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首页> 外文期刊>RSC Advances >Imidazole-appended 9,10-anthracenedicarboxamide probe for sensing nitrophenols and selective determination of 2,4,6-trinitrophenol in an EtOH–water medium
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Imidazole-appended 9,10-anthracenedicarboxamide probe for sensing nitrophenols and selective determination of 2,4,6-trinitrophenol in an EtOH–water medium

机译：咪唑 - 所附9,10-蒽丙烯酰胺探针，用于检测硝基苯酚和2,4,6-三硝基苯酚在EtOH-水介质中的选择性测定

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摘要

A novel imidazole-appended anthracenedicarboxamide “switch-off” probe, AIM-D , was designed and synthesized for nitrophenol sensing. AIM-D selectively detected 2,4,6-trinitrophenol (TNP) relative to other nitrophenol derivatives through a ratiometric fluorescence response in 1?:?1 EtOH–H _(2) O and exhibited a large Stern–Volmer quenching constant ( K _(sv) = 2.69 × 10 ~(7) M ~(?1) ) and a binding ratio of 1?:?2. Mono- and dinitrophenols also quenched anthracene emission to a moderate (～37%) or great (～80%) extent depending on the position(s) of the nitro group(s) on the aromatic ring. The limit of detection of TNP with AIM-D was 1 ppb. The selective ratiometric discrimination of TNP over other nitrophenols was attributed mainly to protonation-induced electron transfer aided synergistic coulombic, multiple hydrogen bonding and π _(an) –π _(TNP) interactions in a symmetrical manner. Monomer quenching resulted from resonance energy transfer and a new enhancement at 520 nm occurred as a result of the effective inhibition of intramolecular charge transfer through intermolecular sequential opposite charge flow between AIM-D and TNP. However, mono- and dinitrophenol sensing attributed to the nitro group oriented resonance energy transfer from the latter to the former without inducing protonation at imidazole resulted in only monomer band quenching. An AIM-D coated paper strip was applied to the detection of nitrophenols in sea and river water samples and showed a limit of detection of 20 nM. The interaction of AIM-D with nitrophenols was examined by UV-visible, fluorescence, and ~(1) H NMR spectrometry and supported by DFT calculations.
机译：设计和合成了一种新型咪唑依次含有蒽酰胺羧酰胺“关断”探针，AIM-D用于硝基苯酚感测。 AIM-D通过1的比例荧光反应选择性地检测2,4,6-三硝基苯酚（TNP），在1？：1 EtOH-H _（2）O中，并显示出大型船尾淬火常数（k _（SV）= 2.69×10〜（7）m〜（α1））和1的结合率为1？：？2。单滴度和二硝基酚还根据芳香环上的硝基组的位置淬灭蒽（〜37％）或大（〜80％）范围。用AIM-D检测TNP的极限为1 ppb。 TNP在其他硝基苯酚上的选择性比率鉴定主要是质子化诱导的电子转移辅助协同作用库仑，多氢键合和π_（AN）-π_（TNP）相互作用以对称的方式。单体淬火由共振能量转移产生，并且由于在AIM-D和TNP之间的分子间顺序相反电荷流动的分子内电荷转移的有效抑制而发生了520nm的新增增强。然而，单硝基苯酚感测归因于硝基基团取向从后者到前者的谐振能量转移，而不诱导咪唑的质子化导致单体带猝灭导致。 AIM-D涂布纸条用于检测海洋和河流水样中的硝基苯酚，并显示出20nm的检测限。通过UV可见，荧光和〜（1）H NMR光谱法检测AIM-D与硝基苯酚的相互作用，并通过DFT计算支持。

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