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  Covalent C–N Bond Formation through a Surface Catalyzed Thermal Cyclodehydrogenation

Piskun, I., Blackwell, R., Jornet-Somoza, J., Zhao, F., Rubio, A., Louie, S. G., et al. (2020). Covalent C–N Bond Formation through a Surface Catalyzed Thermal Cyclodehydrogenation. Journal of the American Chemical Society, 142(8), 3696-3700. doi:10.1021/jacs.9b13507.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-E64E-1 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-6F96-5
Genre: Journal Article

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ja9b13507_si_001.pdf (Supplementary material), 10MB
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Figures S1–S8, methods and instrumentation, synthetic procedures for 2a–c, computational details, and NMR spectra (Figures S9 to S15)
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https://dx.doi.org/10.1021/jacs.9b13507 (Publisher version)
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 Creators:
Piskun, I.1, Author
Blackwell, R.1, Author
Jornet-Somoza, J.2, 3, Author              
Zhao, F.4, 5, Author
Rubio, A.2, 3, 6, Author              
Louie, S. G.4, 5, Author
Fischer, F. R.1, 5, 7, Author
Affiliations:
1Department of Chemistry, University of California, Berkeley, ou_persistent22              
2Nano-Bio Spectroscopy Group and ETSF, Universidad del País Vasco UPV/EHU, ou_persistent22              
3Theory Group, Theory Department, Max Planck Institute for the Structure and Dynamics of Matter, Max Planck Society, ou_2266715              
4Department of Physics, University of California, Berkeley, ou_persistent22              
5Materials Sciences Division, Lawrence Berkeley National Laboratory, ou_persistent22              
6Center for Computational Quantum Physics (CCQ), The Flatiron Institute, ou_persistent22              
7Kavli Energy Nano Sciences Institute at the University of California Berkeley and the Lawrence Berkeley National Laboratory, ou_persistent22              

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 Abstract: The integration of substitutional dopants at predetermined positions along the hexagonal lattice of graphene-derived polycyclic aromatic hydrocarbons is a critical tool in the design of functional electronic materials. Here, we report the unusually mild thermally induced oxidative cyclodehydrogenation of dianthryl pyrazino[2,3-g]quinoxalines to form the four covalent C–N bonds in tetraazateranthene on Au(111) and Ag(111) surfaces. Bond-resolved scanning probe microscopy, differential conductance spectroscopy, along with first-principles calculations unambiguously confirm the structural assignment. Detailed mechanistic analysis based on ab initio density functional theory calculations reveals a stepwise mechanism featuring a rate determining barrier of only ΔE = 0.6 eV, consistent with the experimentally observed reaction conditions.

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Language(s): eng - English
 Dates: 2019-12-152020-02-112020-02-26
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Method: Peer
 Identifiers: DOI: 10.1021/jacs.9b13507
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Grant ID : 795246
Funding program : Horizon 2020 (H2020)
Funding organization : European Commission (EC)

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Title: Journal of the American Chemical Society
  Other : J. Am. Chem. Soc.
  Abbreviation : JACS
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: 5 Volume / Issue: 142 (8) Sequence Number: - Start / End Page: 3696 - 3700 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870