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Issue 11, 2014
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Two-point halogen bonding between 3,6-dihalopyromellitic diimides

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Abstract

The syntheses of 3,6-dichloro-, -dibromo-, and -diiodopyromellitic diimides—ACl, ABr, and AI, respectively—have been achieved. X-Ray crystallography of single crystals of ACl and ABr unveils the formation of extensive halogen-bonding networks in the solid state as a consequence of interactions between the lone pairs on the carbonyl oxygen atoms with the σ-holes of the halogen atoms. Further, the solid-state superstructure of diiodopyromellitic diimide is characterised by the formation of associated halogen-π dimers. The co-crystallisation of ACl or ABr with a 1,5-diaminonaphthalene derivative DN yields co-crystals of a mixed-stack charge-transfer (CT) complex which are supported by an expansive hydrogen-bonded network in addition to halogen-bonded belts that bring adjacent mixed-stacks into association with each other. 2,6-Dimethoxynaphthalene (DO) proved to be an effective CT complement to AI, yielding solvent-free co-crystals with superstructures which are comprised of a 1 : 2 ratio of AI to DO. This dimeric halogen-bonding motif is reminiscent of the formation of hydrogen-bonded dimers between carboxylic acids.

Graphical abstract: Two-point halogen bonding between 3,6-dihalopyromellitic diimides

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Publication details

The article was received on 04 Apr 2014, accepted on 29 Jun 2014 and first published on 02 Jul 2014


Article type: Edge Article
DOI: 10.1039/C4SC00999A
Author version available: Download Author version (PDF)
Citation: Chem. Sci., 2014,5, 4242-4248
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    Two-point halogen bonding between 3,6-dihalopyromellitic diimides

    D. Cao, M. Hong, A. K. Blackburn, Z. Liu, J. M. Holcroft and J. F. Stoddart, Chem. Sci., 2014, 5, 4242
    DOI: 10.1039/C4SC00999A

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