A5040069552- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Crystallography and molecular interactions
- Metal-Organic Frameworks: Synthesis and Applications
- Supramolecular Chemistry and Complexes
- Covalent Organic Framework Applications
- Chemistry and Chemical Engineering
- Hydrocarbon exploration and reservoir analysis
- Supramolecular Self-Assembly in Materials
- Innovative Microfluidic and Catalytic Techniques Innovation
- Catalytic Processes in Materials Science
- Photoreceptor and optogenetics research
- Mesoporous Materials and Catalysis
- Machine Learning in Materials Science
- Nanocluster Synthesis and Applications
- Phenothiazines and Benzothiazines Synthesis and Activities
- Surface Chemistry and Catalysis
- Porphyrin Metabolism and Disorders
- Membrane Separation and Gas Transport
- Nanopore and Nanochannel Transport Studies
- HIV/AIDS drug development and treatment
- Biochemical and Molecular Research
- Analytical Chemistry and Chromatography
- Magnetism in coordination complexes
- Graphene and Nanomaterials Applications
Kyoto University
2016-2020
Merck & Co., Inc., Rahway, NJ, USA (United States)
2020
Centre National de la Recherche Scientifique
2013-2019
Université de Strasbourg
2013-2019
Laboratoire des Sciences de l’Information et de la Communication
2014
Chimie Moléculaire, Macromoléculaire, Matériaux
2013
Chimie de la Matière Complexe
2013
Trinity College Dublin
2010
Abstract Designed porosity in coordination materials often relies on highly ordered crystalline networks, which provide stability upon solvent removal. However, the requirement for crystallinity impedes control of higher degrees morphological versatility, or processing. Herein, we describe a supramolecular approach to synthesis amorphous polymer with controlled microporosity. The strategy entails use robust metal–organic polyhedra (MOPs) as porous monomers polymerization reaction. Detailed...
The upbuilding of dirhodium tetracarboxylate paddlewheels into porous architectures is still challenging because the inertness equatorial carboxylates for ligand-exchange reaction. Here we demonstrate synthesis a new family metal-organic cuboctahedra by connecting units through 1,3-benzenedicarboxylate and assembling as solids. Carbon monoxide nitric oxide were strongly trapped in internal cavity thanks to strong affinity unsaturated axial coordination sites centers.
Metal-organic polyhedra (MOP) are ultrasmall (typically 1-4 nm) porous coordination cages made from the self-assembly of metal ions and organic linkers amenable to chemical functionalization its periphery; however, it has been challenging implement postsynthetic due their instability. Herein, we report use chemistries covalent postsynthetically functionalize external surface ≈2.5 nm stable Rh(II)-based cuboctahedra through Rh-Rh paddlewheel units or linkers, respectively. We demonstrate that...
Porous molecular cages have a characteristic processability arising from their solubility, which allows incorporation into porous materials. Attaining solubility often requires covalently bound functional groups that are unnecessary for porosity and ultimately occupy free volume in the materials, decreasing surface areas. Here, method is described takes advantage of coordination bonds metal-organic polyhedra (MOPs) to render insoluble MOPs soluble by reversibly attaching an...
Assemblies of lantern-type metal–organic polyhedra are found to show gate-opening gas adsorption depending on how they treated with solvents.
Crystalline suspensions of monoclonal antibodies (mAbs) have great potential to improve drug substance isolation and purification on a large scale be used for delivery via high-concentration formulations. mAb are expected enhanced chemical physical properties relative solutions delivered intravenously, making them attractive candidates subcutaneous delivery. In contrast small molecules, the development protein crystalline is not widely approach in pharmaceutical industry. This mainly due...
Combinations of two enantiomerically pure organic tectons 1 and 3 with either Zn(ii) or Cu(ii) cations lead to the formation four homochiral 3D networks among which two, 1-Cu 3-Cu, are robust porous crystals displaying cavities permanent microporosity. 3-Cu capture 66% 20% l- d-tryptophan, respectively, after 30 min adsorption.
Various synthetic routes to 2-isopropyl-4-methoxyphenol 3, the phenol core of Gefapixant citrate (MK-7264), are described, which provide better alternatives initial four-step supply route. These new include a coumarin fragmentation approach in flow, rhenium-catalyzed isopropylation mequinol, and bromination/methoxylation 2-isopropylphenol. After exploring several approaches, robust two-step process for preparation 3 from commodity starting material 2-isopropylphenol was developed. The...
