Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media
AU - Evans, Nicholas H.
AU - Allinson, Emma S. H.
AU - Lankshear, Michael D.
AU - Ng, Ka-Yuen
AU - Cowley, Andrew R.
AU - Serpell, Christopher J.
AU - Santos, Sergio M.
AU - Costa, Paulo J.
AU - Felix, Vitor
AU - Beer, Paul D.
PY - 2011/10/21
Y1 - 2011/10/21
N2 - An anion templated double cyclization strategy to synthesize [2]catenanes in which two identical acyclic pyridinium receptor motifs interweave around a chloride anion template is described. Ring closing metathesis (RCM) of the preorganized orthogonal precursor chloride complex facilitates the isolation of [2] catenanes in very high yields. X-ray crystal structures provide an insight of the supramolecular forces responsible for chloride anion templated efficacy and recognition. Removal of the chloride anion template generates topologically unique interlocked binding cavities for anions. H-1 NMR anion binding investigations demonstrate the catenanes to be highly selective hosts for chloride in preference to more basic monocharged oxoanions. In aqueous solvent media containing 30% water, such catenanes exclusively bind chloride, under which conditions no binding of acetate or dihydrogen phosphate is observed. Molecular dynamic simulations in the solution phase are used to account for the catenanes' anion recognition properties.
AB - An anion templated double cyclization strategy to synthesize [2]catenanes in which two identical acyclic pyridinium receptor motifs interweave around a chloride anion template is described. Ring closing metathesis (RCM) of the preorganized orthogonal precursor chloride complex facilitates the isolation of [2] catenanes in very high yields. X-ray crystal structures provide an insight of the supramolecular forces responsible for chloride anion templated efficacy and recognition. Removal of the chloride anion template generates topologically unique interlocked binding cavities for anions. H-1 NMR anion binding investigations demonstrate the catenanes to be highly selective hosts for chloride in preference to more basic monocharged oxoanions. In aqueous solvent media containing 30% water, such catenanes exclusively bind chloride, under which conditions no binding of acetate or dihydrogen phosphate is observed. Molecular dynamic simulations in the solution phase are used to account for the catenanes' anion recognition properties.
KW - OLEFIN METATHESIS CATALYSTS
KW - STABILITY-CONSTANTS
KW - ROTAXANE SYNTHESIS
KW - CATENANES
KW - INTERLOCKING
KW - PSEUDOROTAXANES
KW - MACROCYCLE
KW - MACHINES
KW - RING
U2 - 10.1039/c1ra00394a
DO - 10.1039/c1ra00394a
M3 - Journal article
VL - 1
SP - 995
EP - 1003
JO - RSC Advances
JF - RSC Advances
SN - 2046-2069
IS - 6
ER -