Rapid Turn-On Fluorescence Detection of Copper(II): Aromatic Substituent Effects on the Response Rate

Abstract

Oxidative cyclization of o-phenylazo aniline was utilized as a turn-on fluorescent probe of the copper(II) ion. The number and the position of electron donating groups on the probes were systematically varied to investigate the effect of aryl substituent on reactivity toward copper ion. Among the series of analogous probes, the 2,4,6-trimethoxy substituted probe exhibits not only a faster (40-times faster) reaction but also a lower detection limit (20 times lower) than previously reported probes under identical conditions. The comparative kinetic studies reveal that both the number and the position of substitution have a significant impact on the reactivity toward copper, which will be discussed in the manuscript.

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.…”

P1AP.11 - Online Copper Monitoring for Pharmaceutical Processes

“…Due to its toxicity health regulatory agencies such as FDA strictly regulated the residual amount of copper in the final drug products [2]. Oxidative cyclization of ortho-azo anilines has been used to detect low level of copper (II) ion [3,4]. We prepared a series of copper probe molecules which were systematically varied with electron donation groups.…”

Computational investigation of the substituent effect in the [2 + 4] Diels–Alder cycloaddition reactions of HSi≡Si(para‐C6H4X) with benzene

“…Variations in the electron‐donating groups (EDGs) and electron‐withdrawing groups (EWGs) of molecules are effective on different physical and chemical properties. Computational investigations of substituent effects on the structure and properties of the molecules have been reported 39–68 …”