Application of a novel copper ion colorimetric probe in experimental teaching
[Objective]The synthesis,characterization,and rapid detection of copper ions using colorimetric probe H-6 is part of a comprehensive chemistry experimental project that brings scientific research into undergraduate teaching.Copper,as an essential trace element in the human body,is crucial for various physiological activities.Traditional methods for detecting metal ions have drawbacks such as complexity,poor timeliness,low detection limits,and high costs.By contrast,molecular probes offer significant advantages in detecting metal ions.This full-process teaching approach,which includes a series of chemical characterization testing methods,aims to comprehensively develop students'skills,enhance their experimental abilities and scientific research literacy,and stimulate their innovative thinking.The experiment integrates multiple disciplines,such as organic chemistry,inorganic analysis,materials science,and instrumental analysis,enhancing the systematic and applied nature of experimental teaching.By integrating new colorimetric probe detection methods into undergraduate experimental teaching,the project aims to improve the quality of chemical talent cultivation.[Methods]Based on the structure of isophorone,an unreported target molecular probe,H-6,was designed and synthesized.The synthesis process involved the condensation of dicyano isophorone with p-hydroxybenzaldehyde aldehyde,adding an aldehyde group through the Duff reaction,and then condensing it with p-toluenesulfonyl hydrazine to generate the target product.A series of characterizations were conducted to determine the structure of probe H-6,including molecular design,organic synthesis,infrared spectroscopy,nuclear magnetic resonance(NMR)spectroscopy,mass spectrometry,density functional theory(DFT)calculations,and ultraviolet(UV)characteristic analysis.The spectral properties of the probe were studied to understand its specific detection of Cu2+ions.These studies included UV selectivity,competitiveness,concentration titration,and reversibility.Finally,the binding mechanism between Cu2+and probe H-6 was determined through Job's plot,high-resolution mass spectroscopy,nuclear magnetic titration,and other methods and further verified by comparing the gap energy before and after binding through DFT calculations.[Results]:Probe H-6 was successfully synthesized through a simple synthesis route,and its structure was determined through characterizations.Students gained a deeper understanding of FT-IR,HRMS,1H NMR,13C NMR,and UV spectroscopic instruments through the synthesis of the probe.The novel colorimetric probe H-6 exhibited a clear experimental phenomenon when detecting Cu2+ions,helping students understand the complexation between metal ions and the probe.Students mastered qualitative and quantitative analysis methods for colorimetric probe technology,explored the complexation ratio between colorimetric probe H-6 and Cu2+,and applied the established analysis methods to real sample analysis and rapid detection fields.This method boasts many advantages,such as simplicity,speed,low detection limit,high sensitivity,strong portability,and real-time on-site performance.It was applied to teaching to achieve comprehensive cultivation of students'thinking,knowledge,and abilities.[Conclusion]The isophorone-based probe H-6 was synthesized using a simple synthetic route that could visually identify Cu2+through UV spectroscopy and color changes in the solution.Spectroscopic studies revealed that probe H-6 could detect Cu2+concentrations by the ratio of UV absorption intensity,with a detection limit as low as 7.19 × 108 M.
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