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Sensing a binding event through charge transport variations using an aromatic oligoamide capsule.
Pedro Mateus1, Antoine Jacquet1, Alejandro Méndez-Ardoy2
1Univ. Bordeaux, CNRS, Bordeaux INP, UMR 5248 CBMN, IECB 2 rue Escarpit 33600 Pessac France.
Chemical Science
|June 24, 2021
Summary
This study reports a foldamer capsule that selectively binds dicarboxylic acids. The capsule
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Oligoamide foldamer capsules offer unique binding properties.
- Designing selective molecular recognition systems is crucial for chemical sensing and drug delivery.
- Understanding host-guest interactions at the molecular level is key to developing new functional materials.
Purpose of the Study:
- To investigate the selective binding of dicarboxylic acids by a designed oligoamide foldamer capsule.
- To explore the mechanism of guest binding, including protonation/deprotonation events and structural changes.
- To evaluate the performance of foldamer capsules in self-assembled monolayers for electronic applications.
Main Methods:
- Synthesis and characterization of 13-mer and 14-mer oligoamide foldamer capsules.
- Solution-state Nuclear Magnetic Resonance (NMR) spectroscopy.
- Single-crystal X-ray diffraction.
- Surface characterization using ellipsometry and polarization-modulation infrared absorption-reflection spectroscopy (PM-IRRAS).
- Conducting Atomic Force Microscopy (c-AFM).
Main Results:
- The foldamer capsule selectively binds dicarboxylic acids, with fluorinated succinic acids inducing symmetry breaking due to mono-deprotonation.
- NMR and X-ray diffraction confirmed the binding mechanism and structural changes upon guest encapsulation.
- Foldamer capsules form vertically oriented monolayers on gold surfaces.
- Complexation of 2,2-difluorosuccinic acid by the monolayer capsule resulted in a significant 80-fold decrease in charge transport.
- Conductivity modulation was attributed to protonation of the foldamer backbone.
Conclusions:
- Oligoamide foldamer capsules can be designed for selective recognition of dicarboxylic acids.
- The binding process involves intricate interplay of protonation, H-bonding, and structural constraints.
- Foldamer-based monolayers exhibit tunable electronic properties upon guest complexation, paving the way for molecular electronics.
- This work demonstrates the potential of foldamer capsules in sensing and electronic device applications.
