Synthesis and Comparative Kinetic Study of Reaction-Based Copper(II) Probes to Visualize Aromatic Substituent Effects on Reactivity

Abstract

Recently, researchers have paid extensive attention to colorimetric/fluorimetric probe development and its applications in biological and industrial samples. The actual development of such probe molecules, however, often requires an iterative process to achieve certain goals such as selectivity and sensitivity toward a target analyte. In spite of growing interest in the development of practical molecular probes, there has not been much effort to implement the synthesis of detector molecules and the examination of their structure–reactivity relationship in undergraduate laboratories. A straightforward synthesis of copper probe molecules, which are systematically varied with aromatic substituents, is described to compare the reactivity toward copper­(II) ion. The comparative kinetic study can readily visualize how the number and position of aromatic substituents affect the reactivity. This experiment is appropriate to demonstrate how mechanistic understanding will provide significant insight into rational design of practical colorimetric/fluorimetric probe molecules.

Small-molecule fluorescent probes based on covalent assembly strategy for chemoselective bioimaging

“…6C). [44][45][46][47][48][49][50][51][52][53][54] These probes demonstrated better water solubility, better selectivity, better biocompatibility, higher sensitivity through structural modication, and were applied in cell imaging or paper-based detection devices.…”

A Fluorometer-Free Experimental Course for Fluorescence Analysis Based on Smartphone and Image/Data-Processing Software Using a Synthetic Sensor

“…Several courses have been developed to enhance students' understanding of fluorescence analysis and have shown significant results. 10,11 However, a fluorometer is generally required to measure the value of fluorescence intensity, which poses certain challenges in undergraduate teaching. First, the equipment is expensive, and many undergraduates do not have access to it or cannot operate it individually.…”

“…Quantitative sensing technologies play an essential role in scientific research and modern chemical analysis. − Among these technologies, fluorescence analysis is characterized by high sensitivity and great simplicity, making it widely used for the quantification of heavy metal ions, warfare agents, biomolecules, etc. − Their fluorescence intensity increases or decreases after reaction with the target analyte, thus allowing us to obtain the concentration of target analyte by calculating the variation of fluorescence intensity. Several courses have been developed to enhance students’ understanding of fluorescence analysis and have shown significant results. , However, a fluorometer is generally required to measure the value of fluorescence intensity, which poses certain challenges in undergraduate teaching. First, the equipment is expensive, and many undergraduates do not have access to it or cannot operate it individually.…”

The detection of multiple analytes by using visual colorimetric and fluorometric multimodal chemosensor based on the azo dye

“…These dyes have advantages that include their low cost as industrial colorants, their simple synthesis, and the rich colours they produce [ 12 ]. Ortho-substituted azobenzenes, a subgroup of classical azo dyes, can distinguish Cu 2+ through reversible coordination reaction and through irreversible oxidation process [ 13 , 14 , 15 , 16 , 17 , 18 ]. In the development of chemosensors belonging to the ortho-amino azobenzene family, three different strategies have been applied.…”