Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Co-Crystallisation of 1,4-Diiodotetrafluorobenzene with Three Different Symmetric Dipyridylacetylacetone Isomers Produces Four Halogen-Bonded Architectures*

Joshua J. Brown A , Aidan J. Brock A , Michael C. Pfrunder A , Julia P. Sarju B , Abigail Z. Perry B , Adrian C. Whitwood B , Duncan W. Bruce B , John C. McMurtrie C D and Jack K. Clegg A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, Qld 4072, Australia.

B Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

C School of Chemistry, Physics and Mechanical Engineering, Faculty of Science and Engineering, Queensland University of Technology, GPO Box 2434, Brisbane, Qld 4001, Australia.

D Corresponding authors. Email: j.mcmurtrie@qut.edu.au; j.clegg@uq.edu.au

Australian Journal of Chemistry 70(5) 594-600 https://doi.org/10.1071/CH16673
Submitted: 1 December 2016  Accepted: 20 January 2017   Published: 13 February 2017

Abstract

The co-crystallisation behaviour of three symmetrical dipyridylacetylacetone ligands (1,3-di(2-pyridyl)-1,3-propanedione (o-bppdH), 1,3-di(3-pyridyl)-1,3-propanedione (m-bppdH), and 1,3-di(4-pyridyl)-1,3-propanedione (p-bppdH)), with the linear halogen-bond donor 1,4-diiodotetrafluorobenzene (1,4-DITFB) has been investigated. The reaction of these components under ambient conditions in a 1 : 1 stoichiometry produced four halogen-bonded assemblies ([o-bppdH·1,4-DITFB, [m-bppdH·1,4-DITFB], [2(m-bppdH)·1,4-DITFB], and [p-bppdH·1,4-DITFB]). The combination of multiple supramolecular interactions including halogen bonding, hydrogen bonding, and π-stacking produces a range of supramolecular architectures, including one-, two-, and three-dimensional motifs. The crystal structure of m-bppdH is also reported.


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