Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-11-07 , DOI: 10.1016/j.tetlet.2015.11.017 Anup Pandith , Ashwani Kumar , Ju-Young Lee , Hong-Seok Kim
A new class of ‘switch off’ anthracenecarboxamide-based sensing probes (1–3) for the detection of picric acid (PA) was designed and synthesized. Probe 1 exhibited the highest sensitivity and selectivity toward PA, enabling complete fluorescence quenching and exhibiting a high association constant (4.14 × 105 M−1) with a 1:1 stoichiometric ratio of 1 to PA in EtOH. Probe 1 was able to detect PA through multiple synergic interactions such as hydrogen bonding, π–π interactions between the electron-rich aromatic rings of anthracene and the electron-deficient aromatic ring of PA that resulted in a favorable fluorescence resonance energy transfer from the latter to the former. The ability of probe 1 to sense PA was investigated by UV–visible, fluorescence, and 1H NMR spectroscopies, as well as DFT calculations.
中文翻译:
9-蒽羧酰胺荧光探针,用于从乙醇中的单硝基酚和二硝基酚选择性鉴别苦味酸
一类新的“的关闭”基于anthracenecarboxamide传感探头(1 - 3)用于检测苦味酸(PA)的设计和合成。探针1对PA表现出最高的灵敏度和选择性,能够实现完全的荧光淬灭,并在EtOH中以1与PA的化学计量比为1:1的方式具有高缔合常数(4.14×10 5 M -1)。探针1能够通过多种协同相互作用(例如氢键,π – π)检测PA蒽的富电子芳环与PA的缺电子芳环之间的相互作用,导致了从后者到前者的良好荧光共振能量转移。通过紫外可见光,荧光和1 H NMR光谱以及DFT计算,研究了探针1感测PA的能力。