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Exploiting the unique specialty of hydrazone functionality: Synthesis of a highly sensitive UV–Vis active solvatochromic probe
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy ( IF 4.4 ) Pub Date : 2020-11-04 , DOI: 10.1016/j.saa.2020.119154
Mudeha Shafat Khan , Romana Khanam , Sajad Ahmad Bhat , Naheed Sidiq , Tabasum Ismail , Pravin P. Ingole , Rahul V. Pinjari , Mohsin Ahmad Bhat

The unique physico-chemical attributes of the hydrazone functionality have been extensively studied for a diverse range of chemical, biological and analytical applications. The synthesis of a highly sensitive hydrazone based UV–Vis active solvatochromic probe that exhibits excellent sensitivity toward sensing of solvent polarity, microstructural changes and onset of micellization in aqueous systems was carried out. Specifically, synthesis of 2,4-dinitrophenyl-2-(2-nitrobenzylidene)hydrazone (DNPNBH), through an easy to carry, atom economical, one-pot single step approach via use of low-cost precursors viz. ortho-nitrobenzaldehyde and 2,4-dinitrophenyl hydrazine is presented. The UV–Vis absorption features of the synthesized hydrazone exhibit excellent sensitivity toward the polarity of its immediate microenvironment. The microenvironment polarity sensing potential of DNPNBH is demonstrated for some single solvent systems and DMF-Water mixture as a model binary solvent system and the results are supported by quantum mechanical calculations. Use of the DNPNBH as a probe (at concentrations many orders lower than required for conventional probes) to precisely reflect the onset of micellization and estimation of critical micelle concentration (CMC) of amphiphilic molecules (5.25 mM for SDS, 1.53 mM for CTAB and 0.055 mM for Brij56) in aqueous solutions is also demonstrated. The results clearly qualify the synthesized hydrazone as a highly sensitive UV–Vis probe that can be employed for reliable sensing of solvent polarity, composition dependence of physicochemical attributes in mixed solvent systems and the estimation of CMC of surfactant systems via spectrophotometry.



中文翻译:

利用功能的独特优势:合成高灵敏度的UV-Vis活性溶剂化变色探针

functionality功能的独特物理化学属性已针对各种化学,生物学和分析应用进行了广泛研究。合成了一种高度敏感的UV基UV-Vis活性溶剂致变色探针,该探针对水体系中的溶剂极性,微结构变化和胶束化开始表现出出色的敏感性。具体地说,通过使用低成本前体的一种易于携带,原子经济,一锅法的单步合成方法来合成2,4-二硝基苯基-2-(2-硝基亚苄基)hydr(DNPNBH)。提出了邻硝基苯甲醛和2,4-二硝基苯基肼。合成的的UV-Vis吸收特征对其紧邻的微环境的极性显示出极好的敏感性。对于某些单一溶剂系统和DMF-水混合物作为模型二元溶剂系统,证明了DNPNBH的微环境极性传感潜力,并且该结果得到了量子力学计算的支持。使用DNPNBH作为探针(其浓度比常规探针所需的浓度低许多个数量级)以精确反映胶束化的发生和两亲分子的临界胶束浓度(CMC)的估算(SDS为5.25 mM,CTAB为1.53 mM,0.055水溶液中的Brij56的mM也已证明。结果清楚地证明了合成的as为高度敏感的UV-Vis探针,可用于可靠地检测溶剂极性,

更新日期:2020-11-12
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