Nanographenes as electron-deficient cores of donor-acceptor systems

Nature Communications
Yu-Min LiuKlaus Müllen

Abstract

Conjugation of nanographenes (NGs) with electro-active molecules can establish donor-acceptor π-systems in which the former generally serve as the electron-donating moieties due to their electronic-rich nature. In contrast, here we report a series of reversed donor-acceptor structures are obtained by C-N coupling of electron-deficient perchlorinated NGs with electron-rich anilines. Selective amination at the vertexes of the NGs is unambiguously shown through X-ray crystallography. By varying the donating ability of the anilino groups, the optical and assembly properties of donor-acceptor NGs can be finely modulated. The electron-deficient concave core of the resulting conjugates can host electron-rich guest molecules by intermolecular donor-acceptor interactions and gives rise to charge-transfer supramolecular architectures.

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Citations

Jul 22, 2019·Angewandte Chemie·Yu-Min LiuYuan-Zhi Tan
Jun 6, 2019·Angewandte Chemie·Ruth DorelAlexander M Haydl
Apr 8, 2020·Beilstein Journal of Organic Chemistry·Mai NagaseKenichiro Itami
Jul 21, 2021·Journal of the American Chemical Society·Patricia Izquierdo-GarcíaNazario Martín
Jul 6, 2021·Journal of the American Chemical Society·Enquan JinAkimitsu Narita
Sep 26, 2019·ACS Omega·Frédéric LiretteJean-François Morin

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Methods Mentioned

BETA
X-ray
NMR

Software Mentioned

Olex2
XT
Gaussian
XL
SHELX
CPCM

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