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Multi‐Modal Chiral Superstructures in Self‐Assembled Anthracene‐Terminal Amino Acids with Predictable and Adjustable Chiroptical Activities and Color Evolution

Zhuoer Wang, Ying‐Zhou Li, Aiyou Hao, Pengyao Xing

2020Angewandte Chemie International Edition80 citationsDOI

Abstract

Abstract Deep understanding of structure–property relationship between packing of chiral building units and their chiroptical behaviors would significantly facilitate the rational design and fabrication of the emerging chiroptical materials such as circularly polarized luminescence (CPL) emissive materials. In this paper, we unveil the universal existence of supramolecular tilt helical superstructures in self‐assembled π‐conjugated amino acid derivatives. A series of coded amino acid methyl esters were conjugated to anthracene segments at N‐terminus, which afforded 2 1 and 3 1 symmetry supramolecular tilt chirality in solid‐states. Helical assemblies enabled diversified Cotton effects and CPL performances, which were in accordance with the tilted chirality between anthracene segments. Such correlation shows fine universality, whereby the chiroptical prediction could be realized. Furthermore, on top of charge‐transfer complexation, manipulation of CPL emission colors and handedness were realized.

Topics & Concepts

Supramolecular chiralityAnthraceneChirality (physics)Supramolecular chemistryCircular dichroismLuminescenceConjugated systemRational designChemistrySelf-assemblyCircular polarizationMaterials scienceCrystallographyStereochemistryPhotochemistryCrystal structureNanotechnologyOptoelectronicsOrganic chemistryPolymerChiral symmetry breakingSymmetry breakingOpticsPhysicsQuantum mechanicsMicrostripNambu–Jona-Lasinio modelSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsSupramolecular Self-Assembly in Materials