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On-surface synthesis and characterization of tetraazanonacene

Isosteric replacement of CH units of acenes by nitrogen induces significant changes in their electronic, redox, and spectroscopic properties. Here, we describe the on-surface synthesis of a nonacene analogue substituted with four nitrogen atoms on a Au(111) surface by a two-step atom manipulation, e...

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Bibliographic Details
Main Authors: Ruan, Zilin (Author) , Ye, Liping (Author) , Singh, Yogendra (Author) , Naumann, Tim (Author) , Kang, Faming (Author) , Liu, Ye (Author) , Mastalerz, Michael (Author) , Gottfried, J. Michael (Author)
Format: Article (Journal)
Language:English
Published: 10 June 2025
In: Angewandte Chemie. International edition
Year: 2025, Volume: 64, Issue: 33, Pages: 1-7
ISSN:1521-3773
DOI:10.1002/anie.202504707
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/anie.202504707
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202504707
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Author Notes:Zilin Ruan, Liping Ye, Yogendra Singh, Tim Naumann, Faming Kang, Ye Liu, Michael Mastalerz, and J. Michael Gottfried
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Summary:Isosteric replacement of CH units of acenes by nitrogen induces significant changes in their electronic, redox, and spectroscopic properties. Here, we describe the on-surface synthesis of a nonacene analogue substituted with four nitrogen atoms on a Au(111) surface by a two-step atom manipulation, employing a bis vinylene-bridged precursor synthesized in solution. The generated tetraazanonacene has been investigated by scanning tunnelling microscopy/spectroscopy (STM/STS) and noncontact atomic force microscopy (nc-AFM), combined with first-principles calculations. We found that, compared to the pristine nonacene, the electronegative nitrogen atoms lower the frontier orbitals, resulting in an increased STS transport gap of 1.49 eV. Furthermore, the formation of four pyridine-like rings induces a stronger modulation of the aromaticity in tetraazanonacene compared to substitution patterns where nitrogen atoms form pyrazine-like rings. This observation is different from the nucleus independent chemical shift investigation of previous reported tetraazaundecacene, for which a stronger open-shell character is expected. Our work provides access to the synthesis of extended azaacenes and to an understanding of their properties.
Item Description:Gesehen am 17.11.2025
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.202504707

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