C-H...F hydrogen bonding: the origin of the self-assemblies of bis(2,2'-difluoro-1,3,2-dioxaborine)

Langmuir : the ACS Journal of Surfaces and Colloids
Dirk RohdeLi-Jun Wan

Abstract

The effect of the molecular structure on the self-assembly of specially designed two-core 1,3,2-dioxaborines has been studied with various techniques. It was found that the molecules spontaneously adsorbed on HOPG surfaces and self-organized into well-ordered two-dimensional (2D) monolayers. The structural details of the 2D assemblies were investigated by scanning tunneling microscopy (STM). From X-ray analysis of the corresponding three-dimensional (3D) crystal and from theoretical calculation, we were able to reveal the driving force behind the specific self-assembly. The C-H...F hydrogen bonding between the ortho carbon of the phenyl ring and the fluorine of the BF2 group plays an important role in the formation of the adlayers. The different electron affinities and geometries of the molecules affect the intermolecular interactions which further lead to different properties in the bulk materials.

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Citations

Apr 1, 2009·Journal of the American Chemical Society·Ki-Young KwonLudwig Bartels
Mar 19, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Pierre-Henri LanoëChantal Andraud
Nov 1, 2008·Proceedings of the National Academy of Sciences of the United States of America·Qing ChenJin-Long Yang
Jan 30, 2010·Journal of the American Chemical Society·Guoqing ZhangCassandra L Fraser
Oct 11, 2008·The Journal of Organic Chemistry·Atsushi NagaiYoshiki Chujo
Aug 28, 2009·The Journal of Physical Chemistry. B·Yunxiang LuWeiliang Zhu
Mar 30, 2012·Inorganic Chemistry·Eva M López-VidalJosé M Quintela

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