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Dynamic Axial‐to‐Helical Communication Mechanism in Poly[(allenylethynylenephenylene)acetylene]s under External Stimuli

María Lago‐Silva, Marı́a Magdalena Cid, Emilio Quiñoá, Félix Freire

2023Angewandte Chemie International Edition15 citationsDOIOpen Access PDF

Abstract

Helix inversion in chiral dynamic helical polymers is usually achieved by conformational changes at the pendant groups induced through external stimuli. Herein, a different mechanism of helix inversion in poly(phenylacetylene)s (PPAs) is presented, based on the activation/deactivation of supramolecular interactions. We prepared poly[(allenylethynylenephenylene)acetylene]s (PAEPAs) in which the pendant groups are conformationally locked chiral allenes. Therefore, their substituents are placed in specific spatial orientations. As a result, the screw sense of a PAEPA is fixed by the allenyl substituent with the optimal size/distance relationship to the backbone. This helical sense command can be surpassed by supramolecular interactions between another substituent on the allene and appropriate external stimuli, such as amines. So, a helix inversion occurs through a novel axial-to-helical communication mechanism, opening a new scenario for taming the helices of chiral dynamic helical polymers.

Topics & Concepts

PhenylacetyleneSubstituentAcetyleneHelix (gastropod)Supramolecular chemistryChemistryAllenePolymerStereochemistryCrystallographyMaterials scienceCrystal structureCatalysisOrganic chemistrySnailBiologyEcologySynthesis and Properties of Aromatic CompoundsSupramolecular Self-Assembly in MaterialsSupramolecular Chemistry and Complexes