Fluorinated liquid crystals formed by halogen bonding.
New, halogen-bonded fluorinated mesogens are reported; the expected microphase separation associated with perfluoroalkyl chains is surprisingly absent in the mesophase.
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Biomedical subjects
Pierangelo Metrangolo
Publications and source records attributed to Pierangelo Metrangolo.
Molecular and supramolecular homochirality: enantiopure perfluorocarbon rotamers and halogen-bonded fluorous double helices.
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Metric engineering of supramolecular Borromean rings.
Two homologues of supramolecular Borromean rings were obtained based on the halogen-bonding-driven self-assembly of iodide ions with telechelic diiodoperfluoroalkanes.
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A halogen-bonding-based heteroditopic receptor for alkali metal halides.
A new heteroditopic receptor for alkali metal halides has been designed and synthesized. It is comprised of a well-established motif for cation binding and a motif for halogen-bonding-based anion recognition processes. The single-crystal X-ray structure of the complex between the heteroditopic receptor and sodium iodide is reported. Thanks to the cooperativity of metal coordination and the strong I-...I halogen bonding, the ion pair is fully separated. The boosting effect of the binding of the anion through halogen bonding on the coordination of the cation by the receptor has been proved also in solution by NMR experiments. The selectivity of the new heterotopic receptor toward different alkali metal halides has been tested by ESI mass experiments.
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Spontaneous resolution in a halogen bonded supramolecular architecture.
The halogen bonding driven self-assembly of 1,8-diiodoperfluorooctane and N,N,N',N'-tetramethyl-p-phenylenediamine induces the formation of a chiral and enantiopure co-crystal wherein the fluorinated chains adopt an unusual gauche arrangement.
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Halogen bonding based recognition processes: a world parallel to hydrogen bonding.
Halogen bonding is the noncovalent interaction between halogen atoms (Lewis acids) and neutral or anionic Lewis bases. The main features of the interaction are given, and the close similarity with the hydrogen bonding will become apparent. Some heuristic principles are presented to develop a rational crystal engineering based on halogen bonding. The focus is on halogen-bonded supramolecular architectures given by halocarbons. The potential of the interaction is shown by useful applications in the field of synthetic chemistry, material science, and bioorganic chemistry.
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Metric engineering of perfluorocarbon-hydrocarbon layered solids driven by the halogen bonding.
The halogen bonding driven self-assembly of 1,4-dicyanobutane and 1,6-dicyanohexane with a range of perfluorinated telechelic diiodoalkanes yields layered 1D, infinite chain co-crystals. The structure and metrics of these co-crystals are remarkably predictable.
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Halogen bonding and pi...pi stacking control reactivity in the solid state.
The halogen bonding and the pi...pi stacking interactions induce the noncovalent self-assembly of modules into photoreactive supramolecular architecture. The pi...pi interaction pre-organizes the template, and the halogen bonding aligns the olefins to conform to the topochemical principle for photoreaction. The UV irradiation of the crystal resulted in a cyclization product with quantitative yield and stereospecificity.
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N.Br halogen bonding: one-dimensional infinite chains through the self-assembly of dibromotetrafluorobenzenes with dipyridyl derivatives.
The N.Br halogen bonding drives the self-assembly of 1,4-dibromotetrafluorobenzene (1 a) and its 1,3 or 1,2 analogues (1 b,c, respectively) with dipyridyl derivatives 2 a,b. The isomeric supramolecular architectures 3 a-f are obtained as cocrystals that are stable in the air at room temperature. The solid-state features of these 1D infinite chains 3 have been fully characterized by single-crystal X-ray, Raman, and IR analyses. The occurrence of N.Br halogen bonding in solution has been detected with (19)F NMR spectroscopy. The N.Br halogen bonding is highly selective and directional and the geometry of the single strands of noncovalent copolymers 3 is programmed by the geometry of halogen-bonding donor and acceptor sites on the starting modules. The composition and topology of the instructed networks can be predicted with great accuracy. Experiments of competitive cocrystal formation established the strength of the N.Br interaction relative to other halogen bondings and the ability of different modules 1 to be involved in site-selective supramolecular syntheses.
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