Formation of Self-Templated 2,6-Bis(1,2,3-triazol-4-yl)pyridine [2]Catenanes by Triazolyl Hydrogen Bonding: Selective Anion Hosts for Phosphate

被引:46
作者
Byrne, Joseph P. [1 ,2 ,3 ]
Blasco, Salvador [1 ,2 ]
Aletti, Anna B. [1 ,2 ]
Hessman, Gary [1 ,2 ]
Gunnlaugsson, Thorfinnur [1 ,2 ]
机构
[1] Univ Dublin, Sch Chem, Dublin 2, Ireland
[2] Univ Dublin, Trinity Coll Dublin, Trinity Biomed Sci Inst, Dublin 2, Ireland
[3] Univ Bern, Dept Chem & Biochem, Freiestr 3, CH-3012 Bern, Switzerland
基金
爱尔兰科学基金会;
关键词
anion hosts; catenanes; ring-closing metathesis; self-templating; triazoles; RING-CLOSING METATHESIS; METALLO-SUPRAMOLECULAR GELS; AQUEOUS SOLVENT MEDIA; ASSEMBLY FORMATION; BTP LIGANDS; MOLECULAR KNOTS; RECOGNITION; CATENANE; COMPLEXES; ROTAXANES;
D O I
10.1002/anie.201603213
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the remarkable ability of 2,6-bis(1,2,3-triazol-4-yl)pyridine (btp) compounds 2 with appended olefin amide arms to self-template the formation of interlocked [2]catenane structures 3 in up to 50% yield when subjected to olefin ring-closing metathesis in CH2Cl2. X-ray diffraction crystallography enabled the structural characterization of both the [2] catenane 3a and the non-interlocked macrocycle 4a. These [2]catenanes showed selective triazolyl hydrogen-bonding interactions with the tetrahedral phosphate anion when screened against a range of ions; 3a,b are the first examples of selective [2]catenane hosts for phosphate.
引用
收藏
页码:8938 / 8943
页数:6
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