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Controlling the Helical Pitch of Foldamers through Terminal Functionality: A Solid State Study.

Alexander R Davis1, Sena Ozturk1, Colin C Seaton2

  • 1School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 9, 2024
PubMed
Summary

Controlling foldamer helical structures is key for function. This study shows that changing foldamer end groups can easily double the helical pitch, offering new ways to design these molecular scaffolds.

Keywords:
Conformation analysisCrystallographyFoldamersSolid-state structuresSupramolecular chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Foldamers are synthetic polymers that mimic biological macromolecules.
  • The secondary structure of foldamers, such as helical pitch, is critical for their function.
  • Controlling foldamer secondary structure is essential for developing novel molecular scaffolds.

Purpose of the Study:

  • To investigate the effect of terminal functionalities on the helical pitch of ortho-azobenzene/2,6-pyridyldicarboxamide foldamers.
  • To establish a method for readily controlling foldamer size and shape.
  • To provide insights for the rational design of functional foldamers.

Main Methods:

  • Synthesis of a library of ortho-azobenzene/2,6-pyridyldicarboxamide foldamers with varying terminal functionalities.
  • Characterization of foldamer structures using crystallographic analysis.
  • Systematic variation of end groups including carboxylbenzyl (Cbz), diphenylcarbamyl (N(Ph)2), ferrocene (Fc), and tert-butyloxycarbonyl (Boc).

Main Results:

  • The helical pitch of foldamers can be significantly altered by changing terminal functionalities.
  • Helical pitch was observed to more than double, ranging from 3.4 Å to 7.3 Å.
  • Crystallographic analysis revealed general trends in how different end groups influence folding behavior.

Conclusions:

  • Terminal functionality is a powerful tool for controlling foldamer helical pitch and overall shape.
  • This work provides a facile method for tuning foldamer secondary structure.
  • The findings can guide the future development of precisely shaped functional foldamers for various applications.