Sobhani Leila, Darabi Hossein Reza, Atasbili Leila, Aghapoor Kioumars, Rastgar Saeed, Jadidi Khosrow, Naderi Soheila
Nano & Organic Synthesis Lab, Chemistry & Chemical Engineering Research Center of Iran, Tehran, Iran.
Department of Organic Chemistry, Shahid Beheshti University, Tehran, 1983969411, Iran.
J Fluoresc. 2025 Mar;35(3):1359-1372. doi: 10.1007/s10895-024-03596-x. Epub 2024 Feb 7.
Three novel acetalophanes 1a-c have been designed, synthesized and characterized. The receptors 1b-c, featuring bulky anthracene groups, displayed significant selectivity for Fe ions, resulting in a turn-off fluorescence mode in a DMF-buffer solution. Conversely, the non-steric probe 1a could serve as a versatile sensor for the simultaneous detection of Fe and Cu ions in MeOH-buffer solution. The sensing mechanism for the capability of 1a was demonstrated to be different, as evidenced by the addition of cyanide ions. The probes with Fe exhibited a sensing mechanism that resulted in the deprotection of acetals to the corresponding starting materials, as confirmed by H NMR, IR spectra and TLC analysis. The attractive features of these practical and efficient sensors are selectivity, sensitivity (limit of detection = 0.15 µM by 1a, 0.16 µM by 1b and 0.14 µM by 1c), rapid response (less than 5 s). The on-site monitoring of various real samples, including well water, apricot, and green tea, proved to be successful for the quantitative and cost-effective detection of Fe. The method demonstrated good precision, even in the presence of other interfering materials.
设计、合成并表征了三种新型缩醛洛芬1a - c。具有庞大蒽基的受体1b - c对铁离子表现出显著的选择性,在DMF - 缓冲溶液中导致荧光猝灭模式。相反,非空间探针1a可以作为一种通用传感器,用于在甲醇 - 缓冲溶液中同时检测铁离子和铜离子。通过添加氰化物离子证明,1a检测能力的传感机制有所不同。含有铁的探针表现出一种传感机制,通过1H NMR、红外光谱和薄层色谱分析证实,该机制导致缩醛脱保护为相应的起始原料。这些实用高效传感器的吸引人之处在于选择性、灵敏度(1a的检测限 = 0.15 μM,1b的检测限 = 0.16 μM,1c的检测限 = 0.14 μM)、快速响应(小于5秒)。对包括井水、杏子和绿茶在内的各种实际样品进行现场监测,证明对于铁的定量和经济高效检测是成功的。该方法即使在存在其他干扰物质的情况下也显示出良好的精密度。