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2-吡喃-2-酮官能化的二酮吡咯并吡咯染料:设计、合成与爆炸物传感器

2-Pyran-2-one-Functionalized Diketopyrrolopyrrole Dye: Design, Synthesis, and Explosives Sensor.

作者信息

More Kerba S, Mirgane Harshad A, Shaikh Salman, Perupogu Vijayanand, Birajdar Shailesh S, Puyad Avinash L, Bhosale Sidhanath V, Bhosale Sheshanath V

机构信息

School of Chemical Sciences, Goa University, Taleigao Plateau 403206, Goa, India.

School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Nanded 431606, Maharashtra, India.

出版信息

J Org Chem. 2024 May 3;89(9):5917-5926. doi: 10.1021/acs.joc.2c01439. Epub 2022 Dec 19.

Abstract

In this work, a 2-pyran-2-one-functionalized diketopyrrolopyrrole (DPP) (coded as receptor ) was designed, synthesized, and fully characterized by various spectroscopic methods. The physical properties of molecular architecture were studied employing theoretical calculations. Receptor was elegantly scrutinized for the sensing of explosive nitroaromatic compounds (NACs). Receptor exhibited detection of nitro explosives, i.e., picric acid (PA), 2,4-dinitrophenol (DNP), and nitrophenol (NP), the fluorescence quenching mechanism. The Stern-Volmer equation was employed to evaluate the effectiveness of the quenching process. It was found that exhibited a detection limit of about 7.58 × 10, 8.35 × 10, and 9.05 × 10 M toward PA, DNP, and NP, respectively. The influence of interfering metal ions and anions on PA detection was investigated thoroughly. Furthermore, receptor based low-cost fluorescent thin-layer chromatography (TLC) plates were developed for the recognition of PA.

摘要

在本工作中,设计、合成了一种2-吡喃-2-酮官能化的二酮吡咯并吡咯(DPP)(编码为受体),并通过各种光谱方法对其进行了全面表征。采用理论计算研究了分子结构的物理性质。对受体检测爆炸性硝基芳香族化合物(NACs)的性能进行了精细研究。受体对硝基炸药,即苦味酸(PA)、2,4-二硝基苯酚(DNP)和硝基苯酚(NP)有检测效果,并呈现荧光猝灭机制。采用斯特恩-沃尔默方程评估猝灭过程的有效性。结果发现,受体对PA、DNP和NP的检测限分别约为7.58×10⁻⁸、8.35×10⁻⁸和9.05×1⁻⁸ M。深入研究了干扰金属离子和阴离子对PA检测的影响。此外,还开发了基于受体的低成本荧光薄层色谱(TLC)板用于PA的识别。

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