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Xiaowu Yang1, Lihua Yuan, Kazuhiro Yamato

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Area of Science:

  • Supramolecular Chemistry
  • Polymer Science
  • Organic Chemistry

Background:

  • Oligo(m-phenylene ethynylenes) (oligo(m-PE)) are known to fold into conformations driven by external factors like solvents.
  • Achieving stable, backbone-independent folded structures in oligomers remains a challenge.

Purpose of the Study:

  • To synthesize and characterize oligo(m-PE) with backbones rigidified by intramolecular hydrogen bonds.
  • To investigate the conformational stability and folding behavior of these novel oligomers.
  • To establish a new design principle for creating resilient, folded unnatural oligomers.

Main Methods:

  • Synthesis of oligo(m-PE) with two to seven residues.
  • Characterization using 1D and 2D (1)H NMR spectroscopy and UV spectroscopy.
  • Computational analysis including ab initio and molecular mechanics calculations.

Main Results:

  • Oligomers with intramolecular hydrogen bonds were successfully synthesized and demonstrated to fold into well-defined, curved conformations.
  • Persistence of intramolecular hydrogen bonds and helical structures (pentamer, hexamer, heptamer) confirmed.
  • Backbone-based conformational programming resulted in structures resilient to side group variations.

Conclusions:

  • Intramolecular hydrogen bonds provide a robust method for achieving stable, folded oligo(m-PE) structures.
  • This approach offers an alternative to solvent-driven folding for creating unnatural foldamers.
  • The design principle enables the development of stably folded molecules with potential applications.