Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions
The Lewis acidic redox-active and photoactive ruthenium(II) bipyridyl moiety in combination with amide (CO-NH) groups has been incorporated into acyclic, macrocyclic, and lower rim calix[4]arene structural frameworks to produce a new class of anion receptor with the dual capability of sensing anioni...
| Main Authors: | , , , , , , , , , , , |
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| Format: | Journal article |
| Published: |
1996
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| _version_ | 1797068673254424576 |
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| author | Szemes, F Hesek, D Chen, Z Dent, S Drew, M Goulden, A Graydon, A Grieve, A Mortimer, R Wear, T Weightman, J Beer, P |
| author_facet | Szemes, F Hesek, D Chen, Z Dent, S Drew, M Goulden, A Graydon, A Grieve, A Mortimer, R Wear, T Weightman, J Beer, P |
| author_sort | Szemes, F |
| collection | OXFORD |
| description | The Lewis acidic redox-active and photoactive ruthenium(II) bipyridyl moiety in combination with amide (CO-NH) groups has been incorporated into acyclic, macrocyclic, and lower rim calix[4]arene structural frameworks to produce a new class of anion receptor with the dual capability of sensing anionic guest species via electrochemical and optical methodologies. Single-crystal X-ray structures of (1)Cl and (11)H2PO4 reveal the importance of hydrogen bonding to the overall anion complexation process. In the former complex, six hydrogen bonds (two amide and four C-H groups) stabilize the Cl- anion and three hydrogen bonds (two amide and one calix[4]arene hydroxyl) effect H2PO4 - complexation with 11. Proton NMR titration investigations in deuterated DMSO solutions reveal these receptors form strong and, in the case of the macrocyclic 5 and calix[4]arene-containing receptor 11, highly selective complexes with H2PO4 -. Cyclic and square-wave voltammetric studies have demonstrated these receptors to electrochemically recognize Cl-, Br-, H2PO4 -, and HSO4 - anions. The calix[4]arene anion receptor 11 selectively electrochemically senses H2PO4 - in the presence of 10-fold excess amounts of HSO4 - and Cl-. Fluorescence emission spectral recognition of H2PO4 - in DMSO solutions is displayed by 3, 5, and 11. |
| first_indexed | 2024-03-06T22:13:33Z |
| format | Journal article |
| id | oxford-uuid:52a333da-7b6d-46c1-8648-03265f9c684b |
| institution | University of Oxford |
| last_indexed | 2024-03-06T22:13:33Z |
| publishDate | 1996 |
| record_format | dspace |
| spelling | oxford-uuid:52a333da-7b6d-46c1-8648-03265f9c684b2022-03-26T16:26:42ZSynthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anionsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:52a333da-7b6d-46c1-8648-03265f9c684bSymplectic Elements at Oxford1996Szemes, FHesek, DChen, ZDent, SDrew, MGoulden, AGraydon, AGrieve, AMortimer, RWear, TWeightman, JBeer, PThe Lewis acidic redox-active and photoactive ruthenium(II) bipyridyl moiety in combination with amide (CO-NH) groups has been incorporated into acyclic, macrocyclic, and lower rim calix[4]arene structural frameworks to produce a new class of anion receptor with the dual capability of sensing anionic guest species via electrochemical and optical methodologies. Single-crystal X-ray structures of (1)Cl and (11)H2PO4 reveal the importance of hydrogen bonding to the overall anion complexation process. In the former complex, six hydrogen bonds (two amide and four C-H groups) stabilize the Cl- anion and three hydrogen bonds (two amide and one calix[4]arene hydroxyl) effect H2PO4 - complexation with 11. Proton NMR titration investigations in deuterated DMSO solutions reveal these receptors form strong and, in the case of the macrocyclic 5 and calix[4]arene-containing receptor 11, highly selective complexes with H2PO4 -. Cyclic and square-wave voltammetric studies have demonstrated these receptors to electrochemically recognize Cl-, Br-, H2PO4 -, and HSO4 - anions. The calix[4]arene anion receptor 11 selectively electrochemically senses H2PO4 - in the presence of 10-fold excess amounts of HSO4 - and Cl-. Fluorescence emission spectral recognition of H2PO4 - in DMSO solutions is displayed by 3, 5, and 11. |
| spellingShingle | Szemes, F Hesek, D Chen, Z Dent, S Drew, M Goulden, A Graydon, A Grieve, A Mortimer, R Wear, T Weightman, J Beer, P Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions |
| title | Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions |
| title_full | Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions |
| title_fullStr | Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions |
| title_full_unstemmed | Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions |
| title_short | Synthesis and characterization of novel acyclic, macrocyclic, and calix[4]arene ruthenium(II) bipyridyl receptor molecules that recognize and sense anions |
| title_sort | synthesis and characterization of novel acyclic macrocyclic and calix 4 arene ruthenium ii bipyridyl receptor molecules that recognize and sense anions |
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