ArticleAngewandte Chemie (International ed. in English)2021
Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Bridging [8]cyclo-Chemical science · 2026Article
- TetrahedralJACS Au · 2026Article
- Streamlined synthesis of functionalized dibenzo[RSC advances · 2026Article
- Modular synthesis of benzothiophene-fused pentalenes reveals substituent-dependent antiaromaticity.Chemical science · 2026Article
- Synthesis of Enantiopure [3]Cyclorubicenes.Angewandte Chemie (International ed. in English) · 2026Article
- How do Nanohoops Exercise Their Strain in [5]Helicene Racemization?The Journal of organic chemistry · 2025Article
- Size and Geometry Impact the Chiroptical Properties of Double Nanohoops.Journal of the American Chemical Society · 2025Article
- Cycloparaazine, a full-azine carbon nanoring.Nature communications · 2025Article
- Synthesis and crystal structure of 5,10-bis-(phenyl-sulfon-yl)tetra-hydro-dibenzo-penta-lene.Acta crystallographica. Section E, Crystallographic communications · 2025Article
- Recent advances in supramolecular fullerene chemistry.Chemical Society reviews · 2024Review
- Circularly Polarized Luminescence in a Möbius Helicene Carbon Nanohoop.Angewandte Chemie (International ed. in English) · 2022Article
- Enantiopure nanohoops through racemic resolution of diketo[Chemical science · 2021Article
- Conjugated Nanohoops Incorporating Donor, Acceptor, Hetero- or Polycyclic Aromatics.Angewandte Chemie (International ed. in English) · 2021Review
- Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis.Angewandte Chemie (International ed. in English) · 2021Article
- Asymmetric synthesis, structures, and chiroptical properties of helical cycloparaphenylenes.Chemical science · 2021Article
- Cations and Anions of Dibenzo[a,e]pentalene and Reduction of a Dibenzo[a,e]pentalenophane.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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7 authors.
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Abstract
Conjugated nanohoops allow to investigate the effect of radial conjugation and bending on the involved π-systems. They can possess unexpected optoelectronic properties and their radially oriented π-system makes them attractive for host-guest chemistry. Bending the π-subsystems can lead to chiral hoops. Herein, we report the stereoselective synthesis of two enantiomers of chiral conjugated nanohoops by incorporating dibenzo[a,e]pentalenes (DBPs), which are generated in the last synthetic step from enantiomerically pure diketone precursors. Owing to its bent shape, this diketone unit was used as the only bent precursor and novel "corner unit" in the synthesis of the hoops. The [6]DBP[4]Ph-hoops contain six antiaromatic DBP units and four bridging phenylene groups. The small HOMO-LUMO gap and ambipolar electrochemical character of the DBP units is reflected in the optoelectronic properties of the hoop. Electronic circular dichroism spectra and MD simulations showed that the chiral hoop did not racemize even when heated to 110 °C. Due to its large diameter, it was able to accommodate two C60 molecules, as binding studies indicate.
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