scholarly journals Superior anion induced shuttling behaviour exhibited by a halogen bonding two station rotaxane

2016 ◽  
Vol 7 (8) ◽  
pp. 5171-5180 ◽  
Author(s):  
Timothy A. Barendt ◽  
Sean W. Robinson ◽  
Paul D. Beer
Keyword(s):  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Translational Motion ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Recognition Site ◽  
Naphthalene Diimide

Two bistable halogen and hydrogen bonding-naphthalene diimide [2]rotaxanes have been prepared and the system incorporating a halogen bond donor anion recognition site is demonstrated to exhibit superior anion induced translational motion of the macrocyclic wheel component relative to the hydrogen bonding analogue.

scholarly journals Anion Recognition by Neutral and Cationic Iodotriazole Halogen Bonding Scaffolds

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 798
Author(s):  
Iñigo Iribarren ◽  
Goar Sánchez-Sanz ◽  
Cristina Trujillo
Keyword(s):  
Density Functional ◽  
Computational Study ◽  
Halogen Bond ◽  
Anion Recognition ◽  
Lone Pair ◽  
Halogen Bonding ◽  
Binding Energies ◽  
Bond Critical Point ◽  
Density Values ◽  
Intramolecular Hydrogen

A computational study of the iodide discrimination by different neutral and cationic iodotriazole halogen bonding hosts was carried out by means of Density Functional Theory. The importance of the size of the scaffold was highlighted and its impact observed in the binding energies and intermolecular X⋯I distances. Larger scaffolds were found to reduce the electronic repulsion and increase the overlap between the halide electron lone pair and the corresponding I-C antibonding orbital, increasing the halogen bonding interactions. Additionally, the planarity plays an important role within the interaction, and can be tuned using hydroxyl to perform intramolecular hydrogen bonds (IMHB) between the scaffold and the halogen atoms. Structures with IMHB exhibit stronger halogen bond interactions, as evidenced by the shorter intramolecular distances, larger electron density values at the bond critical point and more negative binding energies.

scholarly journals Cationic all-halogen bonding rotaxanes for halide anion recognition

2017 ◽  
Vol 203 ◽  
pp. 245-255 ◽  
Author(s):  
Xiaoxiong Li ◽  
Jason Y. C. Lim ◽  
Paul D. Beer
Keyword(s):  
Halogen Bond ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Anion Binding ◽  
Halide Anion ◽  
H Nmr ◽  
Organic Solvent Media ◽  
Synthetic Strategy ◽  
Anion Selectivity ◽  
Active Metal

A family of cationic halogen bonding [2]rotaxanes have been synthesised via an active-metal template synthetic strategy. 1H NMR spectroscopic anion titration investigations reveal these interlocked host systems recognize halides selectively over oxoanions in aqueous–organic solvent media. Furthermore, systematically modulating the rigidity and size of the rotaxanes’ anion binding cavities via metal complexation, as well as by varying the number of halogen bond-donor groups in the axle component, was found to dramatically influence halide anion selectivity.

scholarly journals Tripodal halogen bonding iodo-azolium receptors for anion recognition

RSC Advances ◽  
2017 ◽  
Vol 7 (19) ◽  
pp. 11253-11258 ◽  
Author(s):  
Sheila Ruiz-Botella ◽  
Pietro Vidossich ◽  
Gregori Ujaque ◽  
Eduardo Peris ◽  
Paul D. Beer
Keyword(s):  
Hydrogen Bonding ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Anion Binding ◽  
Binding Properties

The preparation and anion binding properties of 1,3,5-tri-substituted benzene platform-based tripodal receptors containing halogen bonding (XB) iodo-imidazolium and iodo-triazolium motifs, and hydrogen bonding (HB) analogues are described.

scholarly journals Evidence for Halogen Bond Covalency in Acyclic and Interlocked Halogen-Bonding Receptor Anion Recognition

2014 ◽  
Vol 137 (1) ◽  
pp. 499-507 ◽  
Author(s):  
Sean W. Robinson ◽  
Chantal L. Mustoe ◽  
Nicholas G. White ◽  
Asha Brown ◽  
Amber L. Thompson ◽  
...  
Keyword(s):  
Halogen Bond ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Bond Covalency

scholarly journals The intramolecular hydrogen bonded–halogen bond: a new strategy for preorganization and enhanced binding

2018 ◽  
Vol 9 (26) ◽  
pp. 5828-5836 ◽  
Author(s):  
Asia Marie S. Riel ◽  
Daniel A. Decato ◽  
Jiyu Sun ◽  
Casey J. Massena ◽  
Morly J. Jessop ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
New Strategy ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

Intramolecular hydrogen bonding directly to halogen bond donors preorganizes molecular structure and strengthens halogen bonding.

scholarly journals Neutral iodotriazole foldamers as tetradentate halogen bonding anion receptors

2017 ◽  
Vol 53 (16) ◽  
pp. 2483-2486 ◽  
Author(s):  
Arseni Borissov ◽  
Jason Y. C. Lim ◽  
Asha Brown ◽  
Kirsten E. Christensen ◽  
Amber L. Thompson ◽  
...  
Keyword(s):  
Halogen Bond ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Chiral Discrimination ◽  
Anion Receptors

