9-Anthracenecarboxamide fluorescent probes for selective discrimination of picric acid from mono- and di-nitrophenols in ethanol

被引：39

作者：

Pandith, Anup ^{[1
]}

Kumar, Ashwani ^{[1
]}

Lee, Ju-Young ^{[1
]}

Kim, Hong-Seok ^{[1
]}

机构：

[1] Kyungpook Natl Univ, Sch Appl Chem Engn, Dept Appl Chem, Taegu 702701, South Korea

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 51期

基金：

新加坡国家研究基金会;

关键词：

9-Anthracenecarboxamide; Picric acid; Multiple hydrogen bonding; Energy transfer; Switch-off; QUANTUM YIELD; ANTHRACENE; PYRENE; SENSORS; CHEMOSENSOR; EXPLOSIVES; DERIVATIVES; STACKING;

D O I：

10.1016/j.tetlet.2015.11.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of 'switch off' antbracenecarboxamide-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 x 10(5) 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, pi-pi 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 H-1 NMR spectroscopies, as well as DFT calculations. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：7094 / 7099

页数：6