Synfacts 2015; 11(3): 0259
DOI: 10.1055/s-0034-1380108
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A Rapid Route to Core Nitrogen Containing Polycyclic Aromatics

Timothy M. Swager
Myles B. Herbert
Berger R, Wagner M, Feng X, * Müllen K. * Max-Planck-Institut für Polymerforschung, Mainz and Technische Universität Dresden, Germany
Polycyclic Aromatic Azomethine Ylides: A Unique Entry to Extended Polycyclic Heteroaromatics.

Chem. Sci. 2015;
6: 436-441
Further Information

Publication History

Publication Date:
16 February 2015 (online)



The authors report a facile method to generate novel nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs) using a metal-free approach. The sequence involves a 1,3-dipolar cycloaddition of an azomethine ylide with a dipolarophile, followed by an oxidation/planarization step; it was shown that this can be efficiently performed in one pot.



The products formed are fully planar π-extended N-PAHs that have rich photophysical properties. Installing nitrogen atoms in the core of these π-extended structures has traditionally been more synthetically challenging than decorating their periphery. Accordingly, the modular nature and rapid construction of these new extended aromatic systems should enable further research into their potential applications in nanoelectronics and related fields.