Bowl-to-bowl inversion of sumanene derivatives.

Chem Commun (Camb)

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, 565-0871, Japan.

Published: February 2008

AI Article Synopsis

Article Abstract

The bowl-to-bowl inversion of the non-planar bowl-shaped compounds derived from sumanene as a fullerene C3v fragment was found to be slow and tuned by a solvent, and the benzylic mono- and di-anions inverted even more slowly.

Download full-text PDF

Source
http://dx.doi.org/10.1039/b712839hDOI Listing

Publication Analysis

Top Keywords

bowl-to-bowl inversion
8
inversion sumanene
4
sumanene derivatives
4
derivatives bowl-to-bowl
4
inversion non-planar
4
non-planar bowl-shaped
4
bowl-shaped compounds
4
compounds derived
4
derived sumanene
4
sumanene fullerene
4

Similar Publications

Optical resolution chiral auxiliaries of curved subphthalocyanine aromatics.

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 PDF

Acene-Integrated Buckybowls with Near-Infrared II Absorption and over 90 % Photothermal Conversion Efficiency.

Angew Chem Int Ed Engl

January 2025

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 PDF

Bowl-Shaped Kekulene Analogues: Cycloarenes with two Five-Membered Rings.

Chemistry

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 PDF

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 PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!