Exploitation of the Menshutkin reaction for the controlled assembly of halogen bonded architectures incorporating 1,2-diiodotetrafluorobenzene and 1,3,5-triiodotrifluorobenzene

Pfrunder, Michael C., Micallef, Aaron S., Rintoul, Llewellyn, Arnold, Dennis P., Davy, Karl J. P. and McMurtrie, John (2012) Exploitation of the Menshutkin reaction for the controlled assembly of halogen bonded architectures incorporating 1,2-diiodotetrafluorobenzene and 1,3,5-triiodotrifluorobenzene. Crystal Growth and Design, 12 2: 714-724.


Author Pfrunder, Michael C.
Micallef, Aaron S.
Rintoul, Llewellyn
Arnold, Dennis P.
Davy, Karl J. P.
McMurtrie, John
Title Exploitation of the Menshutkin reaction for the controlled assembly of halogen bonded architectures incorporating 1,2-diiodotetrafluorobenzene and 1,3,5-triiodotrifluorobenzene
Journal name Crystal Growth and Design   Check publisher's open access policy
ISSN 1528-7483
1528-7505
Publication date 2012-02-01
Year available 2011
Sub-type Article (original research)
DOI 10.1021/cg201017r
Volume 12
Issue 2
Start page 714
End page 724
Total pages 11
Place of publication Washington, DC, U.S.A.
Publisher American Chemical Society
Collection year 2012
Language eng
Formatted abstract 1,4-Diazabicyclo[2.2.2]octane (DABCO) forms well-defined co-crystals with 1,2-diiodotetrafluorobenzene (1,2-DITFB), [(1,2-DITFB)2DABCO], and 1,3,5-triiodotrifluorobenzene, [(1,3,5-TITFB)2DABCO]. Both systems exhibited lower-than-expected supramolecular connectivity, which inspired a search for polymorphs in alternative crystallization solvents. In dichloromethane solution, the Menshutkin reaction was found to occur, generating chloride anions and quaternary ammonium cations through the reaction between the solvent and DABCO. The controlled in situ production of chloride ions facilitated the crystallization of new halogen bonded networks, DABCO–CH2Cl[(1,2-DITFB)Cl] (zigzag X-bonded chains) and (DABCO–CH2Cl)3[(1,3,5-TITFB)2Cl3]·CHCl3 (2D pseudo-trigonal X-bonded nets displaying Borremean entanglement), propagating with charge-assisted C–I···Cl halogen bonds. The method was found to be versatile, and substitution of DABCO with triethylamine (TEA) gave (TEA-CH2Cl)3[(1,2-DITFB)Cl3]·4(H2O) (mixed halogen bond hydrogen bond network with 2D supramolecular connectivity) and TEA-CH2Cl[(1,3,5-TITFB)Cl] (tightly packed planar trigonal nets). The co-crystals were typically produced in high yield and purity with relatively predictable supramolecular topology, particularly with respect to the connectivity of the iodobenzene molecules. The potential to use this synthetic methodology for crystal engineering of halogen bonded architectures is demonstrated and discussed.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ
Additional Notes Published: December 20, 2011. Published as part of the Crystal Growth & Design virtual special issue on Halogen Bonding in Crystal Engineering: Fundamentals and Applications.

 
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Created: Wed, 25 Jan 2012, 09:28:56 EST by Sandrine Ducrot on behalf of Aust Institute for Bioengineering & Nanotechnology