Perfluorocarbon-Hydrocarbon Self-Assembly: First Crystalline Halogen-Bonded Complex Involving Bromoperfluoroalkanes
Cryst. Growth Des. 2003, 3, 799
R. Liantonio, P. Metrangolo, T. Pilati, G. Resnati, A. Stevenazzi
Space filling representation of the crystal packing of the complex between <i>N,N,N-tetramethyl-p-phenylene-diamine and 1,8-dibromoperfluorooctane. Colours are as follows: red, bromine; blue, nitrogen; green, fluorine; grey, carbon.'>
Space filling representation of the crystal packing of the complex between N,N,N',N'-tetramethyl-p-phenylene-diamine and 1,8-dibromoperfluorooctane. Colours are as follows: red, bromine; blue, nitrogen; green, fluorine; grey, carbon.
ABSTRACT
Bromoperfluoroalkanes are here shown to drive, for the first time, the formation of halogen bonded perfluorocarbon-hydrocarbon co-crystals which are solid and stable in the air at room temperature. Specifically, the N···Br halogen bond between N,N,N?,N?-tetramethyl-p-phenylenediamine and 1,8-dibromoperfluorooctane is strong enough to control their self-assembly into one-dimensional infinite chains where the two modules alternate. The low affinity that perfluorocarbon derivatives show for hydrocarbon compounds controls the packing of these chains.