2018
DOI: 10.1021/acs.cgd.7b01693 View full text |Buy / Rent full text
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Abstract: Over the past few decades, the tren [tris(2-aminoethyl)amine] skeleton has materialized as one of the supreme anion binding building blocks demonstrating a strong interplay among topology, complementarity, cooperativity, and coordination. However, anion recognition by modest tren-based unsubstituted aromatic urea has been underexplored, mainly due to the deficiency of π-acidic or electronwithdrawing aryl terminals. This report establishes an infrequent hexameric neutral receptor-anion-water molecular self-asse… Show more

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“…Continuing our group’s pursuit in the field of substituent driven anionic/hydrated anionic supramolecular self-assemblies of acyclic receptors, herein we develop a class of nitro-phenyl functionalized comparatively less cooperative and more challenging positional isomeric linear bis-urea receptors L 1 – L 3 (Scheme ), derived from the least converging aromatic diamine ( para -phenylenediamine) to investigate the coordination behavior with anions/hydrated anions in neutral form. Structural studies reveal that both para -isomer ( L 1 ) and meta -isomer ( L 1 ) are capable of (HCO 3 ) 2 -dimer entrapment either by fluoride or hydroxide induced fixation of atmospheric CO 2 in complexes 1a , 2a , and 2b .…”
Section: Introductionmentioning
“…Analysis of crystal packing in pharmaceuticals, their homologues, polymorphs, co-crystals, and solvates gives one information about preferable synthons that could appear in a binding pocket occupied with this drug (although some weak interactions can be over-, or under-estimated). Data knowledge about typical water associates in crystals of small molecules is important for biochemistry as similar hydrate architectures were found in crystals of inorganic, organic, and macromolecular compounds [40,41].…”
Section: Search On Hydrogen-bond Motifsmentioning
“…Analysis of solvate connectivity and the most abundant motifs (if any) formed by solvent molecules is similar to that described above for the investigation of other synthons and supramolecular associates. The practical meaning of results obtained for material chemistry, biochemistry, and the pharmaceutical industry are based on the fact that similar hydrate architectures were found in crystals of both inorganic, organic, coordination, and even macromolecular compounds [40,41]. H-bonding between a complex and an outer sphere solvent can lead to additional quenching in luminescent materials that are unfavorable for the task-specific design of optical materials [283,284].…”
Section: Analysis Of the Local Connectivity Of A Solventmentioning
“…In biomineralized materials surrounded by planar oxyanions, one of the major components is carbonate, in particular working as a buffer in blood and the exoskeletons of radiolaria, where in the form of acetyl coenzyme A acetate anion, it is exploited by the organisms. , Due to the increased ingestion of fossil fuels by automobiles, industries, etc. that is the foremost cause of a major rise in atmospheric CO 2 concentration , there is a demand for the effectual activation and fixation of atmospheric CO 2 into green chemicals. Up to now, several structurally preorganized neutral or protonated anion receptors having a tripodal cavity with various −NH functionalities have been approved. In the literature, in comparison to tripodal receptors the use of dipodal receptors toward anion recognition is common, as the dipodal receptor scaffolds are comprised of a smaller number of coordination sites and also exhibit less flexibility and more rigidity. Nevertheless, few dipodal anion receptors having urea/thiourea functionalization resulting from preorganized diamine over isomeric aromatic diamines have been reported in the literature by different groups and also by our group. , …”
Section: Introductionmentioning
“…44 The encapsulation of larger tetrahedral sulfate oxyanion is very much anticipated inside the unimolecular capsular assembly, as it is present as a contaminant in drinking water as well as acts as a pollutant in nuclear and radioactive waste, which hampers the vitrification process. 45,29 Thus far, numerous tripodal oxyurea/thiourea receptors consisting of one or more terminal aryl substitutions have been widely reported by Custelcean 15 In our ongoing effort in the field of anion-receptor chemistry to encapsulate the hydrated/ solvated/cation-triggered anionic guests into the host capsules, 46−56 herein we report the cation-triggered systematic encapsulation of smaller (fluoride) to larger halides (chloride, bromide) as well as planar (planar) and tetrahedral (sulfate) oxyanions inside the tris-naphthyl thiourea receptor cavity via 1:1 unimolecular host−guest complexation mode. Most importantly, this report delivers the first anion binding crystallographic evidence of one of the simplest tren-based unsubstituted highly electron-rich thiourea derivatives L, which was first synthesized by Wu et al in 1999, 17 that demonstrated the only solution state oxyanion binding.…”
Section: Introductionmentioning