Redox-Dependent Conformational Switching of Diphenylacetylenes
Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy o...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2014-07-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/19/8/11316 |
| _version_ | 1811278375216480256 |
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| author | Ian M. Jones Peter C. Knipe Thoe Michaelos Sam Thompson Andrew D. Hamilton |
| author_facet | Ian M. Jones Peter C. Knipe Thoe Michaelos Sam Thompson Andrew D. Hamilton |
| author_sort | Ian M. Jones |
| collection | DOAJ |
| description | Herein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch. |
| first_indexed | 2024-04-13T00:34:28Z |
| format | Article |
| id | doaj.art-848dcffc5a534ed78552bb2299b7f17b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T00:34:28Z |
| publishDate | 2014-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-848dcffc5a534ed78552bb2299b7f17b2022-12-22T03:10:22ZengMDPI AGMolecules1420-30492014-07-01198113161133210.3390/molecules190811316molecules190811316Redox-Dependent Conformational Switching of DiphenylacetylenesIan M. Jones0Peter C. Knipe1Thoe Michaelos2Sam Thompson3Andrew D. Hamilton4Chemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UKChemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UKDepartment of Chemistry, Yale University, P. O. Box 208107, New Haven, CT 06520-8107, USAChemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UKChemistry Research Laboratory, Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UKHerein we describe the design and synthesis of a redox-dependent single-molecule switch. Appending a ferrocene unit to a diphenylacetylene scaffold gives a redox-sensitive handle, which undergoes reversible one-electron oxidation, as demonstrated by cyclic voltammetry analysis. 1H-NMR spectroscopy of the partially oxidized switch and control compounds suggests that oxidation to the ferrocenium cation induces a change in hydrogen bonding interactions that results in a conformational switch.http://www.mdpi.com/1420-3049/19/8/11316molecular switchferrocenehydrogen bondingamide bondredoxtranslational isomerism |
| spellingShingle | Ian M. Jones Peter C. Knipe Thoe Michaelos Sam Thompson Andrew D. Hamilton Redox-Dependent Conformational Switching of Diphenylacetylenes Molecules molecular switch ferrocene hydrogen bonding amide bond redox translational isomerism |
| title | Redox-Dependent Conformational Switching of Diphenylacetylenes |
| title_full | Redox-Dependent Conformational Switching of Diphenylacetylenes |
| title_fullStr | Redox-Dependent Conformational Switching of Diphenylacetylenes |
| title_full_unstemmed | Redox-Dependent Conformational Switching of Diphenylacetylenes |
| title_short | Redox-Dependent Conformational Switching of Diphenylacetylenes |
| title_sort | redox dependent conformational switching of diphenylacetylenes |
| topic | molecular switch ferrocene hydrogen bonding amide bond redox translational isomerism |
| url | http://www.mdpi.com/1420-3049/19/8/11316 |
| work_keys_str_mv | AT ianmjones redoxdependentconformationalswitchingofdiphenylacetylenes AT petercknipe redoxdependentconformationalswitchingofdiphenylacetylenes AT thoemichaelos redoxdependentconformationalswitchingofdiphenylacetylenes AT samthompson redoxdependentconformationalswitchingofdiphenylacetylenes AT andrewdhamilton redoxdependentconformationalswitchingofdiphenylacetylenes |