Unlocking intrinsically chiral bipyrenyl-based aggregation-induced emission luminogens: circularly polarized luminescence and dynamic chirality amplification

TL;DR

This paper introduces new chiral compounds that show strong light emission and amplified chirality when aggregated, offering insights into designing better CPL materials.

Contribution

The paper introduces novel intrinsically chiral bipyrenyl enantiomers with dynamic chirality amplification and AIE properties.

Findings

R-5 and S-5 enantiomers show high solid-state fluorescence efficiency up to 0.66.

Amplified |gCD| values increase from 4.73 × 10−5 to 7.34 × 10−3 upon aggregation.

Amplified chiroptical properties result from helical self-assembly and prolonged excited-state reorganization.

Abstract

Understanding chiral dynamic mechanisms (from chirality generation and transfer, and amplification) is crucial for circularly polarized luminescent (CPL) materials. Herein, intrinsically chiral bipyrenyl-based enantiomers, R-5 and S-5, were first synthesized as model compounds to gain a deeper insight into their chiroptical properties and chirality amplification mechanisms. These enantiomers not only exhibit typical aggregation-induced emission (AIE) with a high solid-state fluorescence efficiency up to 0.66, but also display significant chirality amplification upon aggregation, with amplified |gCD| from 4.73 × 10−5 (10−7 M) to 7.34 × 10−3 (10−3 M), and |glum| values up to 4.68 × 10−4 in the solid state. Morphological and CP-fs-TA studies reveal that the amplified chiroptical properties stem from helical self-assembly and prolonged excited-state chiral conformational reorganization in aggregates. This work establishes a design strategy for high-performance CPL materials by integrating intrinsic chirality, AIE properties, and dynamic chirality amplification mechanisms.

This article presents two novel intrinsically chiral bipyrenyl-based enantiomers, R-5 and S-5, which were first synthesized as model compounds to gain a deeper insight into their chiroptical properties and chirality amplification mechanisms.

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