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Heterocyclic Ring‐Opening of Nanographene on Au(111)
Author(s) -
Sun Kewei,
Sugawara Kazuma,
Lyalin Andrey,
Ishigaki Yusuke,
Uosaki Kohei,
Taketsugu Tetsuya,
Suzuki Takanori,
Kawai Shigeki
Publication year - 2021
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.202017137
Subject(s) - intramolecular force , pyrazine , ring (chemistry) , dehydrogenation , molecule , chemistry , scanning tunneling microscope , quinoline , hydrogen bond , crystallography , density functional theory , carbon fibers , nitrogen , triple bond , photochemistry , materials science , computational chemistry , polymer chemistry , stereochemistry , organic chemistry , nanotechnology , double bond , catalysis , composite number , composite material
Cyclo‐dehydrogenation is of importance to induce the planarization of molecules on noble surfaces upon annealing. In contrast to a number of successful syntheses of polycyclic aromatic hydrocarbons by forming carbon–carbon bonds, it is still rare to conduct conjugation and cleavage of carbon–nitrogen bonds in molecules. Here, we present a systematic transformation of the C−N bonds in11,11,12,12‐tetraphenyl‐1,4,5,8‐tetraazaanthraquinodimethane as well as three other derivatives on Au(111). With bond‐resolved scanning tunneling microscopy, we discovered novel the “heterocyclic segregation” reaction of one pyrazine ring with two nitrogen atoms to form two quinoline rings with one nitrogen each. Density functional theory calculations showed that the intramolecular ring‐forming and ‐opening of N‐heterocycles are strongly affected by the initial hydrogen–substrate interaction.