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Issue 1, 2015
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Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics

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Abstract

Based on polycyclic aromatic azomethine ylides (PAMYs), a metal-free “cycloaddition-planarization-sequence” is proposed, providing a unique entry to extended nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). This method is highly versatile, as the structure of unprecedented N-PAHs can be tailored by the dipolarophile in the crucial 1,3-cycloaddition-reaction. Linear, as well as five- and six-membered cyclic dipolarophiles are successfully used. The geometric and optoelectronic nature of N-PAHs are investigated by UV-vis absorption and single crystal structure analysis. Remarkably, the newly synthesized N-PAHs demonstrate varying absorption profiles, covering the whole visible light range with rich photophysical properties, for example, fluorescent quantum yields up to 54%.

Graphical abstract: Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics

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Supplementary files

Article information


Submitted
10 Sep 2014
Accepted
21 Oct 2014
First published
22 Oct 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 436-441
Article type
Edge Article

Polycyclic aromatic azomethine ylides: a unique entry to extended polycyclic heteroaromatics

R. Berger, M. Wagner, X. Feng and K. Müllen, Chem. Sci., 2015, 6, 436
DOI: 10.1039/C4SC02793K

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