A tetradentate halogen bond donor foldamer receptor framework is shown to exhibit enhanced anion recognition and chiral discrimination properties.

scholarly journals Exploring the Halogen-Bonded Cocrystallization Potential of a Metal-Organic Unit Derived from Copper(ii) Chloride and 4-Aminoacetophenone

Materials ◽  
2020 ◽  
Vol 13 (10) ◽  
pp. 2385
Author(s):  
Vinko Nemec ◽  
Katarina Lisac ◽  
Marin Liović ◽  
Ivana Brekalo ◽  
Dominik Cinčić
Keyword(s):  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Building Blocks ◽  
Supramolecular Interactions ◽  
X Ray Diffraction ◽  
Square Planar ◽  
Metal Organic ◽  
Acetyl Group ◽  
Conventional Solution

In this work, we describe a novel halogen-bonded metal-organic cocrystal involving a square-planar Cu(ii) complex and 1,4-diiodotetrafluorobenzene (14tfib) by utilizing an amine ligand whose pendant acetyl group enables halogen bonding. The cocrystal was prepared by both mechanochemical synthesis (liquid-assisted grinding) and the conventional solution-based method. Crystal structure determination by single crystal X-ray diffraction revealed that the dominant supramolecular interactions are the I···O halogen bond between 14tfib and CuCl2(aap)2 building blocks, and the N–H···Cl hydrogen bonds between CuCl2(aap)2 molecules. The combination of halogen and hydrogen bonding leads to the formation of a 2D network. Overall, this work showcases an example of the possibility for extending the complexity of metal-organic crystal structures by using halogen bonding in a way that does not affect other hydrogen bonding synthons.

Superior perrhenate anion recognition in water by a halogen bonding acyclic receptor

2015 ◽  
Vol 51 (17) ◽  
pp. 3686-3688 ◽  
Author(s):  
Jason Y. C. Lim ◽  
Paul D. Beer
Keyword(s):  
Halogen Bond ◽  
Anion Recognition ◽  
Halogen Bonding ◽  
Anion Binding ◽  
Fluorescence Sensing

The first example of perrhenate anion binding and fluorescence sensing in water by a halogen bond donor is reported.

scholarly journals Halogen-Bonding-Driven Self-Assembly of Solvates of Tetrabromoterephthalic Acid

Crystals ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 198
Author(s):  
Nucharee Chongboriboon ◽  
Kodchakorn Samakun ◽  
Winya Dungkaew ◽  
Filip Kielar ◽  
Mongkol Sukwattanasinitt ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Phase Transitions ◽  
Self Assembly ◽  
Solid Phase ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Cooperative Effect ◽  
Hydrogen Bonding Interactions ◽  
Solvent Molecules

Halogen bonding is one of the most interesting noncovalent attractions capable of self-assembly and recognition processes in both solution and solid phase. In this contribution, we report on the formation of two solvates of tetrabromoterephthalic acid (H2Br4tp) with acetonitrile (MeCN) and methanol (MeOH) viz. H2Br4tp·2MeCN (1MeCN) and H2Br4tp·2MeOH (2MeOH). The host structures of both 1MeCN and 2MeOH are assembled via the occurrence of simultaneous Br···Br, Br···O, and Br···π halogen bonding interactions, existing between the H2Br4tp molecular tectons. Among them, the cooperative effect of the dominant halogen bond in combination with hydrogen bonding interactions gave rise to different supramolecular assemblies, whereas the strength of the halogen bond depends on the type of hydrogen bond between the molecules of H2Br4tp and the solvents. These materials show a reversible release/resorption of solvent molecules accompanied by evident crystallographic phase transitions.

Co-Crystallisation of 1,4-Diiodotetrafluorobenzene with Three Different Symmetric Dipyridylacetylacetone Isomers Produces Four Halogen-Bonded Architectures

2017 ◽  
Vol 70 (5) ◽  
pp. 594 ◽  
Author(s):  
Joshua J. Brown ◽  
Aidan J. Brock ◽  
Michael C. Pfrunder ◽  
Julia P. Sarju ◽  
Abigail Z. Perry ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Three Dimensional ◽  
Halogen Bonding ◽  
Supramolecular Interactions ◽  
Ambient Conditions ◽  
Supramolecular Architectures ◽  
Crystallisation Behaviour ◽  
Π Stacking

The co-crystallisation behaviour of three symmetrical dipyridylacetylacetone ligands (1,3-di(2-pyridyl)-1,3-propanedione (o-bppdH), 1,3-di(3-pyridyl)-1,3-propanedione (m-bppdH), and 1,3-di(4-pyridyl)-1,3-propanedione (p-bppdH)), with the linear halogen-bond donor 1,4-diiodotetrafluorobenzene (1,4-DITFB) has been investigated. The reaction of these components under ambient conditions in a 1 : 1 stoichiometry produced four halogen-bonded assemblies ([o-bppdH·1,4-DITFB, [m-bppdH·1,4-DITFB], [2(m-bppdH)·1,4-DITFB], and [p-bppdH·1,4-DITFB]). The combination of multiple supramolecular interactions including halogen bonding, hydrogen bonding, and π-stacking produces a range of supramolecular architectures, including one-, two-, and three-dimensional motifs. The crystal structure of m-bppdH is also reported.

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