Recognition and sensing of various species using boronic acid derivatives

Abstract

A boronic acid moiety can bind to nucleophilic species, such as fluoride ions and 1,2-diols, and arylboronates are converted to the corresponding phenols by treatment with hydrogen peroxide. Based on these reactivity profiles of boron compounds, a variety of boronic acid and boronate-based fluorescent chemosensors have been developed for detecting biologically relevant species. This feature article highlights recent advances that have been made in the development of chemosensors of these types for monitoring carbohydrates, dopamine, fluorides, metal ions and hydrogen peroxide.

Strongly Emissive and Photostable Four‐Coordinate Organoboron N,C Chelates and Their Use in Fluorescence Microscopy

“…The four-coordinate situation of the boron center confers increased stability against nucleophilic attack, contrasting the behavior of three-coordinate organoboron compounds. [28][29][30][31] The obtained results underpin an improved design of strongly fluorescent and electronically versatile organoboron N,C-chelates and suggest their use in the fluorescence imaging of biological structures. …”

“…In order to underpin the strong charge-transfer character of the fluorescence of dye 4 an extended series of nine solvents was investigated ( Figure 4). As shown in Figure 5, the spectral position of the fluorescence maximum can be correlated with the orientation polarizability (f) and also with empirical solvent parameters such as the Dimroth-Reichardt parameter [ET (30)]. [39,40] Furthermore, a Lippert-Mataga plot [41][42][43] ( In the cases of the ICT dyes 2-4 the fluorescence quantum yields reach values as high as 0.5-0.6 in air-equilibrated toluene solution and also in more polar solvents (see Table 1).…”

Molecular recognition with boronic acids—applications in chemical biology

“…This is the basis of a number of receptors for fluoride, cyanide and phosphate anions. The reactivity of boronic acids and their use as anion sensors have been covered recently in reviews by Nishiyabu et al [55], Wade et al [75] and Guo et al [26] (Fig. 2).…”

Development of Supramolecular Saccharide Sensors Based on Cyclodextrin Complexes and Self-assembling Systems

“…In this regard, synthetic chemical receptors have attracted much attention for possible analytical and therapeutic applications. 8,9) Phenylboronic acids are known to form reversible covalent bonds with cis-1,2-and cis-1,3-diol-containing biomolecules, 10,11) such as saccharides and glycoproteins, forming five-and six-membered cyclic boronic esters, respectively, that are stable in alkaline aqueous solution and dissociate at acidic pH 12) (Fig. 1).…”