Issue 1, 2015

Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state

Abstract

Attempted cocrystallisation of brominated and iodinated octafluoroazobenzene derivatives with morpholine led to the exhaustive replacement of fluorine substituents that are in ortho-positions to the azobenzene with sterically demanding morpholine groups. The resulting molecules exhibit a highly unusual strained conformation of the azobenzene unit, in which the terminal phenyl rings adopt a mutually nearly completely orthogonal orientation. Substitution of ortho-fluorine groups with N-morpholine fragments provides molecules with active halogen bond donor and acceptor sites that guide the molecular self-assembly in the solid state towards the formation of polymeric halogen-bonded chains.

Graphical abstract: Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state

Supplementary files

Article information

Article type
Paper
Submitted
13 Jun 2014
Accepted
19 Sep 2014
First published
22 Sep 2014

CrystEngComm, 2015,17, 73-80

Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state

O. S. Bushuyev, D. Tan, C. J. Barrett and T. Friščić, CrystEngComm, 2015, 17, 73 DOI: 10.1039/C4CE01216J

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