative decomposition of the trihydride complexes Cp*M(dppe)H3 (M = Mo, W) in acetonitrile is presented. For the Mo complex, the decomposition occurs by four different pathways involving classical and non-classical tautomers, whereas only the classical form is accessible for the W derivative. Each of the decomposition pathways has been quantitatively assessed by analyses of the linear sweep voltammograms. In addition to the previously established (B. Pleune, D. Morales, R. Meunier-Prest, P. Richard, E. Collange, J. C. Fettinger and R. Poli, J. Am. Chem. Soc., 1999, 121, 2209–2225) deprotonation, disproportionation, and H2 red…
p -Type and n -type conductometric behaviors of octachloro-metallophthalocyanine-based heterojunctions, the key role of the metal
In the present work, we determined the electrical properties of octachlorinated metallophthalocyanines with Co(II) and Cu(II) ions as metal centers. We engaged them in heterojunctions, with lutetium bisphthalocyanine as a partner. Surprisingly, cobalt and copper complexes show opposite behaviors, the first being an [Formula: see text]-type material whereas the latter is a [Formula: see text]-type material, as deduced from the response of the heterojunctions towards ammonia; showing the unusual key role played by the metal center. While the LuPc[Formula: see text]/Cu(Cl[Formula: see text]Pc) complex exhibits a negative response to ammonia, the LuPc[Formula: see text]/Co(Cl[Formula: see text…
On the interest of ambipolar materials for gas sensing
International audience; Based on the electrochemical properties of a series of metallophthalocyanines this article shows that the phthalocyanine bearing four alkoxy groups and twelve fluorine atoms behaves approximately as those with eight fluorine atoms. This indicates that the electron-donating effect of one alkoxy group balances the electro-withdrawing effect of one fluorine atom. We engaged three metallophthalocyanines, namely the octafluoro copper phthalocyanine, Cu(F8Pc), an octaester metallophthalocyanine and a phthalocyanine bearing four alkoxy groups and twelve fluorine atoms, Zn(T4F12Pc), in building original conductometric transducers that are Molecular Semiconductor – Doped Insu…
A biometic olfactory based biosensor combining electrochemistry and odorant-binding
A biometic olfactory based biosensor combining electrochemistry and odorant-binding. Food Factory 2012
β-Aminobutyric Acid (BABA)-Induced Resistance in Arabidopsis thaliana: Link with Iron Homeostasis
International audience; Bêta-Aminobutyric acid (BABA) is a nonprotein amino acid inducing resistance in many different plant species against a wide range of abiotic and biotic stresses. Nevertheless, how BABA primes plant natural defense reactions remains poorly understood. Based on its structure, we hypothesized and confirmed that BABA is able to chelate iron (Fe) in vitro. In vivo, we showed that it led to a transient Fe deficiency response in Arabidopsis thaliana plants exemplified by a reduction of ferritin accumulation and disturbances in the expression of genes related to Fe homeostasis. This response was not correlated to changes in Fe concentrations, suggesting that BABA affects the…
Performance of interdigitated nanoelectrodes for electrochemical DNA biosensor.
An electrochemical methodology for bio-molecule sensing using an array of well-defined nanostructures is presented. We describe the fabrication by e-beam lithography of nanoelectrodes consisting of a 100 micro m x 50 micro m area containing interdigitated electrodes of 100 nm in width and interelectrode distance of 200 nm. Sensitivity and response time of the nanoelectrodes are compared to the responses of macro- and microelectrodes. The specificity of the sensor is studied by modifying the gold electrodes with DNA. The technique enables to characterize both single and double-stranded DNA of 15 nucleotides. A special electrochemical cell is adapted to control the temperature and measure the…
CCDC 1994293: Experimental Crystal Structure Determination
Related Article: Ali Sanda Bawa, Rita Meunier-Prest, Yoann Rousselin, Jean-Pierre Couvercelle, Christine Stern, Bernard Malézieux, Marcel Bouvet|2021|CrystEngComm|23|6418|doi:10.1039/D1CE00929J
CCDC 2063384: Experimental Crystal Structure Determination
Related Article: Ali Sanda Bawa, Rita Meunier-Prest, Yoann Rousselin, Jean-Pierre Couvercelle, Christine Stern, Bernard Malézieux, Marcel Bouvet|2021|CrystEngComm|23|6418|doi:10.1039/D1CE00929J
CCDC 1994294: Experimental Crystal Structure Determination
Related Article: Ali Sanda Bawa, Rita Meunier-Prest, Yoann Rousselin, Jean-Pierre Couvercelle, Christine Stern, Bernard Malézieux, Marcel Bouvet|2021|CrystEngComm|23|6418|doi:10.1039/D1CE00929J
CCDC 1497477: Experimental Crystal Structure Determination
Related Article: Amélie Wannebroucq, Rita Meunier-Prest, Jean-Claude Chambron, Claire-Hélène Brachais, Jean-Moïse Suisse, Marcel Bouvet|2017|RSC Advances|7|41272|doi:10.1039/C7RA05325H