ArticleJACS Au2021
Heterohelicenes through 1,3-Dipolar Cycloaddition of Sydnones with Arynes: Synthesis, Origins of Selectivity, and Application to pH-Triggered Chiroptical Switch with CPL Sign Reversal.
Article in JACS Au, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Tunable Synthesis of Multi-Responsive NH-Containing Helical Nanographenes With a Chiroptical Switching Function.Angewandte Chemie (International ed. in English) · 2026Article
- Enantioselective synthesis of configurationally stable [5]helicenes containing 1,2-azaborine units.Chemical science · 2026Article
- Inducing configurational stability in inherently flexible expanded heterohelicenes and unlocking stimuli-responsive chiroptical switching.Chemical science · 2026Article
- Aza[6]- and Aza[7]helicenes: Synthesis and Reversible Protonation-Induced Tuning of Photophysical and Chiroptical Properties.JACS Au · 2026Article
- Through-bondJournal of materials chemistry. C · 2026Article
- Catalytic enantioselective synthesis of azahelicenes via cascade Pictet-Spengler reaction and dehydrogenative aromatization.Nature communications · 2026Article
- Quantum Chemistry Calculations of Circularly Polarized Luminescence (CPL): From Spectral Modeling to Molecular Design.Chemical reviews · 2025Review
- Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications.Beilstein journal of organic chemistry · 2025Review
- Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers.JACS Au · 2024Article
- Helitwistacenes-Combining Lateral and Longitudinal Helicity Results in Solvent-Induced Inversion of Circularly Polarized Light.Angewandte Chemie (International ed. in English) · 2024Article
- Enantioselective synthesis of chiral quinohelicenes through sequential organocatalyzed Povarov reaction and oxidative aromatization.Nature communications · 2023Article
- A C-H activation-based enantioselective synthesis of lower carbo[n]helicenes.Nature chemistry · 2023Article
- External environment sensitive circularly polarized luminescence properties of a chiral boron difluoride complex.RSC advances · 2022Article
- Stereomutation and chiroptical bias in the kinetically controlled supramolecular polymerization of cyano-luminogens.Chemical science · 2022Article
- Mutual Monomer Orientation To Bias the Supramolecular Polymerization of [6]Helicenes and the Resulting Circularly Polarized Light and Spin Filtering Properties.Journal of the American Chemical Society · 2022Article
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Authors and funding
8 authors.
Funding
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Abstract
Regioselective access to heterohelicenes through the 1,3-dipolar cycloaddition of sydnones with arynes is described. Novel access to sydnones and poly(hetero)aromatic aryne precursors allowed the introduction of chemical diversity over multiple positions of the helical scaffolds. The origins of the unconventional regioselectivity during the cycloaddition steps was systematically investigated using density functional theory (DFT) calculations, unveiling the key features that control this reactivity, namely, face-to-face (π···π) or edge-to-face (C-H···π) interactions, primary orbital interactions and distortion from coplanarity in the transition structures (TSs) of the transformation. From the library of 24 derivatives synthesized, a pyridyl containing derivative displayed reversible, red-shifted, pH-triggered chiroptical switching properties, with CPL-sign reversal. It is found that protonation of the helicene causes a change of the angle between the electric and magnetic dipole moments related to the S
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