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Twofold 6π-Electrocyclization as a Route Toward Multi-Heteroatom-Doped Nanographenes Built on a 1,4-Dihydropyrrolo[3,2-b]pyrrole Core.
Chemistry
November 2024
Institute of Organic Chemistry of Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
Here we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such as benzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction.
View Article and Find Full Text PDF[5]Helicene Based π-Conjugated Macrocycles with Persistent Figure-Eight and Möbius Shapes: Efficient Synthesis, Chiral Resolution and Bright Circularly Polarized Luminescence.
Angew Chem Int Ed Engl
October 2024
Department of Chemistry, National University of Singapore 3 Science Drive 3, Singapore, 117543, Singapore.
π-Conjugated chiral shape-persistent molecular nanocarbons hold great potential as chiroptical materials, though their synthesis remains a considerable challenge. Here, we present a simple approach using Suzuki coupling of a [5]helicene building block with various aromatic units, enabling the one-pot synthesis of a series of chiral macrocycles with persistent figure-eight and Möbius shapes. Single-crystal structures of 7 compounds were solved, and 22 enantiomers were separated by preparative chiral HPLC.
View Article and Find Full Text PDFPerylene-Embedded Helical Nanographenes with Emission up to 1010 nm: Synthesis, Structures, and Chiroptical Properties.
Angew Chem Int Ed Engl
January 2025
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Singapore.
Near-infrared (NIR) circularly polarized absorbing or emitting materials offer distinct advantages over their visible-light counterparts and have attracted considerable interest across various fields. Materials exhibiting NIR chiroptical properties with high fluorescence quantum yields (Φ) are particularly rare. In this study, we report the synthesis of a series of helical nanographenes (1, 2, 3, and 4), where perylene is fused with one to four hexa-peri-hexabenzocoronene (sub) units by a strategy involving Diels-Alder cycloaddition followed by a Scholl reaction.
View Article and Find Full Text PDFStereocontrolled Synthesis of Chiral Helicene-Indenido ansa- and Half-Sandwich Metal Complexes and Their Use in Catalysis.
Angew Chem Int Ed Engl
January 2025
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 542/2, 160 00, Prague 6, Czech Republic.
Article Synopsis
- Recent advancements in creating nonplanar chiral aromatics, like helicenes, have not yet translated into the development of their transition metal complexes for catalytic applications.
- This study successfully synthesized enantio- and diastereopure oxa[6]- and oxa[7]helicene-indene half-sandwich RhI and RhIII complexes, as well as a FeII complex, showcasing their potential in catalysis.
- The research demonstrated the use of oxahelicene-indenido RhIII complexes in enantioselective C-H arylation reactions, yielding axially chiral biaryls with excellent selectivity and confirming an innovative chirality transfer process.
Syntheses, Structural Analyses, and Properties of Condensed Arenes with Multihelicity.
Org Lett
September 2024
Department of Chemistry, National Cheng Kung University, Tainan 70101, Taiwan.
A -symmetric hexapole helicene (HH) and a -symmetric dodecapole helicene (DH) were prepared, and their three-dimensional structures were verified by X-ray crystallography and density functional theory calculations. The molecular geometries and local helical configurations of their most stable diastereomers were correctly predicted by arranging suitable conformations of the peripheral aryl rings. Importantly, the outermost three [5]helicenes with a consistent configuration in DH were observed to increase the thermostability, enantiomerization barrier (Δ = 40.
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