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Issue 1, 2015
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Fluorinated azobenzenes with highly strained geometries for halogen bond-driven self-assembly in the solid state

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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

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Publication details

The article was received on 13 Jun 2014, accepted on 19 Sep 2014 and first published on 22 Sep 2014


Article type: Paper
DOI: 10.1039/C4CE01216J
Citation: CrystEngComm, 2015,17, 73-80
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    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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