Acta Crystallographica Section B

Structural Science, Crystal Engineering and Materials

Volume 70, Part 1 (February 2014)

crystal engineering

Acta Cryst. (2014). B70, 149-156    [ doi:10.1107/S205252061302622X ]

Azobenzene-based difunctional halogen-bond donor: towards the engineering of photoresponsive co-crystals

M. Saccone, G. Terraneo, T. Pilati, G. Cavallo, A. Priimagi, P. Metrangolo and G. Resnati

Abstract: Halogen bonding is emerging as a powerful non-covalent interaction in the context of supramolecular photoresponsive materials design, particularly due to its high directionality. In order to obtain further insight into the solid-state features of halogen-bonded photoactive molecules, three halogen-bonded co-crystals containing an azobenzene-based difunctional halogen-bond donor molecule, (E)-bis(4-iodo-2,3,5,6-tetrafluorophenyl)diazene, C12F8I2N2, have been synthesized and structurally characterized by single-crystal X-ray diffraction. The crystal structure of the non-iodinated homologue (E)-bis(2,3,5,6-tetrafluorophenyl)diazene, C12H2F8N2, is also reported. It is demonstrated that the studied halogen-bond donor molecule is a reliable tecton for assembling halogen-bonded co-crystals with potential photoresponsive behaviour. The azo group is not involved in any specific intermolecular interactions in any of the co-crystals studied, which is an interesting feature in the context of enhanced photoisomerization behaviour and photoactive properties of the material systems.

CCDC references: 962602, 962603, 962604 and 962605

Keywords: photoisomerization; supramolecular photoresponsive materials design; halogen-bonded co-crystals.

hkldisplay filedownload file

Structure factor file (CIF format) (115.1 kbytes)
[ doi:10.1107/S205252061302622X/bi50161sup2.hkl ]
Contains datablock 1

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Structure factor file (CIF format) (454.0 kbytes)
[ doi:10.1107/S205252061302622X/bi50162_StOMesup3.hkl ]
Contains datablock 2_StOMe

hkldisplay filedownload file

Structure factor file (CIF format) (188.3 kbytes)
[ doi:10.1107/S205252061302622X/bi50162_bipysup4.hkl ]
Contains datablock 2_bipy

hkldisplay filedownload file

Structure factor file (CIF format) (82.0 kbytes)
[ doi:10.1107/S205252061302622X/bi50162_dmsosup5.hkl ]
Contains datablock 2_dmso


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