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Synthesis of an anthracene-based diguanidine and its recognition of carboxylic acids and phosphonic acids
Tetrahedron ( IF 2.1 ) Pub Date : 2020-02-25 , DOI: 10.1016/j.tet.2020.131065
Takahiro Kusukawa , Ryosuke Mura , Yasuhiro Ohtagaki , Masashi Ooe

An anthracene-based diguanidine (1) for the recognition of carboxylic acids and phosphonic acids has been designed and synthesized. The diguanidine 1 forms 1:1 complexes with the dicarboxylic acids and diphosphonic acids in a DMSO solution, and the formation of the 1:1 complexes was determined by DOSY NMR spectroscopy. For the recognition of methylphosphonic acid (monophosphonic acid), the formation of the 1:2 complex was also determined. The diguanidine 1 shows a characteristic yellow fluorescence in a DMSO solution that may be caused by the weak aggregation of 1 which was estimated by dilution fluorescence studies. However, after the addition of the dicarboxylic acids (30 equiv.), the yellow fluorescence of 1 disappeared (turned off the fluorescence). On the other hand, after the addition of diphosphonic acids (1 equiv.) and methylphosphonic acid (2 equiv.), the yellow emission turned to purple. These fluorescence characteristics of the diguanidine 1 are also applicable for the detection of carboxylic acids and phosphonic acids.



中文翻译:

蒽基双胍的合成及其对羧酸和膦酸的识别

已经设计并合成了用于识别羧酸和膦酸的基于蒽的双胍(1)。二胍1在DMSO溶液中与二羧酸和二膦酸形成1:1配合物,并通过DOSY NMR光谱法确定1:1配合物的形成。为了识别甲基膦酸(单膦酸),还确定了1:2络合物的形成。双胍1在DMSO溶液中显示出特征性的黄色荧光,这可能是由于1的弱聚集所引起的,而弱聚集是通过稀释荧光研究估计的。但是,添加二羧酸(30当量)后,黄色荧光为1消失(关闭荧光)。另一方面,在添加二膦酸(1当量)和甲基膦酸(2当量)之后,黄色发射变成紫色。双胍1的这些荧光特性也可用于检测羧酸和膦酸。

更新日期:2020-02-25
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