A novel DHP-NH2 fluorescent dye for the determination of water content in organic solvents, rice, and aspirin: DFT calculations

Sensors International Pub Date : 2025-08-09 DOI:10.1016/j.sintl.2025.100349

Kittiporn Nakprasit , Panyakorn Taweechat , Pornthep Sompornpisut , Mongkol Sukwattanasinitt , Waroton Paisuwan , Anawat Ajavakom

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Abstract

A novel aminodihydropyridine derivative (DHP-NH₂) was synthesized from hydrazine via a tandem cyclotrimerization of methyl propiolate. DHP-NH₂ distinguishably exhibited either strong fluorescence in aprotic solvents or weak fluorescence in protic solvents. Its fluorescence quenching in THF and MeCN was quantitatively determined in the presence of water content, demonstrating the limit of detection (LOD) of 0.036 %wt and 0.014 %wt in THF and MeCN, respectively. The critical hydrogen-bonding interactions between water molecules and the amino group of DHP-NH₂ were found to stabilize its excited state, supporting a quenching mechanism as confirmed by DFT/TDDFT calculations. To apply this DHP-NH₂ probe for on-site analysis, smartphone-based photography together with the ImageJ program was employed for the moisture detection with the LOD of 0.28 %wt in MeCN. Moreover, the trace amount of moisture in organic solvents and solid samples (rice and aspirin) was successfully detected by using this developed method. In addition, we successfully immobilized the DHP derivative onto the cellulose paper to be used as a portable test strip for determining water content in MeCN by naked-eye detection.

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一种新型DHP-NH2荧光染料，用于测定有机溶剂、大米和阿司匹林中的水分含量：DFT计算

以丙酸甲酯为原料，通过串联环三聚化反应合成了一种新的氨基二氢吡啶衍生物（DHP-NH2）。DHP-NH2在非质子溶剂中表现出强荧光，在质子溶剂中表现出弱荧光。在有水存在的情况下，定量测定了其在THF和MeCN中的荧光猝灭，其在THF和MeCN中的检出限（LOD）分别为0.036% wt和0.014% wt。发现水分子与DHP-NH2氨基之间的临界氢键相互作用稳定了其激发态，支持DFT/TDDFT计算证实的猝灭机制。为了将该DHP-NH2探针应用于现场分析，采用智能手机摄影结合ImageJ程序对men中的水分进行检测，LOD为0.28% wt。此外，该方法还成功地检测了有机溶剂和固体样品（大米和阿司匹林）中的微量水分。此外，我们成功地将DHP衍生物固定在纤维素纸上，作为裸眼检测MeCN含水量的便携式试纸条。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Sensors International

CiteScore

17.40

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0.00%

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