Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes 2 were straightforwardly prepared in around 20% yield from 9,10-diarylphenanthrenes 3 by palladium-catalyzed intramolecular arylations. The bowl-to-bowl inversion barrier for buckybowl 2-iPr is predicted to be approximately 7 kcal mol(-1) based on density functional theory calculations and this value is consistent with the results of a variable-temperature (1)H-NMR study.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1039/c0cc01730b | DOI Listing |
Chem Sci
November 2024
Department of Organic Chemistry, Universidad Autónoma de Madrid Madrid 28049 Spain
Chiral conjugated materials with curved topologies hold significant promise for advanced optoelectronic applications. Among these, bowl-shaped subphthalocyanine (SubPc) aromatics are particularly noteworthy due to their superb optoelectronic properties and synthetic versatility. Despite their potential, the development and application of inherently chiral SubPcs as functional materials have been hampered by the scalability and feasibility limitations of current high-performance liquid chromatography methods.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology, Beijing, 100029, P. R. China.
Tetracene and pentacene are large, promising building blocks for construction of complex molecular nanocarbons due to their extraordinary photophysical and electronic properties. Herein, two acene-integrated buckybowls, composed of two rows of tetracenes and pentacenes fused through s-indacene unit at the zigzag edges, have been synthesized and characterized. Compared to parent tetracene and pentacene, the buckybowls are extremely stable and show much smaller electrochemical band gaps.
View Article and Find Full Text PDFChemistry
August 2024
Department of Physical Science and Materials Engineering, Iwate University, 4-3-5 Ueda, Morioka, 020-8551, Japan.
Kekulene, a cycloarene composed of 12 fused benzene rings in a circular arrangement, exhibits a highly planar and robust structure. Kekulene has been the subject of investigation into its aromaticity and electronic structure, particularly in relation to the cyclic benzenoid. We have successfully synthesized novel bowl-shaped kekulene analogues with five-membered rings incorporated into the kekulene structure.
View Article and Find Full Text PDFChem Sci
January 2024
Institut für Organische Chemie, Universität Würzburg Am Hubland 97074 Würzburg Germany
Corannulene is known to undergo a fast bowl-to-bowl inversion at r.t. a planar transition structure (TS).
View Article and Find Full Text PDFChem Sci
October 2023
Beijing Advanced Innovation Center for Soft Matter Science and Engineering, Beijing University of Chemical Technology Beijing 100029 P. R. China
Here we report the synthesis of a novel buckybowl (7) with a high bowl-to-bowl inversion barrier (Δ = 38 kcal mol), which renders the rate of inversion slow enough at room temperature to establish two chiral polycyclic aromatic hydrocarbons (PAHs). By strategic fusion of eight-membered rings to the rim of 7, the chiral hybrids 8 and 9 are synthesized and display helicity and positive and negative curvature, allowing the enantiomers to be configurationally stable and their chiroptical properties are thoroughly examined. Computational and experimental studies reveal the enantiomerization mechanisms for the chiral hybrids and demonstrate that the eight-membered ring strongly affects the conformational stability.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!