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J Am Chem Soc. 2008 Aug 20;130(33):10840-1. doi: 10.1021/ja801925q. Epub 2008 Jul 24.

Two dimensional chiral networks emerging from the aryl-F...H hydrogen-bond-driven self-assembly of partially fluorinated rigid molecular structures.

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  • 1Physikalisches Institut, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Str. 10, 48149 Münster, Germany.

Abstract

Self-assembly of the partially fluorinated rigid molecules physisorbed at solution/graphite interface has been investigated by scanning tunneling microscopy. Upon adsorption, both the branched star-shaped compound 1 and the angulate rod 2 compromising diacetylene and acetylene interlinked benzene and pentafluorobezene formed two-dimensional chiral porous networks. The spontaneous formation of these architectures is likely attributed to the two effects: the compensation of the dipole moments of the branches and the formation of Ar-H...F hydrogen bonds. These results demonstrate that the immobilization of molecules at the liquid/solid interface can be driven by these weak intermolecular interactions instead of van der Waals interactions between alkyl chains and substrate.

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