Dynamic covalent functionality has been acknowledged as a powerful tool for the construction of organised architectures, the reversible nature thermodynamically facilitates self-control and self-correction. The use of boronic acids complexation with diols and their congeners has already shown great promise in realising and developing reversible boron-containing multicomponent systems with dynamic covalent functionality. The structure-directing potential has lead to the development of a variety of self-organisation involving not only macrocycles, cages and capsules, but also porous covalent organic frameworks and polymers. Structure controls as well as remarkable synthesis are highlighted in this feature article.

In this feature article the use of boronic acids to monitor, identify and isolate analytes within physiological, environmental and industrial scenarios is discussed. Boronic acids recognise diol motifs through boronic ester formation and interact with anions generating boronates, as such they have been exploited in sensing and separation protocols for diol appended molecules such as saccharides and anions alike. Therefore robust molecular sensors with the capacity to detect chosen molecules selectively and signal their presence continues to attract substantial attention, and boronic acids have been exploited with some success to monitor the presence of various analytes. Reversible boronic acid-diol interactions have also been exploited in boron affinity chromatography realising new separation domains through the same binding events. Boronic acid diol and anion interactions pertaining to sensing and separation are surveyed.

Current progress on hierarchical supramolecules using boronic acids has been highlighted in this feature article. Boronic acids can participate in “click reactions” with diols and their congeners with dynamic covalent functionality. By comprehensively exploring versatile sequential boronate esterification linkages between plural boronic acid-appended molecules and multiple hydroxyl counterparts, not only versatile supramolecular polymers but also structurally well-defined network nanostructures have been developed. In addition orthogonal interactions such as dative bonds of the boron center with Lewis bases have led to the formation of hierarchical nano/microstructures. Boronate systems have the potential to be used as materials for smart gels, chemosensors, active architectures for electronics, heterogeneous catalysts, chemical-stimulus responsive systems for drug delivery, etc. Here, we fully discuss the feasibility of the structure-directing ability of boronic acids from the standpoint of the generation of new smart materials.

Novel boron–dibenzopyrromethene dyes with thienyl-cyanoacrylic acid units were synthesized and characterized for application in dye-sensitized solar cells (DSSCs); the dyes feature intense absorption bands in the longer wavelength region with λ_max values of 647 nm (ε = 1.57 × 10⁵ M⁻¹ cm⁻¹) for 1, which has two anchoring units, 660 nm (ε = 1.09 × 10⁵ M⁻¹ cm⁻¹) for regioisomer 2, and 644 nm (ε = 1.39 × 10⁵ M⁻¹ cm⁻¹) for 3, which has a single anchoring unit. Density functional theory (DFT) analysis revealed that these absorption properties are mainly characterized by intramolecular charge transfer from the dibenzopyrromethene core to the thienyl-cyanoacrylic acid unit that depend on both the number of anchoring groups and the position of the thienyl-cyanoacrylic acid unit on the isoindole ring. The relationship between the chemical structures and cell properties of these dyes was investigated. Although the short circuit photocurrent density (J_sc) value of a 1-loaded cell is larger than that of a 3-loaded cell, which reflects the results of the incident photon-to-charge carrier efficiency (IPCE) spectra, the 1-loaded cell has a lower open circuit voltage (V_oc) and fill factor (FF). Accordingly, overall power-to-current conversion efficiencies of 5.24 and 5.48% were obtained for a 1-loaded cell and 3-loaded cell, respectively, under 100 mW cm⁻² AM1.5G simulated light. On the other hand, the cell containing butterfly-shaped regioisomer 2, which showed improved intramolecular charge transfer, has an overall power-to-current conversion efficiency of 6.06%; this value is the highest published for BODIPY dyes even though the sensitizer does not contain any strong donor units, such as arylamines.