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基于双酚的氰化物传感:选择性、可逆性、简便合成、双侧“关-开”荧光、C 结构和构象分析。

Bisphenol-based cyanide sensing: Selectivity, reversibility, facile synthesis, bilateral "OFF-ON" fluorescence, C structural and conformational analysis.

机构信息

Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea; Graduate School of Energy, Environment, Water and Sustainability (EEWS), KAIST, 291 Daehak-ro, Yuseong-gu, Daejeon 34141, Republic of Korea.

Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, Republic of Korea.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2021 Oct 5;259:119881. doi: 10.1016/j.saa.2021.119881. Epub 2021 Apr 26.

DOI:10.1016/j.saa.2021.119881
PMID:33971439
Abstract

A structurally characterized novel dual-pocketed tetra-conjugated bisphenol-based chromophore (fluorescence = 652 nm) was synthesized in gram scale in ~90% yield from its tetraaldehyde. Highly selective, naked-eye detection of CN (DMSO/HO) was confirmed by interferent testing. A detection limit of 0.38 µM, within the permissible limit of CN concentration in drinking water was achieved as mandated by WHO. The "reversibility" study shows potential applicability and reusability of Sen. Moreover, cost-effective and on-site interfaces, application tools such as fabricated cotton swabs, plastic Petri dishes, and filter papers further demonstrated the specific selectivity of Sen for the toxic CN. In addition, an easily available and handy smartphone-assisted "Color Picker" app was utilized to help estimate the concentration of CN ion present. A dual phenol deprotonation mechanism is active and supported by H NMR spectroscopic data and DFT calculation results.

摘要

一种结构特征明确的新型双口袋四共轭双酚基发色团(荧光=652nm),以其四醛为原料,在克级规模下以~90%的收率合成。通过干扰测试,证实了对 CN(DMSO/HO)的高度选择性、肉眼检测。检测限为 0.38µM,符合世界卫生组织规定的饮用水中 CN 浓度的允许限值。“可逆性”研究表明,Sen 具有潜在的适用性和可重复使用性。此外,经济高效且现场接口、制造棉签、塑料培养皿和滤纸等应用工具进一步证明了 Sen 对有毒 CN 的特殊选择性。此外,还利用易于获取的智能手机辅助“颜色选择器”应用程序来帮助估计存在的 CN 离子浓度。双酚去质子化机制是活跃的,并得到 H NMR 光谱数据和 DFT 计算结果的支持。

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