Abstract Porous molecular cages have a characteristic processability arising from their solubility, which allows incorporation into porous materials. Attaining solubility often requires covalently bound functional groups that are unnecessary for porosity and ultimately occupy free volume in the materials, decreasing surface areas. Here, method is described takes advantage of coordination bonds metal–organic polyhedra (MOPs) to render insoluble MOPs soluble by reversibly attaching an...
Upon combining enantiomerically pure bis-monodentate organic tectons with ZnSiF6, homochiral 3D cuboid architectures displaying chiral channels are formed.
The reversible switching between the open and closed states of a molecular turnstile can be addressed by emission spectroscopy.
Cooperative gas uptake in metal–organic cages is tuned using supramolecular chemistry.
An achiral organic tecton bearing four coordinating sites of the pyridyl type leads to formation iso-structural 3D helical coordination polymers when combined with Co(SCN)2 and Fe(SCN)2 neutral complexes. Their occurs during self-assembly process in solid state, which crystals composed homochiral polymers.
A scalable two-pot sulfonamidation through the process has been developed for synthesis of gefapixant citrate, a P2X3 receptor antagonist that is under investigation treatment refractory and unexplained chronic cough. Direct conversion diaryl ether precursor to sulfonyl chloride intermediate using chlorosulfonic acid, followed by with aqueous ammonia hydroxide, provided desired sulfonamide in high yield. pH-swing crystallization allowed formation transient acetonitrile solvate enables...
Optical reading of the open and closed states a molecular turnstile.
The use of compound 1 as an enantiomerically pure neutral and rigid organic linear tecton bearing two divergently oriented monodentate coordinating sites appended with chiral centres the same (S) configuration leads, in presence metal complexes behaving either a (Cu(hfac)2, Cu(OAc)2) or V-shaped (HgCl2) 2-connecting node 4-connecting square (NiCl2), to formation four homochiral 1- 2-D coordination polymers.
The development of a safe, robust, and efficient manufacturing route for the synthesis diaminopyrimidine 1, key intermediate to gefapixant citrate (MK-7264), is described. A full mechanistic understanding cyclization step in presence guanidine was established by performing isotopic labeling experiments identification impurities. Guided understanding, further attempts modify reaction employing additives reduce triazine (9) formation loading will also be presented. This newly developed method...
The development of a sustainable commercial salt formation process for gefapixant citrate (MK-7264), an investigational new P2X3 antagonist the treatment chronic cough, is described. Due to low solubility free base, first-generation was slurry-to-slurry with poor quality control, wherein impurities were not well rejected and unreacted base often persisted in produced. controlled crystallization from homogeneous solution, which overcame these deficiencies, complicated by constraints daunting...
Combinations of three enantiomerically pure organic chiral linear tectons bearing two divergently oriented pyridyl units as coordinating poles with HgCl2 a two-connecting V-shape metallatecton offering free coordination sites lead to the formation stair-type 1D mercury networks.
By combining enantiomerically pure tectons with Cd(NO<sub>3</sub>)<sub>2</sub>, a series of six new homochiral luminescent coordination networks are formed. The dimensionality and crystal packing the latter modulated by both nature chiral side chains crystallization solvents.
Porous molecular cages have a characteristic processability arising from their solubility, which allows incorporation into porous materials. Attaining solubility often requires covalently bound functional groups that are unnecessary for porosity, and ultimately occupy free volume in the materials decrease surface areas. Here, we describe method takes advantage of coordination bonds metal-organic polyhedra (MOPs) to render insoluble MOPs soluble by reversibly attaching an alkyl-functionalized...
During large-scale crystallization of the ethyl ester (EE) starting material Doravirine (MK-1439) (Huang et al. ACS Infectious Dis. 2020, 6, 64–73) four out nine batches exhibited unique infrared spectra upon release testing and atypical powder X-ray diffraction (PXRD) patterns not conforming to target crystalline phase, Form 1. This work presents investigations triggered within MSD's laboratories on polymorphism EE strategy employed for identifying nature form impurity understanding its...
Structural deformation in response to gas sorption is rarely observed for porous molecular solids, when compared framework materials. Here, we describe the effect of chemical modification on exterior lantern-type metal-organic cages emergence and then disappearance cooperative uptake. The results suggest that supramolecular design ligands can be used reveal this behaviour.