Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media
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 isolat...
| Main Authors: | , , , , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
2011
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| _version_ | 1797074900278575104 |
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| author | Evans, N Allinson, E Lankshear, MD Ng, K Cowley, A Serpell, C Santos, S Costa, P Felix, V Beer, P |
| author_facet | Evans, N Allinson, E Lankshear, MD Ng, K Cowley, A Serpell, C Santos, S Costa, P Felix, V Beer, P |
| author_sort | Evans, N |
| collection | OXFORD |
| description | 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. 1H 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. This journal is © The Royal Society of Chemistry 2011. |
| first_indexed | 2024-03-06T23:42:56Z |
| format | Journal article |
| id | oxford-uuid:6fecf6e7-d8e9-4b3b-a6d5-553a2f317271 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T23:42:56Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | oxford-uuid:6fecf6e7-d8e9-4b3b-a6d5-553a2f3172712022-03-26T19:33:51ZAnion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent mediaJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:6fecf6e7-d8e9-4b3b-a6d5-553a2f317271EnglishSymplectic Elements at Oxford2011Evans, NAllinson, ELankshear, MDNg, KCowley, ASerpell, CSantos, SCosta, PFelix, VBeer, PAn 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. 1H 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. This journal is © The Royal Society of Chemistry 2011. |
| spellingShingle | Evans, N Allinson, E Lankshear, MD Ng, K Cowley, A Serpell, C Santos, S Costa, P Felix, V Beer, P Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media |
| title | Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media |
| title_full | Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media |
| title_fullStr | Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media |
| title_full_unstemmed | Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media |
| title_short | Anion templated assembly of [2]catenanes capable of chloride anion recognition in aqueous solvent media |
| title_sort | anion templated assembly of 2 catenanes capable of chloride anion recognition in aqueous solvent media |
| work_keys_str_mv | AT evansn aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT allinsone aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT lankshearmd aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT ngk aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT cowleya aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT serpellc aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT santoss aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT costap aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT felixv aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia AT beerp aniontemplatedassemblyof2catenanescapableofchlorideanionrecognitioninaqueoussolventmedia |