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Control of a two-dimensional molecular structure by cooperative halogen and hydrogen bonds

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Title: Control of a two-dimensional molecular structure by cooperative halogen and hydrogen bonds
Authors: Yasuda, Satoshi Browse this author →KAKEN DB
Furuya, Atom Browse this author
Murakoshi, Kei Browse this author →KAKEN DB
Issue Date: 30-Oct-2014
Publisher: Royal Society of Chemistry
Journal Title: RSC advances
Volume: 4
Issue: 102
Start Page: 58567
End Page: 58572
Publisher DOI: 10.1039/c4ra10235e
Abstract: The cooperative effect of hydrogen and halogen bonds on the two-dimensional (2D) molecular arrangement on highly oriented pyrolytic graphite (HOPG) was studied by scanning tunneling microscopy. The terephthalic acid (TPA) molecule, which has two carboxyl groups attached at the para positions of a benzene ring, formed a one-dimensional (1D) linear non-covalent network structure on HOPG by hydrogen bonds between the carboxyl groups of neighboring molecules. However, unlike the TPA molecule, Br substituted TPA molecules were found to form different non-covalent network structures. Owing to Br center dot center dot center dot O halogen and hydrogen bonds, bromo-substituted TPA (2-bromoterephthalic acid) formed a 1D ladder-like non-covalent network structure, whereas dibromo-substituted TPA (2,5-dibromoterephthalic acid) formed a 2D non-covalent lattice network on HOPG. These results strongly indicate that Br center dot center dot center dot O halogen bonds significantly contribute to determine the molecular assembly as well as hydrogen bonds for molecules containing bromine groups and hydrogen bonding groups. These results provided deep fundamental insight into the cooperative effect of halogen and hydrogen bonds in 2D molecular assemblies. In addition, we have demonstrated that these interactive bonds are promising for the precise design of 2D molecular architectures.
Type: article (author version)
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 保田 諭

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