Phenazine-1,6-dicarboxamides: Redox-Responsive Molecular Switches
Jingwei Yin1, Ali N Khalilov1, Pandi Muthupandi1
1Department of Chemistry , Washington University , Campus Box 1134, One Brookings Drive , Saint Louis , Missouri 63130 , United States.
Journal of the American Chemical Society
|December 25, 2019
Summary
New molecular switches, phenazine-1,6-dicarboxamides, change from hydrogen-bond acceptors to donors upon reduction. This redox-triggered change enables reversible conformational changes for advanced materials.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Molecular switches are crucial for developing responsive materials.
- Controlling molecular conformation through external stimuli is a key challenge in materials science.
Purpose of the Study:
- To introduce phenazine-1,6-dicarboxamides as novel redox-responsive molecular switches.
- To explore the potential of these compounds in creating dynamic foldamer structures.
Main Methods:
- Synthesis of phenazine-1,6-dicarboxamide derivatives.
- Investigation of their redox properties and conformational changes using spectroscopic and computational methods.
Main Results:
- Phenazine-1,6-dicarboxamides function as effective redox-responsive molecular switches.
- Reduction of the phenazine core induces a transformation from hydrogen-bond acceptors to donors.
- This results in a significant conformational change of the amide substituents.
Conclusions:
- Phenazine-1,6-dicarboxamides offer a new platform for redox-controlled molecular devices.
- The observed conformational changes can be the basis for butterfly coil foldamers with reversible extension and contraction.
- These findings open avenues for designing dynamic materials responsive to oxidation state changes.
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