Citation: Jin Xin, Cramer Jacob R., Chen Qi-Wei, Liang Hai-Lin, Shang Jian, Shao Xiang, Chen Wei, Xu Guo-Qin, Gothelf Kurt V., Wu Kai. Pinning-down molecules in their self-assemblies with multiple weak hydrogen bonds of C-H…F and C-H…N[J]. Chinese Chemical Letters, ;2017, 28(3): 525-530. doi: 10.1016/j.cclet.2016.11.007 shu

Pinning-down molecules in their self-assemblies with multiple weak hydrogen bonds of C-H…F and C-H…N

Jin Xin ^a ,
Cramer Jacob R. ^b ,
Chen Qi-Wei ^a ,
Liang Hai-Lin ^a ,
Shang Jian ^a ,
Shao Xiang ^c ,
Chen Wei ^d,e ,
Xu Guo-Qin ^d,e ,
Gothelf Kurt V. ^b,, ,
Wu Kai ^a,e,,

a.
BNLMS, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
b.
Danish-Chinese Centre for Self-Assembly and Function of Molecular Nanostructures on Surfaces at iNANO, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark
c.
Department of Chemical Physics, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China
d.
Department of Chemistry, National University of Singapore, 117543, Singapore
e.
SPURc, 1 CREATE Way, #15-01, CREATE Tower, 138602, Singapore

Corresponding author: Gothelf Kurt V., kvg@chem.au.dk Wu Kai, kaiwu@pku.edu.cn
Received Date: 15 June 2016
Revised Date: 28 October 2016
Accepted Date: 28 October 2016
Available Online: 9 March 2016

Figures(5)

Two-dimensional self-assemblies of four partially fluorinated molecules, 1, 4-bis (2, 6-difluoropyridin-4-yl) benzene, 4, 4'-bis (2, 6-difluoropyridin-4-yl)-1, 1'-biphenyl, 4, 4'-bis (2, 6-difluoropyridin-4-yl)-1, 1':4', 1"-terphenyl and 4, 4'-bis (2, 6-difluoropyridin-3-yl)-1, 1'-biphenyl, involving weak intermolecular C-H…F and C-H…N hydrogen bonds were systematically investigated on Au (111) with low-temperature scanning tunneling microscopy. The inter-molecular connecting modes and binding sites were closely related to the backbones of the building blocks, i.e., the molecule length determines its binding sites with neighboring molecules in the assemblies while the attaching positions of the N and F atoms dictate its approaching and docking angles. The experimental results demonstrate that multiple weak hydrogen bonds such as C-H…F and C-H…N can be efficiently applied to tune the molecular orientations and the self-assembly structures accordingly.
- Fluorinated pyridyl molecules,
- Grouped hydrogen bonds,
- Molecular self-assembly,
- Molecular design,
- Scanning tunneling microscopy
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