Wang Jing, Zong Zi-Ao, Huang Shi-Fu, Muddassir Mohd, Xing Zhi-Yong, Li Na-Na, Jiang Wen-Qiong
Modern Industrial College of Biomedicine and Great Health, Youjiang Medical University for Nationalities, Baise, 533000, China.
Key Laboratory of Research on Environment and Population Health in aluminium mining areas (Youjiang, Medical University for Nationalities), Education Department of Guangxi Zhuang Autonomous Region, Baise, China.
J Fluoresc. 2025 May 16. doi: 10.1007/s10895-025-04296-w.
In this work, an easy prepared solid fluorescent sensor 3-(benzo[d]thiazol-2-yl)-1-hydroxy-4-oxo-3,4-dihydrophthalazine-6-carboxylic acid (BPCA) was designed and synthesized and the structure was proved by IR, UV-Vis, NMR, HRMS and elemental analysis, which displayed high selectivity and sensitivity for fluorescence colormetric from green to blue sensing 1, 4-dioxane in water, and the detection limit was obtained 0.009% and the stability constant was 7.4 × 10 M. Also, sensor BPCA was applied for the real-time monitoring 1, 4-dioxane vapor with apparent fluorescent color change from green to blue. The mild and specific chemical interaction between sensor BPCA and 1, 4-dioxane molecule allowed the sensor as portable chips to respond 1, 4-dioxane vapor with good selectivity over other common VOCs at room temperature. Also, the sensing mechanism based on the 1, 4-dioxane-induced keto-enol tautomerization of the phthalazine moiety was found and supported by DFT calculations. This sensor could serve as the basis of gas analyzers for detecting 1, 4-dioxane in the environment.
在本工作中，设计并合成了一种易于制备的固体荧光传感器3-(苯并[d]噻唑-2-基)-1-羟基-4-氧代-3,4-二氢酞嗪-6-羧酸（BPCA），其结构通过红外光谱、紫外可见光谱、核磁共振、高分辨质谱和元素分析得以证实。该传感器对水中1,4-二氧六环的荧光比色检测显示出高选择性和灵敏度，检测限为0.009%，稳定常数为7.4×10 M。此外，传感器BPCA用于实时监测1,4-二氧六环蒸汽，荧光颜色明显从绿色变为蓝色。传感器BPCA与1,4-二氧六环分子之间温和且特异的化学相互作用使得该传感器作为便携式芯片在室温下对1,4-二氧六环蒸汽具有良好的选择性，优于其他常见挥发性有机化合物。同时，基于1,4-二氧六环诱导的酞嗪部分酮-烯醇互变异构的传感机制被发现，并得到密度泛函理论计算的支持。该传感器可作为环境中检测1,4-二氧六环的气体分析仪的基础。
