Tetradehydrodinaphtho[10]annulene: a hitherto unknown dehydroannulene and a viable precursor to stable zethrene derivatives.

Org Lett

Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka 560-8531, Japan.

Published: September 2009

The synthesis and structural characterization of hitherto unknown tetradehydrodinaphtho[10]annulene, a hydrocarbon whose synthesis had been attempted four decades ago, was achieved for the first time. Moreover, the dinaphtho[10]annulene was transformed smoothly into stable zethrene derivatives substituted at its 7,14-positions, showing that it serves as a good reservoir of zethrene derivatives. Optical and electrochemical properties of a disubstituted zethrene derivative are also presented.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol9015942DOI Listing

Publication Analysis

Top Keywords

zethrene derivatives
12
hitherto unknown
8
stable zethrene
8
tetradehydrodinaphtho[10]annulene hitherto
4
unknown dehydroannulene
4
dehydroannulene viable
4
viable precursor
4
precursor stable
4
zethrene
4
derivatives synthesis
4

Similar Publications

Stable and twisted 5,6:12,13-dinaphthozethrene from angular π-extension.

Chem Commun (Camb)

September 2021

Institute of Molecular Plus, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin university, 92 Weijin Road, Tianjin 300072, China.

Herein, we describe a concise and efficient synthesis of an angularly extended stable zethrene derivative 1, designed to have more benzenoid rings in the closed-shell resonance form. This compound exhibited enantiomeric structures in the solid state derived from the benzo[4]helicene structure and rapid interconversion in solution. Its far-red absorption, near-infrared emission and amphoteric redox properties were also revealed.

View Article and Find Full Text PDF

Isomeric Dibenzoheptazethrenes for Air-Stable Organic Field-Effect Transistors.

Angew Chem Int Ed Engl

July 2021

Institute of Molecular Plus, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin university, 92 Weijin Road, Tianjin, 300072, China.

Singlet diradicaloids hold great potential as semiconductors for organic field-effect transistors (OFETs). However, their relative low material and device stabilities impede the practical applications. Here, to achieve balanced stability and performance, two isomeric dibenzoheptazethrene derivatives with singlet diradical character were synthesized in a concise manner.

View Article and Find Full Text PDF

One-Pot Synthesis of Boron-Doped Polycyclic Aromatic Hydrocarbons via 1,4-Boron Migration.

Angew Chem Int Ed Engl

February 2021

Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062, Dresden, Germany.

Herein, we demonstrate a novel one-pot synthetic method towards a series of boron-doped polycyclic aromatic hydrocarbons (B-PAHs, 1 a-1 o), including hitherto unknown B-doped zethrene derivatives, from ortho-aryl substituted diarylalkynes with high atom efficiency and broad substrate scopes. A reaction mechanism is proposed based on the experimental investigation together with the theoretical calculations, which involves a unique 1,4-boron migration process. The resultant benchtop-stable B-PAHs are thoroughly investigated by X-ray crystallography, cyclic voltammetry, UV/Vis absorption, and fluorescence spectroscopies.

View Article and Find Full Text PDF

Laterally extended zethrenes can be regarded as Z-shaped nanographenes with four zigzag edges, but their synthesis is very challenging. Herein, we report the successful synthesis of by far the largest zethrene molecule, a superoctazethrene (SOZ) derivative SOZ-Cl, in crystalline form. Although the parent SOZ is calculated to have a very large diradical character ( y = 81.

View Article and Find Full Text PDF

Crystal structure of 7,15-bis-(4--butyl-phen-yl)-1,9-di-methyl-hepta-zethrene.

Acta Crystallogr E Crystallogr Commun

February 2017

Advanced Institute for Materials Research, Tohoku University, Aoba-ku, Sendai 980-8577, Japan; JST, ERATO, Isobe Degenerate π-Integration Project, Aoba-ku, Sendai 980-8577, Japan; Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

The title compound, CH, , was synthesized as a derivative of hepta-zethrene bearing two methyl and two -butyl-phenyl substituents, respectively, at the 1,9- and 7,15-positions. The asymmetric unit consists of one half of the mol-ecule, which lies about an inversion centre. Albeit remotely located, the substituents contort the hepta-zethrene plane.

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!