Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing.
Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing.
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DOI：
10.3390/ijms23052760
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发表时间：
2022-03-02
影响因子：
5.6
通讯作者：
Oancea F
中科院分区：
文献类型：
--
作者：
Tigoianu R;Airinei A;Georgescu E;Nicolescu A;Georgescu F;Isac DL;Deleanu C;Oancea F
合成了以哌啶取代的1,8-萘酰亚胺为环系，通过醚连接具有生物活性的3-甲基呋喃-2- 1单元的新型荧光己光内酯衍生物，并对其光谱性质进行了研究。利用电子吸收光谱和荧光光谱研究了这些哌啶-萘酰亚胺在不同极性溶剂中的溶剂致变色行为。考虑到溶剂极性的变化，这些化合物表现出强烈的正溶剂致变色，并通过荧光寿命测量分析了响应机理。根据Catalan和[f(n), f(ε), β， α]溶剂尺度，双极性和极化率是描述溶质-溶剂相互作用的相关参数。为了确定有机环境中的水分含量，讨论了发射化学感应活性。这些化合物的排放强度在二氧六环中迅速下降，使水位升高10%。量子产率的测定表明，这些衍生物在非极性溶剂中获得了最高的量子效率，而在极性溶剂中则显示出最低的量子产率。低水位时，荧光衰减可以用单指数模型来描述，高含水量时，荧光衰减可以用双指数模型来描述。
Novel fluorescent strigolactone derivatives that contain the piperidine-substituted 1,8-naphthalimide ring system connected through an ether link to a bioactive 3-methyl-furan-2-one unit were synthesized and their spectroscopic properties investigated. The solvatochromic behavior of these piperidine-naphthalimides was monitored in solvents of different polarity using the electronic absorption and fluorescence spectra. These compounds exhibited a strong positive solvatochromism taking into account the change of solvent polarity, and the response mechanism was analyzed by fluorescence lifetime measurements. According to Catalan and [f(n), f(ε), β, α] solvent scales, the dipolarity and polarizability are relevant to describe the solute–solvent interactions. The emission chemosensing activity was discussed in order to determine the water content in organic environments. The emission intensity of these compounds decreased rapidly in dioxane, increasing water level up to 10%. Measuring of quantum yield indicated that the highest values of quantum efficiency were obtained in nonpolar solvents, while in polar solvents these derivatives revealed the lowest quantum yield. The fluorescence decay can be described by a monoexponential model for low water levels, and for higher water contents a biexponential model was valid.
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