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Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (amp;gt;1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of p-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants., Funding Agencies|European Unions Horizon research and innovation program 2D ink [664878]; Alexander von Humboldt Foundation; European Social Fund; Federal State of Saxony (ESF-Project "GRAPHD"); H-MSCA-IF program; DFG; ERC Consolidator Grant NanoSurfs [615233]; Max Planck Society; German Excellence Initiative "Center for Advancing Electronics Dresden" (cfaed); Graphene Flagship

Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (amp;gt;1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of p-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants., Funding Agencies|European Unions Horizon research and innovation program 2D ink [664878]; Alexander von Humboldt Foundation; European Social Fund; Federal State of Saxony (ESF-Project "GRAPHD"); H-MSCA-IF program; DFG; ERC Consolidator Grant NanoSurfs [615233]; Max Planck Society; German Excellence Initiative "Center for Advancing Electronics Dresden" (cfaed); Graphene Flagship

Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (amp;gt;1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of p-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants., Funding Agencies|European Unions Horizon research and innovation program 2D ink [664878]; Alexander von Humboldt Foundation; European Social Fund; Federal State of Saxony (ESF-Project "GRAPHD"); H-MSCA-IF program; DFG; ERC Consolidator Grant NanoSurfs [615233]; Max Planck Society; German Excellence Initiative "Center for Advancing Electronics Dresden" (cfaed); Graphene Flagship

Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (amp;gt;1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of p-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants., Funding Agencies|European Unions Horizon research and innovation program 2D ink [664878]; Alexander von Humboldt Foundation; European Social Fund; Federal State of Saxony (ESF-Project "GRAPHD"); H-MSCA-IF program; DFG; ERC Consolidator Grant NanoSurfs [615233]; Max Planck Society; German Excellence Initiative "Center for Advancing Electronics Dresden" (cfaed); Graphene Flagship

Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (amp;gt;1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of p-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of the central ring is indicated by optical absorption spectroscopy in conjunction with theoretical calculations. Our strategy opens up methods for chemically tailoring graphene and nanographenes, modified by antiaromatic dopants., Funding Agencies|European Unions Horizon research and innovation program 2D ink [664878]; Alexander von Humboldt Foundation; European Social Fund; Federal State of Saxony (ESF-Project "GRAPHD"); H-MSCA-IF program; DFG; ERC Consolidator Grant NanoSurfs [615233]; Max Planck Society; German Excellence Initiative "Center for Advancing Electronics Dresden" (cfaed); Graphene Flagship