Issue 1, 2015

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2015,6, 436-441

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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