Chiroptical Properties of Symmetric Double, Triple, and Multiple Helicenes
2021/01/07 by Tadashi Mori · 38 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Materials Science · #DNA and Nucleic Acid Chemistry #Photochromic and Fluorescence Chemistry #Synthesis and Properties of Aromatic Compounds
paper · doi:10.1021/acs.chemrev.0c01017
openalex publication_date 2021/01/07 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/27
Abstract
Helicenes have attracted considerable attention due to their inherent helical chirality and extended π-conjugation. Recently, rapid progress has been witnessed in the preparation of double, triple, quadruple, quintuple, and sextuple helicenes, where plural helicene moieties are symmetrically arranged in a single molecule. While synthetic efforts and X-ray crystallographic analyses devoted to these multiple helicenes and theoretical investigations on their isomerization and racemization behaviors have been relatively well documented and reviewed in the literature, the chiroptical properties of the multiple helicities have been somewhat overlooked. This review discourses the cumulative and systematic investigations on the chiroptical properties such as the circular dichroism (CD) and circularly polarized luminescence (CPL) of multiple helicenes. Although the number and structural variations of multiple helicenes reported to date have been fairly limited, this review overviews the current status of the chemistry of multiple helicenes from the viewpoint of chiroptical properties and provides insights into the design principle for advanced chiroptical materials through the proper arrangement of multiple helices, highlighting the impact of the molecular symmetry on the chiroptical responses.
Citations
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- Effect of π‐Electron Conjugation on the Chiroptical Properties of Helicene Carbon Nanohoops
- A Triply [5]Helicene‐Bridged (1,3,5)Cyclophane
- Solution-processed red CPL-OLEDs enabled by an exciplex-forming host and chiral helicene dopant
- Multi-responsive CPL switches of carbon dots confined in chiral metal–organic frameworks
- New advances in chiral nanographene chemistry
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- Achiral Guest-Modulated Circularly Polarized Luminescence of Chiral Macrocycles by Host–Guest Encapsulation
- Asymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes. [europepmc]
- Sulfurane [S(IV)]-Mediated Fusion of Benzynes Leads to Helical Dibenzofurans. [europepmc]
- Bottom-up supramolecular assembly in two dimensions. [europepmc]
- Challenges and opportunities for chiral covalent organic frameworks. [europepmc]
- Highly contorted superhelicene hits near-infrared circularly polarized luminescence. [europepmc]
- Cyclic arrays of five pyrenes on one rim of a planar chiral pillar[5]arene. [europepmc]
- Two-Step Synthesis, Structure, and Optical Features of a Double Hetero[7]helicene. [europepmc]
- Electrochemical synthesis of heterodehydro[7]helicenes. [europepmc]
- A pillar[5]arene-based planar chiral charge-transfer dye with enhanced circularly polarized luminescence and multiple responsive chiroptical changes. [europepmc]
- Metallophilic Interactions Drive Supramolecular Chirality Evolution and Amplify Circularly Polarized Luminescence. [europepmc]
- Helical Bilayer Nanographenes: Impact of the Helicene Length on the Structural, Electrochemical, Photophysical, and Chiroptical Properties. [europepmc]
- Construction of hexabenzocoronene-based chiral nanographenes. [europepmc]
- Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization. [europepmc]
- Helical fused 1,2:8,9-dibenzozethrene oligomers with up to 201° end-to-end twist: "one-pot" synthesis and chiral resolution. [europepmc]
- Chalcogen-doped, ( seco )-hexabenzocoronene-based nanographenes: synthesis, properties, and chalcogen extrusion conversion. [europepmc]
- Boosting quantum yields and circularly polarized luminescence of penta- and hexahelicenes by doping with two BN-groups. [europepmc]
- Understanding Aromaticity in [5]Helicene-Bridged Cyclophanes: A Comprehensive Study. [europepmc]
- Thia[ n ]helicenes with long persistent phosphorescence. [europepmc]
- Enantioselective synthesis of [4]helicenes by organocatalyzed intermolecular C-H amination. [europepmc]
- One-pot asymmetric living copolymerization-induced chiral self-assemblies and circularly polarized luminescence. [europepmc]
- Boron-containing helicenes as new generation of chiral materials: opportunities and challenges of leaving the flatland. [europepmc]
- Twenty Years of Graphene: From Pristine to Chemically Engineered Nano-Sized Flakes. [europepmc]
- Adding multiple electrons to helicenes: how they respond? [europepmc]
- Homochiral versus Racemic 2D Covalent Organic Frameworks. [europepmc]
- Quantum Chemistry Calculations of Circularly Polarized Luminescence (CPL): From Spectral Modeling to Molecular Design. [europepmc]
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