Dynamic Chemistry-Based Sensing: A Molecular System for Detection of Saccharide, Formaldehyde, and the Silver Ion

Abstract

Development of artificial complex molecular systems is of great importance in understanding complexity in natural processes and for achieving new functionalities. One of the strategies is to create them via optimized utilization of noncovalent interactions and dynamic covalent bonds. We report here on a new complex molecular system, which was constructed by integrating the multiple interactions containing a dynamic covalent interaction between 1,2-diol and boronic acid, a coordination interaction between the silver ion and pyridyl, and an easy accessible reaction between secondary amine and formaldehyde. By employing the three dynamic interactions, a pyrene (Py) labeled fluorophore, PPB, was designed and synthesized. The compound reacts with fructose (F), a monosaccharide, in aqueous phase and produces a fluorescent adduct, PPB-F, which can be further used as a sensing platform for formaldehyde (FA) and the silver ion. The respective dynamic interactions are accompanied with color changes due to the reversible switching between Py-monomer emission and excimer emission. The respective experimental detection limits (DLs) for the three analytes are much lower than 0.2 mM, 0.1 mM, and 2.5 μM, respectively. The presence of relevant compounds or ions shows little effect upon the sensing. No doubt, the results as presented show that the integration of supramolecular interactions including dynamic covalent bonds can be employed as a general strategy to develop new functional molecular systems or materials.

Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials

“…For example, guest-triggered transformation within dynamic combinatorial libraries was targeted for chemical sensing . A variety of arylboronic acid derived fluorescence receptors were developed for reversible covalent bonding and detection of saccharides . Moreover, aggregation induced emission active tetraphenylethene motifs were integrated into dynamic covalent assemblies toward emissive systems in solution or solid state .…”

Rapid Analysis of Monosaccharides in Sub-milligram Plant Samples Using Liquid Chromatography–Mass Spectrometry Assisted by Post-column Derivatization

“…For the rapid analysis of monosaccharides by LC–PCD–MS, a derivatization reagent that satisfies the requirements of PCD is required. Boronic acid reagents have been widely used to label cis -diols. − In our previous study, 4-PAMBA has been used as the derivatization reagent for the highly sensitive detection of brassinosteroids (BRs). , However, the derivatization products of boronic acid reagents with cis -diol compounds, such as monosaccharides, are easily decomposed during LC separation . Therefore, pre-column derivatization is not suitable for the determination of monosaccharides by LC–MS using 4-PAMBA as the derivatization reagent.…”

“…The reaction solvent must be compatible with the LC mobile phase, and the reaction must be fast under mild conditions, such as at room temperature. It is well-known that boronic acid reagents have been widely applied for the detection of sugar by biosensors. − Besides, the reactions between boronic acid reagents and cis -diols are rapid and highly selective under mild reaction conditions. , Therefore, we speculated that boronic acid reagents are ideal derivatization reagents for the analysis of monosaccharides by LC–PCD–MS.…”

Self-Healable and Recyclable Dynamic Covalent Networks Based on Room Temperature Exchangeable Hydrazide Michael Adduct Linkages

“…This autonomously exchangeable covalent chemistry offers a distinct advantage over a range of conventional dynamic covalent linkages those typically require catalyst or external stimuli in form of heat or light energy to exhibit dynamic behavior. The fast exchange dynamics of covalent linkages have already shown promise in areas of controlled release, 3D cell encapsulation, biomedical implants, sensing, and energy storage applications . The swift exchangeability of reported dynamic hydrazide Michael adducts may be utilized in future for similar applications.…”