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On‐Surface Assembly of Hydrogen‐ and Halogen‐Bonded Supramolecular Graphyne‐Like Networks
Author(s) -
Yang Zechao,
Fromm Lukas,
Sander Tim,
Gebhardt Julian,
Schaub Tobias A.,
Görling Andreas,
Kivala Milan,
Maier Sabine
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201916708
Subject(s) - synthon , graphyne , supramolecular chemistry , hydrogen bond , halogen bond , halogen , crystallography , scanning tunneling microscope , density functional theory , triazine , materials science , chemistry , nanotechnology , molecule , computational chemistry , stereochemistry , polymer chemistry , organic chemistry , crystal structure , alkyl
Demonstrated here is a supramolecular approach to fabricate highly ordered monolayered hydrogen‐ and halogen‐bonded graphyne‐like two‐dimensional (2D) materials from triethynyltriazine derivatives on Au(111) and Ag(111). The 2D networks are stabilized by N⋅⋅⋅H−C(sp) bonds and N⋅⋅⋅Br−C(sp) bonds to the triazine core. The structural properties and the binding energies of the supramolecular graphynes have been investigated by scanning tunneling microscopy in combination with density‐functional theory calculations. It is revealed that the N⋅⋅⋅Br−C(sp) bonds lead to significantly stronger bonded networks compared to the hydrogen‐bonded networks. A systematic analysis of the binding energies of triethynyltriazine and triethynylbenzene derivatives further demonstrates that the X 3 ‐synthon, which is commonly observed for bromobenzene derivatives, is weaker than the X 6 ‐synthon for our bromotriethynyl derivatives.