open access

https://hdl.handle.net/2115/60148

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

英語

2014-10-30

Royal Society of Chemistry

RSC advances

4(102)

58567-58572

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.

学術雑誌論文

Accepted Manuscript

2046-2069