How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?
Interlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of in...
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| Format: | Article |
| Language: | English |
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MDPI AG
2017-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/11/2017 |
| _version_ | 1811209091704422400 |
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| author | Benjamin Riss-Yaw Justine Morin Caroline Clavel Frédéric Coutrot |
| author_facet | Benjamin Riss-Yaw Justine Morin Caroline Clavel Frédéric Coutrot |
| author_sort | Benjamin Riss-Yaw |
| collection | DOAJ |
| description | Interlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of interactions for crown ethers, the very straightforwardly obtained amide motif has more rarely been envisaged as molecular station. In this article, we report the use of secondary and tertiary amide moieties as efficient secondary molecular station in pH-sensitive molecular shuttles. Depending on the N-substitution of the amide station, and on deprotonation or deprotonation-carbamoylation, the actuation of the molecular machinery differs accordingly to very distinct interactions between the axle and the DB24C8. |
| first_indexed | 2024-04-12T04:33:33Z |
| format | Article |
| id | doaj.art-88610b2789a04c459f8f6df81b03a968 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T04:33:33Z |
| publishDate | 2017-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-88610b2789a04c459f8f6df81b03a9682022-12-22T03:47:52ZengMDPI AGMolecules1420-30492017-11-012211201710.3390/molecules22112017molecules22112017How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles?Benjamin Riss-Yaw0Justine Morin1Caroline Clavel2Frédéric Coutrot3Supramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, Université Montpellier, ENSCM, Case Courrier 1706, Bâtiment Chimie (17), 3ème étage, Faculté des Sciences, Place Eugène Bataillon, 34095 Montpellier CEDEX 5, FranceSupramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, Université Montpellier, ENSCM, Case Courrier 1706, Bâtiment Chimie (17), 3ème étage, Faculté des Sciences, Place Eugène Bataillon, 34095 Montpellier CEDEX 5, FranceSupramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, Université Montpellier, ENSCM, Case Courrier 1706, Bâtiment Chimie (17), 3ème étage, Faculté des Sciences, Place Eugène Bataillon, 34095 Montpellier CEDEX 5, FranceSupramolecular Machines and ARchitectures Team, Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS, Université Montpellier, ENSCM, Case Courrier 1706, Bâtiment Chimie (17), 3ème étage, Faculté des Sciences, Place Eugène Bataillon, 34095 Montpellier CEDEX 5, FranceInterlocked molecular machines like [2]rotaxanes are intriguing aesthetic molecules. The control of the localization of the macrocycle, which surrounds a molecular axle, along the thread leads to translational isomers of very different properties. Although many moieties have been used as sites of interactions for crown ethers, the very straightforwardly obtained amide motif has more rarely been envisaged as molecular station. In this article, we report the use of secondary and tertiary amide moieties as efficient secondary molecular station in pH-sensitive molecular shuttles. Depending on the N-substitution of the amide station, and on deprotonation or deprotonation-carbamoylation, the actuation of the molecular machinery differs accordingly to very distinct interactions between the axle and the DB24C8.https://www.mdpi.com/1420-3049/22/11/2017molecular machinerotaxaneamideammoniumaminedibenzo-24-crown-8template |
| spellingShingle | Benjamin Riss-Yaw Justine Morin Caroline Clavel Frédéric Coutrot How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? Molecules molecular machine rotaxane amide ammonium amine dibenzo-24-crown-8 template |
| title | How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? |
| title_full | How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? |
| title_fullStr | How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? |
| title_full_unstemmed | How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? |
| title_short | How Secondary and Tertiary Amide Moieties are Molecular Stations for Dibenzo-24-crown-8 in [2]Rotaxane Molecular Shuttles? |
| title_sort | how secondary and tertiary amide moieties are molecular stations for dibenzo 24 crown 8 in 2 rotaxane molecular shuttles |
| topic | molecular machine rotaxane amide ammonium amine dibenzo-24-crown-8 template |
| url | https://www.mdpi.com/1420-3049/22/11/2017 |
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