Pinning-down molecules in their self-assemblies with multiple weak hydrogen bonds of CH⋯F and CH⋯N

Xin Jin, Jacob R. Cramer, Qi Wei Chen, Hai Lin Liang, Jian Shang, Xiang Shao, Wei Chen, Guo Qin Xu, Kurt V. Gothelf*, Kai Wu

*Corresponding author for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Abstract

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.

Original languageEnglish
JournalChinese Chemical Letters
Volume28
Issue3
Pages (from-to)525-530
Number of pages6
ISSN1001-8417
DOIs
Publication statusPublished - 2017

Keywords

  • Fluorinated pyridyl molecules
  • Grouped hydrogen bonds
  • Molecular design
  • Molecular self-assembly
  • Scanning tunneling microscopy

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