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Multifunctional behavior of bis-acylhydrazone: Real-time detection of moisture in organic solvents, halochromism and aggregation induced emission
Dyes and Pigments ( IF 4.1 ) Pub Date : 2020-10-06 , DOI: 10.1016/j.dyepig.2020.108891
Kuppusamy Santhiya , Shovan K. Sen , Ramalingam Natarajan , Balasubramanian Murugesapandian

A versatile novel indenopyrazine/indenoquinoxaline appended acylhydrazones (1 and 2) have been designed and synthesized successfully. Compounds 1 and 2 are designed such that, it comprises of acylhydrazone, which is responsible for moisture detection via deprotonation of the original molecule, pyrazine, pyridine and hydrazone unit which is responsible for halochromism via protonation and deprotonation, further the integrated twisted molecular structure results in the aggregation-induced emission features. Successive treatment of Fˉ and moisture to compound 1 and 2 produce reversible colorimetric responses that are easily visualized by the naked eye. Further, the corresponding mechanism was effectively confirmed by 1H NMR spectral analysis. The inherent halochromic features of appended unique pyrazine and pyridine core in compounds 1 and 2 were studied by the sequential addition of trifluoroacetic acid (TFA) and triethylamine (TEA) which is authenticated by reversible colorimetric changes as well as absorption spectral studies. Compound 1 adopts a twisted scissor-like structure and due to multiple weak interactions results in an interesting supramolecular network. Furthermore, both compound 1 and 2 exhibits the aggregation-induced emission features in DMF/water mixture, which was expansively confirmed through DLS particle analysis and TEM images. The integration of three distinct features into a single molecule are scarce.



中文翻译:

双酰基hydr的多功能行为:实时检测有机溶剂中的水分,色变和聚集诱导的发射

已成功设计并合成了一种新型的新型茚并吡嗪/茚并喹喔啉附加酰基hydr(12)。对化合物12进行设计,使其包含酰基zone和吡,、吡啶和unit单元,酰基hydr通过原始分子的去质子化来进行水分检测,吡嗪,吡啶和单元通过质子化和去质子化来产生卤致变色现象,进而获得完整的扭曲分子结构结果在聚集引起的排放特征。连续处理F 1和水分至化合物12产生可逆的色度响应,用肉眼即可轻松看到。此外,通过1 H NMR光谱分析有效地确认了相应的机理。通过依次添加三氟乙酸(TFA)和三乙胺(TEA)来研究在化合物12中附加的独特吡嗪和吡啶核的固有盐变色特征,该特征已通过可逆比色法变化和吸收光谱研究进行了验证。化合物1采用扭曲的剪刀状结构,由于多重弱相互作用而形成了有趣的超分子网络。此外,化合物12在DMF /水混合物中具有聚集诱导的发射特征,这通过DLS颗粒分析和TEM图像得到了广泛证实。缺乏将三个不同特征整合到单个分子中的功能。

更新日期:2020-10-15
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