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Strain-induced helical chirality in polyaromatic systems.

Michel Rickhaus1, Marcel Mayor2, Michal Juríček1

  • 1Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland. marcel.mayor@unibas.ch.

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|January 15, 2016
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Summary
This summary is machine-generated.

Molecular helicity can be induced in non-chiral molecules by introducing steric strain, favoring a helical twist over a planar form. This review analyzes design principles and categorizes examples based on helical ribbon structures.

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Area of Science:

  • Organic Chemistry
  • Stereochemistry
  • Molecular Design

Background:

  • Helicity in molecules is typically associated with stereogenic axes, not centers.
  • Achieving molecular helicity in non-inherently chiral molecules requires specific design strategies.

Purpose of the Study:

  • To analyze the design principles for inducing helicity in molecules.
  • To categorize molecules based on their structural relationship to helical ribbons.
  • To explore the structure-property relationships of induced helicity.

Main Methods:

  • Analysis of design principles for inducing molecular strain.
  • Categorization of examples into five classes (I-V) based on helical ribbon structures.
  • Review of solid-state structures and racemization energy barriers.

Main Results:

  • Identified key design principles involving the balance between steric strain release and torsional strain.
  • Classified examples according to their structural relation to three types of helical ribbons and two types of cyclic helical ribbons.
  • Highlighted cases where induced helicity leads to novel phenomena.

Conclusions:

  • Molecular strain can effectively induce helicity in planar conformations.
  • Categorization provides a framework for understanding induced helicity in diverse molecular architectures.
  • The interplay between strain and torsional forces is crucial for favoring helical conformations.