Unconventional Chiral Amplification in Luminescent Supramolecular Polymers Based on Trisbiphenylamine-tricarboxamides

Abstract

We describe the synthesis of two propeller-shaped, emissive trisbiphenylamines 1 and (S)-2. Whilst achiral 1 forms supramolecular polymers following a cooperative mechanism, the self-assembly of chiral (S)-2 can be described by an isodesmic mechanism. Despite the isodesmic character of the supramolecular polymerization of (S)-2, an efficient transfer of chirality from the embedded point chirality of the peripheral side chains to the aggregates is demonstrated. The co-assembly of 1 and (S)-2 in a sergeants-and-soldiers experiment shows a very different dichroic response to that registered for pristine (S)-2, with a copolymerization curve displaying two transitions. Both these transitions coincide with those observed for the pristine achiral and chiral components, thus suggesting a self-sorting effect.

Key words

Cooperativity - isodesmic - helical structures - supramolecular polymerization - triarylamines

Supporting Information

Supporting information for this article is available online at https://doi.org.

• References

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