Maiti Kalipada, Mahapatra Ajit Kumar, Gangopadhyay Ankita, Maji Rajkishor, Mondal Sanchita, Ali Syed Samim, Das Sujoy, Sarkar Ripon, Datta Pallab, Mandal Debasish
Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah 711103, India.
Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India.
ACS Omega. 2017 Apr 24;2(4):1583-1593. doi: 10.1021/acsomega.6b00288. eCollection 2017 Apr 30.
A bisthiocarbonohydrazone-based chemosensor molecule () containing a tetrahydro-8-hydroxyquinolizine-9-carboxaldehyde moiety has been synthesized and characterized as a new ratiometric fluorescent probe for picric acid (PA). The ratiometric probe is a highly selective and sensitive colorimetric chemosensor for PA. The association between the chemosensor and PA and the ratiometric performance enabled by the key role of excited state intramolecular proton transfer in the detection process are demonstrated. Selectivity experiments proved that has excellent selectivity to PA over other nitroaromatic chemicals. Importantly, the ratiometric probe exhibited a noteworthy change in both colorimetric and emission color, and this key feature enables to be employed for detection of PA by simple visual inspection in silica-gel-coated thin-layer chromatography plates. Probe has been shown to detect PA up to 3.2 nM at pH 7.4. Microstructural features of and its PA complex have been measured by a field emission scanning electron microscope, and it clearly proves that their morphological features differ dramatically both in shape and size. Density function theory and time-dependent density function theory calculations were performed to establish the sensing mechanism and the electronic properties of probe . Furthermore, we have demonstrated the utility of probe for the detection of PA in live Vero cells for ratiometric fluorescence imaging.
一种含有四氢-8-羟基喹啉嗪-9-甲醛部分的基于双硫代碳酰肼的化学传感器分子（）已被合成并表征为一种用于苦味酸（PA）的新型比率荧光探针。该比率探针是一种对PA具有高选择性和灵敏性的比色化学传感器。证明了化学传感器与PA之间的缔合以及激发态分子内质子转移在检测过程中的关键作用所实现的比率性能。选择性实验证明，与其他硝基芳烃化学品相比，对PA具有优异的选择性。重要的是，该比率探针在比色和发射颜色上都表现出显著变化，这一关键特性使得能够在硅胶涂层的薄层色谱板上通过简单的目视检查来检测PA。已证明探针在pH 7.4时能够检测高达3.2 nM的PA。通过场发射扫描电子显微镜测量了及其PA配合物的微观结构特征，清楚地证明了它们的形态特征在形状和大小上都有显著差异。进行了密度泛函理论和含时密度泛函理论计算，以建立探针的传感机制和电子性质。此外，我们已经证明了探针在活的Vero细胞中用于比率荧光成像检测PA的实用性。
