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Issue 65, 2019
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An axially chiral 1,1′-biazulene and its π-extended derivative: synthesis, structures and properties

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Abstract

Chiral organic π-conjugated molecules have been intensively investigated in the fields of chiral electronic materials and devices. Herein we report a new motif for an axially chiral 1,1′-biazulene and its π-extended derivative, in which biphenyl was annulated by the electron-rich five-membered-ring of the azulene moiety. These two compounds were unexpectedly synthesized from 2-terphenyl azulene by stepwise intermolecular and intramolecular oxidative C–H/C–H couplings. X-ray diffraction analysis revealed that the crystals of both compounds contain a pair of enantiomers. Furthermore, the axially chiral 1,1′-biazulene derivatives were successfully separated into enantiomers that exhibited clear mirror-image circular dichroism spectra up to the near-infrared region.

Graphical abstract: An axially chiral 1,1′-biazulene and its π-extended derivative: synthesis, structures and properties

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Article information


Submitted
07 May 2019
Accepted
10 Jul 2019
First published
11 Jul 2019

Chem. Commun., 2019,55, 9606-9609
Article type
Communication
Author version available

An axially chiral 1,1′-biazulene and its π-extended derivative: synthesis, structures and properties

Chaolumen, H. Ito and K. Itami, Chem. Commun., 2019, 55, 9606
DOI: 10.1039/C9CC03510A

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