This critical review covers advances in anion complexation chemistry related to receptors based on organic frameworks in the years 2005–2006. The review covers anion receptors that employ amides and thioamides, pyrroles and indoles, ureas and thioureas, ammonium, guanidinium, imidazolium, and receptors containing hydroxyl groups. There is a discussion of anion templated assembly, followed by a short section outlining modelling studies of these systems. (226 references.)

Anion receptors based on organic frameworks: highlights from 2005 and 2006

This tutorial review examines the potential of anions, in particular sulfate, to template the formation of complex molecular architectures. Until recently, sulfate has been largely overlooked in this area and the examples described herein demonstrate this anion’s versatility in templating the formation of a diverse range of molecular systems including macrocycles, helixes, molecular capsules, interpenetrated and interlocked assemblies such as catenanes. In addition sulfate has been shown to template the formation of interpenetrated structures on a range of surfaces including gold, polystyrene beads and silicate nanoparticles, highlighting the potential of this anion in the fabrication of functional sensory devices exhibiting highly selective binding behaviour.

Sulfate anion templation of macrocycles, capsules, interpenetrated and interlocked structures

The indolocarbazoles are an important class of nitrogen heterocycles which has evolved significantly in recent years, with numerous studies focusing on their diverse biological effects, or targeting new materials with potential applications in organic electronics. This review aims at providing a broad survey of the chemistry and properties of indolocarbazoles from an interdisciplinary point of view, with particular emphasis on practical synthetic aspects, as well as certain topics which have not been previously accounted for in detail, such as the occurrence, formation, biological activities, and metabolism of indolo[3,2-b]carbazoles. The literature of the past decade forms the basis of the text, which is further supplemented with older key references.

Chemistry and Properties of Indolocarbazoles

Isophthalamides and 2,6-dicarboxamidopyridines with pendant indole groups: a ‘twisted’ binding mode for selective fluoride recognition

A new series of indolocarbazole-quinoxalines (ICQ, receptors 6 and 7) are prepared and characterized for effective fluoride and acetate anion sensing. The new indole-based system has a highly flat rigid structure with a large π system, and exhibits high binding affinity and sensitivity for acetate and fluoride anions. Receptors 6 and 7 give abundant and unique spectral features in dimethyl sulfoxide (DMSO). Both fluoride and acetate anions cause a bathochromic shift of the absorption peaks of receptor 7 in DMSO, whereas only fluoride anion results in a remarkable shift of the absorption peak of receptor 6 in DMSO. Receptors 6 and 7 can also operate as efficient colorimetric sensors for naked-eye detection of fluoride and acetate anions, and their combined use also offers a simple way for distinguishing these two anions by the naked-eye. The analysis of a Job's plot for the binding of receptor 7 and F−, single crystal structures of 7·TBACl and 7·TBACH3COO confirm 1 : 1 binding stoichiometry. Notably, the ICQ system offers novel and excellent receptors for acetate anion both in solution and in crystalline solid through the formation of two hydrogen bonds.

Synthesis and characterization of indolocarbazole-quinoxalines with flat rigid structure for sensing fluoride and acetate anions

Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions

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Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions