N-邻羟基萘甲酰胺基-N′-苯基硫脲的合成及其对阴离子的识别

Study on Synthesis and Anion Recognition of N-(Orthohydroxynaphthamido)-N′-Phenylthioureas

设计合成了3种N-邻羟基萘甲酰胺基-N′-苯基硫脲类化合物,通过核磁共振谱和质谱表征了其结构。应用吸收光谱和荧光光谱考察了在乙腈中其与F-、CH3CO2-、H2PO4-、HSO4-、Cl-和Br-等阴离子的相互作用。结果表明,该类主体分子与阴离子形成结合比为1∶1氢键配合物,通过改变萘环上酰基和羟基的相邻位置可调控识别作用的选择性,它们与阴离子作用分别在355、367nm和372nm出现最大吸收峰,荧光光谱显示它们对F-有突出的响应灵敏度,可选择性识别F-。

The N-（orthohydroxynaphthamido）-N′-phenylthioureas were designed and synthesized and their structure were characterized by 1HNMR and ESI-MS.Their interaction with anions such as F^-、CH3CO2^-、H2PO4^-、HSO4^-、Cl^- and Br^- in acetonitrile were investigated by absorption and fluorescence spectra.The hydrogen bonding of 1∶1 complexes were formed between receptors and anions.The selectivity of receptors to anion could be efficiently tuned by altering substituent site of acyl and hydroxyl at N-naphtyl moiety.The receptors interaction with anions induced maximal new peaks at 355nm, 367nm and 372nm in the absorption spectra,respectively. The F^- induced enhancement of the receptors could be applied as selective fluorescent sensors for fluoride.