High-Fidelity Supramolecular Chirality Transportation Enabled Through Chalcogen Bonding.

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Key Laboratory of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, P. R. China.

Published: October 2024

AI Article Synopsis

  • The study explores the creation of asymmetric microenvironments in proteins, utilizing weak bonds during folding to inspire artificial chiral materials design.
  • It reports on using chalcogen bonding to transport supramolecular chirality, focusing on specific benzochalcogenadiazole motifs that interact with amino acids to create structures with distinct chiral properties.
  • The research further demonstrates the application of these chiral motifs in directing the handedness of other compounds, leading to develop thermal chiroptical switches with tunable phosphorescent properties.

Article Abstract

The formation of asymmetric microenvironments in proteins benefits from precise transportation of chirality across multiple levels through weak bonds in the folding and assembly process, which inspires the rational design and fabrication of artificial chiral materials. Herein, the chalcogen bonding-directed precise transportation of supramolecular chirality toward multiple levels is reported to aid the fabrication of chiroptical materials. Benzochalcogenadiazole (O, S, Se) motifs are conjugated to amino acid residues, and the solid-state assemblies afforded selective supramolecular chirality with handedness depending on the kinds of chalcogen atoms and amino acids. The chalcogen-N sequence assisted by hydrogen bonding synergistically allows for the complexation with pyrene conjugated aryl carboxylic acids to give macroscopic helical structures with active circular dichroism and circularly polarized luminescence, of which handedness is precisely determined by the pristine chiral species. Then the further application of chiral benzochalcogenadiazole motifs as seeds in directing handedness of benzamide via symmetry breaking is realized. Behaving as the dopants, embedding into the matrix of benzophenone induces the room temperature phosphorescence, whereby the thermal chiroptical switch is fabricated with color-tunable phosphorescent circularly polarized luminescence. This work utilized benzochalcogenadiazole-based chiral building units to accomplish precise transportation of supramolecular chirality in coassemblies with high-fidelity, achieving flexible manipulation of chiroptical properties and macroscopic helical sense.

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Source
http://dx.doi.org/10.1002/smll.202407149DOI Listing

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