High-Affinity Hybridization of Complementary Aromatic Oligoamide Strands in Water

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry
• Materials Science

Background:

• Aromatic oligoamides offer a versatile platform for constructing ordered molecular architectures.
• Designing self-assembling systems with predictable structures and functions is a key challenge in supramolecular chemistry.

Purpose of the Study:

• To design and synthesize water-soluble aromatic oligoamide sequences capable of forming stable antiparallel duplexes.
• To investigate the selective hybridization of chemically distinct strands within these duplexes.
• To explore the potential of these hetero-duplexes for constructing dynamic supramolecular assemblies.

Main Methods:

• Synthesis of water-soluble aromatic oligoamide sequences with distinct helical and dimerization segments.
• Characterization of self-assembly using X-ray crystallography to confirm antiparallel duplex formation.
• Assessment of hybridization extent and kinetics via NMR spectroscopy and mass spectrometry.
• Systematic modification of duplex inner rim substituents to control strand complementarity.

Main Results:

• A series of water-soluble aromatic oligoamides were successfully prepared, exclusively forming antiparallel duplexes.
• Modification of substituents enabled selective hybridization between two chemically different strands with high affinity in water.
• X-ray crystallography confirmed the antiparallel duplex configuration.
• NMR and mass spectrometry validated the extent of hybridization.
• Hybridization kinetics were found to depend on strand complementarity and length.

Conclusions:

• Aromatic hetero-duplexes can be selectively formed in water from chemically distinct strands.
• These systems demonstrate high affinity and selectivity, offering precise control over supramolecular assembly.
• The findings highlight the potential of aromatic hetero-duplexes as building blocks for non-symmetrical dynamic supramolecular structures.