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Doubly Linked Azulene Dimer: A Novel Non-benzenoid Isomer of Perylene.
Chemistry
January 2025
Yamaguchi University, Department of Chemistry, 753-8512, Yamaguchi, JAPAN.
We report herein the synthesis of an unprecedented isomer of perylene, dicyclohepta[cd,fg]-as-indacene bearing two phenyl groups (1-Ph) by the nickel-mediated intramolecular homocoupling of a 4,4'-biazulene derivative (2). The X-ray crystallographic analysis and theoretical calculations revealed that 1-Ph adopts a unique helically twisted geometry although the local aromaticity of azulene moieties was preserved. The double covalent linkage of the two azulene skeletons imparts significant orbital interaction, which affords near-infrared (NIR) absorption (up to 1720 nm) and remarkable redox behaviors despite its closed-shell electronic structure.
View Article and Find Full Text PDFBackground: Reducing fibrous aggregates of protein tau is a possible strategy for halting progression of Alzheimer's disease (AD). Previously we found that in vitro the D-peptide D-TLKIVWC fragments tau fibrils from AD brains (AD-tau) into benign segments, whereas its six-residue analog D-TLKIVW cannot. However, the underlying fragmentation mechanism remains unknown, preventing the further development of this type of drug candidate for AD.
View Article and Find Full Text PDFUnraveling the Atomistic Mechanism of Electrostatic Lateral Association of Peptide β-Sheet Structures and Its Role in Nanofiber Growth and Hydrogelation.
Small
January 2025
Leicester Institute for Pharmaceutical Innovation, Leicester School of Pharmacy, De Montfort University, The Gateway, Leicester, LE1 9BH, UK.
Guiding molecular assembly of peptides into rationally engineered nanostructures remains a major hurdle against the development of functional peptide-based nanomaterials. Various non-covalent interactions come into play to drive the formation and stabilization of these assemblies, of which electrostatic interactions are key. Here, the atomistic mechanisms by which electrostatic interactions contribute toward controlling self-assembly and lateral association of ultrashort β-sheet forming peptides are deciphered.
View Article and Find Full Text PDFOrganocatalytic enantioselective synthesis of double S-shaped quadruple helicene-like molecules.
Nat Commun
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Chemical Biology Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing, China.
Helicene-shaped molecules are compelling chemical structures with unique twisted helical chirality and remarkable properties. Although progress occurs in the catalytic asymmetric synthesis of helicene (-like) molecules, the enantioselective synthesis of multiple helicenes, especially four or higher helicity, is still challenging and has yet to be achieved. Herein, we report an organocatalytic [4 + 2] cycloadditions to achieve double S-shaped quadruple helicene-like molecules with high enantioselectivity (up to 96% e.
View Article and Find Full Text PDFRegioisomeric π-Extended Nanographene with Long-lived Phosphorescence Afterglow.
Angew Chem Int Ed Engl
January 2025
NCL: CSIR National Chemical Laboratory, Organic Chemistry, Dr. Homi Bhabha Road, 411008, Pune, INDIA.
The cutouts of graphene sheets, particularly those with a nonplanar topology, present vast opportunities for advancement. Even a slight deviation from the planar structure can lead to intriguing (chiro)optical features for helically twisted nanographenes. In this context, we introduce two regioisomeric π-extended nanographenes that exhibit distinct excited-state characteristics.
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