Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India.
Chemistry. 2012 Nov 12;18(46):14745-51. doi: 10.1002/chem.201201764. Epub 2012 Sep 27.
Herein we report a novel fluoranthene-based fluorescent fluorophore 7,10-bis(4-bromophenyl)-8,9-bis[4-(hexyloxy)phenyl]fluoranthene (S(3)) and its remarkable properties in applications of explosive detection. The sensitivity towards the detection of nitroaromatics (NACs) was evaluated through fluorescence quenching in solution, vapor, and contact mode approaches. The contact mode approach using thin-layer silica chromatographic plates exhibited a femtogram (1.15 fg cm(-2)) detection limit for trinitrotoluene (TNT) and picric acid (PA), whereas the solution-phase quenching showed PA detection at the 2-20 ppb level. Fluorescence lifetime measurements revealed that the quenching is static in nature and the quenching process is fully reversible. Binding energies between model binding sites of the S(3) and analyte compounds reveal that analyte molecules enter into the cavity created by substituted phenyl rings of fluoranthene and are stabilized by strong intermolecular interactions with alkyl chains. It is anticipated that the sensor S(3) could be a promising material for the construction of portable optical devices for the detection of onsite explosive nitroaromatics.
在此，我们报告了一种新型基于荧蒽的荧光荧光团 7,10-双(4-溴苯基)-8,9-双[4-(己氧基)苯基]荧蒽(S(3))，及其在爆炸物检测应用中的显著性质。通过溶液、蒸气和接触模式方法中的荧光猝灭来评估其对硝基芳烃(NACs)检测的灵敏度。使用薄层硅胶色谱板的接触模式方法对三硝基甲苯(TNT)和苦味酸(PA)的检测限达到飞克级(1.15 fg cm(-2))，而溶液相猝灭则显示 PA 在 2-20 ppb 水平下的检测。荧光寿命测量表明猝灭是静态的，且猝灭过程是完全可逆的。S(3)的模型结合位点与分析物化合物之间的结合能表明，分析物分子进入由荧蒽取代苯基环形成的腔中，并通过与烷基链的强分子间相互作用而稳定。预计传感器 S(3)可能成为构建用于现场检测爆炸物硝基芳烃的便携式光学设备的有前途的材料。
