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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
Author(s) -
Byrne Joseph P.,
Blasco Salvador,
Aletti Anna B.,
Hessman Gary,
Gunnlaugsson Thorfinnur
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201603213
Subject(s) - catenane , chemistry , hydrogen bond , pyridine , olefin metathesis , olefin fiber , ring (chemistry) , crystallography , ring closing metathesis , amide , triazole , stereochemistry , metathesis , combinatorial chemistry , molecule , organic chemistry , polymerization , catalysis , polymer
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 CH 2 Cl 2 . X‐ray diffraction crystallography enabled the structural characterization of both the [2]catenane 3 a and the non‐interlocked macrocycle 4 a . These [2]catenanes showed selective triazolyl hydrogen‐bonding interactions with the tetrahedral phosphate anion when screened against a range of ions; 3 a , b are the first examples of selective [2]catenane hosts for phosphate.