Acid-Base Switchable [2]- and [3]Rotaxane Molecular Shuttles with Benzimidazolium and Bis(pyridinium) Recognition Sites
| Autor: | V. Nicholas Vukotic, Kelong Zhu, Stephen J. Loeb |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
Molecular switch
Rotaxane 010405 organic chemistry Stereochemistry Organic Chemistry Supramolecular chemistry General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Molecular machine 0104 chemical sciences chemistry.chemical_compound Molecular shuttle chemistry Proton NMR Molecule Pyridinium |
| Zdroj: | Chemistry - An Asian Journal. 11:3258-3266 |
| ISSN: | 1861-4728 |
| DOI: | 10.1002/asia.201601179 |
| Popis: | For the purpose of developing higher level mechanically interlocked molecules (MIMs), such as molecular switches and machines, a new rotaxane system was designed in which both the 1,2 bis(pyridinium)ethane and benzimidazolium recognition templating motifs were combined. These two very different recognition sites were successfully incorporatedinto [2]rotaxane and [3]rotaxane molecular shuttles which were fully characterized by 1H NMR, 2D EXSY, single crystal X-ray diffraction and VT NMR analysis. By utilizing benzimidazolium as both a recognition site and stoppering group it was possible to create, not only, an acid/base switchable [2]rotaxane molecular shuttle (energy barrier 20.9 kcal*mol‒1) but also a [3]rotaxane molecular shuttle that undergoes a unique dynamic involving the simultaneous motion of two macrocyclic wheels on a single dumbbell. This study provides new insights into the design of switchable molecular shuttles. Due to the unique properties of benzimidazoles, such as fluorescence and metal coordination, this new type of molecular shuttle may find further applications in developing functional molecular machines and materials. |
| Databáze: | OpenAIRE |
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