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Issue 2, 2011
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Activation and de-activation of fluorine synthons by nitrogen substitution in fluorinated aza-distyrylbenzenes

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Abstract

Three derivatives of E,E-1,4-bis[2-(2,3,4,5,6-pentafluorophenyl)ethenyl]benzene, two of which bear nitrogen atoms in the ethenyl spacers, while in a third the central benzene ring is replaced by a pyrazine moiety, have been synthesized. The supramolecular structures of the resulting set of four compounds have been studied using single-crystal X-ray diffraction to gauge the influence of the position of the nitrogen atoms on the organisation of the molecules in the solid state. The crystal packing patterns were analyzed in terms of intermolecular interactions involving the fluorine and nitrogen atoms, i.e., CH⋯F, F⋯F, F⋯π and CH⋯N interactions. The analysis shows that in two of the three solid-state structures the main effect of the nitrogen atoms is an indirect one: they do not participate in intermolecular contacts themselves, but activate nearby hydrogen atoms and phenyl rings in fluorine synthons to form new interactions.

Graphical abstract: Activation and de-activation of fluorine synthons by nitrogen substitution in fluorinated aza-distyrylbenzenes

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Publication details

The article was received on 18 Jun 2010, accepted on 10 Sep 2010 and first published on 04 Oct 2010


Article type: Paper
DOI: 10.1039/C0CE00319K
Citation: CrystEngComm, 2011,13, 702-710
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    Activation and de-activation of fluorine synthons by nitrogen substitution in fluorinated aza-distyrylbenzenes

    A. Collas, R. De Borger, T. Amanova and F. Blockhuys, CrystEngComm, 2011, 13, 702
    DOI: 10.1039/C0CE00319K

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