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Recognition of carboxylic acids and phosphonic acids using 1,8-diphenylnaphthalene-based diguanidine
Tetrahedron ( IF 2.1 ) Pub Date : 2020-11-17 , DOI: 10.1016/j.tet.2020.131770
Takahiro Kusukawa , Ryosuke Mura , Masashi Ooe , Ryuki Sumida , Ayaka Nakagawa

A diphenylnaphthalene-based diguanidine (1) has been designed and synthesized for the recognition of dicarboxylic acids and diphosphonic acids. The diguanidine 1 forms 1:1 complexes with the dicarboxylic acids and the diphosphonic acid derivatives in a DMSO solution, and the formation of the complexes was determined by DOSY NMR spectroscopy. The weak yellowish fluorescence of the diguanidine 1 in a DMSO solution turned to a strong bluish fluorescence after the addition of 1,3-benzenediacetic acids 3. However, after the addition of other types of aliphatic dicarboxylic acids, such as α,ω-dicarboxylic acids, only a weak yellowish fluorescence was observed and selective recognition of the 1,3-benzenediacetic acids 3 was developed. On the other hand, for the recognition of diphosphonic acid derivatives (57), a light blue, blue or pinkish fluorescence was observed. Interestingly, the binding mode on the guanidyl group (two existing types of binding modes toward three nitrogen atoms) with oxoacids were successfully determined by the 2D NOESY analysis. The fluorescence quantum yields (Φfl) were moderately increased by the introduction of the guanidyl group and binding with dicarboxylic acids 3 than that of the 1,8-diphenylnaphthalene itself. These fluorescence characteristics of the diguanidine 1 are applicable for the detection of dicarboxylic acids and diphosphonic acids.



中文翻译:

使用基于1,8-二苯基萘的双胍识别羧酸和膦酸

已经设计并合成了基于二苯基萘的二胍(1),用于识别二羧酸和二膦酸。二胍1在DMSO溶液中与二羧酸和二膦酸衍生物形成1∶1的配合物,并通过DOSY NMR光谱法确定配合物的形成。的二胍的弱淡黄色荧光1在DMSO溶液变成强带蓝色的荧光添加后1,3 -苯二羧酸3。但是,添加其他类型的脂族二羧酸后,例如αω-二羧酸,仅观察到微弱的淡黄色荧光,并且选择性识别了1,3-苯二乙酸3。在另一方面,对于识别二膦酸衍生物(的5 - 7),淡蓝色,观察到蓝色或粉红色荧光。有趣的是,通过二维NOESY分析成功地确定了胍基与含氧酸的结合模式(两种现有的向三个氮原子的结合模式)。荧光量子产率(Φ FL)的适度增加通过引入胍基的并与二羧酸结合3比1,8-二苯基萘本身的 二胍1的这些荧光特性可用于检测二羧酸和二膦酸。

更新日期:2020-12-16
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