Helicity induction and memory of a lipophilic Brønsted acid-type poly(phenylacetylene) in non-polar solvents

Chem Commun (Camb). 2023 Jun 29;59(53):8226-8229. doi: 10.1039/d3cc01521a.

Abstract

A novel lipophilic Brønsted acid-type PPA (poly-1-H) bearing a sulfonylphosphoramidic acid moiety, covered with a dynamically axially chiral biphenyl pendant, was synthesized and found to form a preferred-handed helical conformation in non-polar solvents upon complexation with non-racemic amines. This induced helicity was maintained after replacement with achiral amines ("dynamic helicity memory"). In addition, poly-1-H exhibited "static helicity memory" in which the induced helical conformation was maintained in non-polar solvents, even after acidification with a stronger acid without replacement with achiral amines.

MeSH terms

  • Acetylene*
  • Amines*
  • Solvents

Substances

  • poly(phenylacetylene)
  • Solvents
  • Acetylene
  • phenylacetylene
  • Amines