Functionalized surface-confined pores: Guest binding directed by lateral noncovalent interactions at the solid-liquid interface

Kazukuni Tahara*, Keisuke Katayama, Matthew Oliver Blunt, Kohei Iritani, Steven De Feyter, Tobe Yoshito

*Corresponding author for this work

Research output: Contribution to journalArticle

31 Scopus citations


We present here the construction of self-assembled two-dimensional (2D) molecular networks that contain pores equipped with functional groups that promote guest-specific binding at the liquid/solid interface. For this purpose, a dehydrobenzo[12]annulene (DBA) derivative, DBA-F, having perfluoroalkyl groups at the end of the three alternating alkoxy chains connected by para-phenylene linkers was synthesized. For comparison DBA-H, having the same carbon backbone without fluorine substituents, was also prepared. STM observations revealed that these molecules formed porous 2D networks whose pores were decorated with either fluoroalkane or simple alkane perimeters. Hexakis(phenylethynyl)benzene, HPEB, and its octadecafluoro derivative, HPEB-F surrounded by 18 fluorine atoms, were employed as planar guest molecules of suitable size. The fluoroalkane-lined pores present in the network of DBA-F exhibited good binding ability toward both guest molecules via fluorophilicity and electrostatic interaction, respectively. In contrast the binding ability of the alkane-lined pore of the network of DBA-H for the fluorinated guest HPEB-F was poor as a result of weaker electrostatic interaction. Interestingly, with HPEB as a guest, this network underwent a periodical structural deformation through an induced-fit mechanism to form a superlattice structure consisting of free and occupied pores. These observations are discussed based on modeling experiments using molecular mechanics and quantum chemical methods to elucidate the roles of lateral noncovalent interactions and size matching between the pore and the guest molecules used for 2D guest binding.

Original languageEnglish
Pages (from-to)8683-8694
Number of pages12
JournalACS Nano
Issue number8
StatePublished - 1 Jan 2014


  • fluorophilicity
  • porous network
  • scanning tunneling microscopy
  • self-assembly
  • solid-liquid interface

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