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Bispidine as a Versatile Scaffold: From Topological Hosts to Transmembrane Transporters.
Hanuman Singh1, Nadira Khatoon2, Surya Kant Bhardwaj1
1Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110016, India.
Chembiochem : a European Journal of Chemical Biology
|September 14, 2023
Summary
Bispidine serves as a versatile platform for creating designer molecules with unique S-shape topologies and self-assembling tubular structures. These structures show potential for ion transport applications, highlighting novel nanotube fabrication methods.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Materials Science
Background:
- Designing molecules with specific topologies is synthetically complex.
- Bispidine offers a novel scaffold for creating diverse molecular architectures.
Purpose of the Study:
- To introduce bispidine as a platform for designing molecules with varied topologies and functions.
- To investigate the ionophoric properties and self-assembly of bispidine-based macrocycles.
- To explore the use of dihydrogen bonding in nanotube fabrication.
Main Methods:
- Synthesis of bispidine-based acyclic molecules and macrocycles.
- Single-crystal X-ray diffraction for structural analysis.
- Patch clamp electrophysiology for ion transport studies.
- Ultramicroscopy for visualizing self-assembled structures.
Main Results:
- An S-shaped acyclic bispidine molecule was synthesized, existing as two conformational enantiomers in the solid state.
- Bispidine-based macrocycles demonstrated non-specific transport of both anions and cations.
- Chloride conductance was significantly higher (at least tenfold) than cation conductance.
- Self-assembly of macrocycles formed tubular structures, confirmed by ultramicroscopy and X-ray crystallography.
Conclusions:
- Bispidine is an effective platform for creating designer molecules with controlled topologies.
- Bispidine-based macrocycles exhibit ionophoric properties and self-assemble into nanotubes.
- Unconventional dihydrogen interactions play a key role in the fabrication of these supramolecular nanotubes.
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