Pyridinium‐Based Schiff‐Base Fluorescent Chemosensor for Sequential Detection of Al3+ Ions and TNP: Applications in Cell Imaging and Latent Fingerprint Visualization

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI:10.1002/ajoc.202400669

Pragya , Sonali J. Jain , Krishnan Rangan , Prabhat Nath Jha , Bharti Khungar

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Abstract

A fluorescent pyridinium‐based chemosensor (E)‐1‐(2‐(3‐hydroxy‐4‐((pyridin‐2‐ylimino) methyl) phenoxy) ethyl) pyridin‐1‐ium bromide (BzPySB) was synthesized and characterized using various spectroscopic techniques. The chemosensing potential of BzPySB was explored using UV‐vis and fluorescence spectroscopy in the aqueous medium. The turn‐on fluorescence behavior was observed for BzPySB in the presence of Al³⁺, while other metal ions were non‐responsive. The B−H and Job′s plot confirmed the 1 : 1 stoichiometric ratio of the BzPySB and Al³⁺. The in situ generated complex BzPySB‐Al³⁺ offered selectivity toward TNP via fluorescence turn‐off phenomena with high K_sv and LOD values. The “off‐on‐off” sensing mechanism was elucidated through ¹H NMR, mass spectrometry, and DFT calculations. The probe also detected Al³⁺ in plant and MCF‐7 cells, highlighting its potential in biological systems. Moreover, BzPySB exhibited solid‐state luminescent properties credited to weak π‐π interaction, leading to its successful application in the visualization of latent fingerprints.

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本研究合成了一种基于吡啶的荧光化学传感器（E）-1-(2-(3-羟基-4-((吡啶-2-亚氨基)甲基)苯氧基)乙基)吡啶-1-鎓溴化物（BzPySB），并利用各种光谱技术对其进行了表征。在水介质中使用紫外可见光谱和荧光光谱探索了 BzPySB 的化学传感潜力。观察到 BzPySB 在 Al3+ 存在下的荧光开启行为，而其他金属离子则无反应。B-H 图和 Job′s 图证实了 BzPySB 和 Al3+ 的化学计量比为 1 ：1 的化学计量比。原位生成的 BzPySB-Al3+ 复合物通过荧光熄灭现象对 TNP 具有选择性，具有较高的 Ksv 值和 LOD 值。通过 1H NMR、质谱分析和 DFT 计算，阐明了 "off-on-off "传感机制。该探针还能在植物和 MCF-7 细胞中检测到 Al3+，突显了其在生物系统中的应用潜力。此外，由于 BzPySB 具有微弱的 π-π 相互作用，因此它具有固态发光特性，从而成功地应用于潜在指纹的可视化。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.