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A series of novel 1H-indole-7-carbohydrazide derivatives with photoswitching and AIE properties: “On-off” fluorescence sensors for Cu2+
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2023-08-16 , DOI: 10.1016/j.molstruc.2023.136433
Haoran Hu , Junqi Li , Lei Shi , Tongtong Jing , Chong Zhang , Chao Gao , Chengguo Sun , Yang Du , Bingcheng Hu

In order to exploit novel fluorescent sensors with photoswitching properties, six fluorescent molecules were synthesized via coupling 1H-indole-7-carbohydrazide and corresponding substituted formaldehyde through an acylhydrazone bond. All title compounds were characterized via 1H, 13C NMR, and elemental analysis, the single crystal structure of compound IC-PD was obtained via X-ray diffraction. The compounds IC-EL and IC-4PZ exhibited aggregation-induced emission (AIE) characteristics and also with regular responses to temperature and alkalinity in the solvent system dominated via deionized water. Probes IC-PL, IC-4PZ, and IC-PD could be used as fluorescence probes to detect copper (Ⅱ) with the LODs of 0.37, 0.27, and 0.26 μM in concentration of 0–50 μM, especially extraordinary bits of complex IC-PD-Cu2+ could also exhibited bright yellow in tetrahydrofuran (THF), which ensured the convenience of detection for Cu2+ ion. The exploration on the combination mechanism of representative compound IC-PD and Cu2+ ion via FT-IR and 1H NMR, which confirmed that the proton of hydrazide was protonated via Cu2+ ion, resulting in the excited state intramolecular proton transfer (ESIPT) process was interfered. When IC-PD was irradiation to the 302 nm photostationary state (PSS), the fluorescence emission intensity of IC-PD in THF was slightly enhanced, accompanied with the increased sensitivity of detection for Cu2+. Although the improvement was not significant, it was also provided a design foundation for the development of stimuli responsive fluorescent materials with photoswitching properties.



中文翻译:

一系列具有光开关和 AIE 特性的新型 1H-吲哚-7-碳酰肼衍生物:Cu2+ 的“开关”荧光传感器

为了开发具有光开关特性的新型荧光传感器,通过酰腙键偶联1 H-吲哚-7-碳酰肼和相应的取代甲醛,合成了六种荧光分子。所有标题化合物均通过 1 H、13 C NMR 和元素分析进行​​表征,通过X 射线衍射获得了化合物IC-PD的单晶结构。化合物IC-ELIC-4PZ表现出聚集诱导发射 (AIE) 特性,并且对溶剂系统中的温度和碱度有规律的响应去离子水。探针IC-PL、IC-4PZIC-PD可作为荧光探针检测铜(Ⅱ),在0-50 μM浓度下LOD分别为0.37、0.27和0.26 μM,特别是复杂IC的特殊位点-PD -Cu 2+在四氢呋喃(THF)中也能呈现亮黄色,保证了Cu 2+离子检测的方便性。通过FT-IR和1 H NMR探索了代表性化合物IC-PD与Cu 2+离子的结合机理,证实酰肼的质子是通过Cu 2+质子化的离子,导致激发态分子内质子转移(ESIPT)过程受到干扰。当IC-PD受到302 nm光稳态(PSS)照射时,IC-PD在THF中的荧光发射强度略有增强,同时对Cu 2+的检测灵敏度增加。虽然改进并不显着,但也为开发具有光开关特性的刺激响应荧光材料提供了设计基础。

更新日期:2023-08-16
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