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A series of neutral tetradentate halogen bonding (XB) macrocycles, comprising of two bis-iodotriazole XB donors were synthesised in 60–70% yields via a stepwise CuAAC-mediated cyclisation strategy. Extensive 1H NMR anion titration experiments reveal halide binding affinities are critically dependent on the substitution pattern of the xylyl spacer unit. The meta-substituted macrocycle remarkably displays cooperative tetradentate XB-halide anion recognition in highly competitive 40% aqueous-organic D2O/acetone-d6 (40 : 60, v/v) solvent mixtures. Integration of para-xylyl and naphthyl spacer units generates extended macrocyclic cavities, capable of selective oxalate recognition. Furthermore, preliminary fluorescence exeperiments reveal dicarboxylate specific sensing can be achieved through monitoring of the naphthylene centred emission. [ABSTRACT FROM AUTHOR]

PO⋯X and N⋯X halogen bonds in combination with π-stacking interactions lead to the sorting of π-extended R- and S-isomers. Theoretical calculations point to a positive synergistic effect between the π-interactions and the halogen bonds to be the origin of such phenomena. As a result, enantiomeric building blocks form homoleptically connected quadrangular structures. [ABSTRACT FROM AUTHOR]

Two decades ago, halogen bonding attracted considerable attention as a new type of non-covalent interaction and has now emerged as an important supramolecular tool for crystal engineering, demonstrating its ability to self-assemble low affinity entities. Specific features of halogen bonds have been subsequently harnessed in biological and material sciences to give rise to elegant functional systems with a wide range of applications. In this highlight, we focused on new concepts in polymer science, electrochemistry, electronic and sensing materials. Recent findings on the use of halogenated compounds for transmembrane transport are also discussed, together with a short summary of the current understanding of the nature of the halogen bond, in the light of modern computational tools and energy decomposition. [ABSTRACT FROM AUTHOR]

Herein we demonstrate that three dimensional supramolecular polymerization networks were constructed both in solution and in the solid state by the combination of pillar[5,6]arene-based host–guest complexes and 1,4-diiodotetrafluorobenzene involving halogen bonding systems. [ABSTRACT FROM AUTHOR]

Diphenylacetylene (tolan) derivatives with self-complementary aryl halides and halogen bond-accepting nitriles form 2D bricklayer packing motifs when halogen bonding occurs. When halogen bonding is absent, as occurred with fluorinated aryl bromides, the molecules adopt other packing motifs. These results suggest halogen bonding is potentially useful for producing rarely observed 2D bricklayer motifs in organic semiconductors. [ABSTRACT FROM AUTHOR]

Affinity materials based on halogen bonds turned out to be a powerful tool for the molecular recognition of acetone or related carbonyl compounds in the presence of ubiquitous protic molecules. The superior selectivity and sensitivity were found by the gravimetric detection of volatile organic compounds by quartz crystal microbalances. [ABSTRACT FROM AUTHOR]