Phosphorescent co-crystal assembled by 1,4-diiodotetrafluorobenzene with carbazole based on C–I⋯π halogen bonding

1,4-diiodotetrafluorobenzene (1,4-DITFB) is an excellent halogen bonding donor and is used to assemble an organic phosphorescent co-crystal with carbazole in which 1,4-DITFB is expected to act as a functional synthon, the cement to link carbazole molecules by halogen bonding and heavy atom perturber...

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Bibliographic Details
Published in:Journal of materials chemistry 2012-03, Vol.22 (12), p.5336-5343
Main Authors: Gao, Hai Yue, Shen, Qian Jin, Zhao, Xiao Ran, Yan, Xiao Qing, Pang, Xue, Jin, Wei Jun
Format: Article
Language:English
Subjects:
Bonding
Carbazoles
Chains
Ethyl alcohol
Halogens
Nanostructure
Stacking
Three dimensional
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Summary:1,4-diiodotetrafluorobenzene (1,4-DITFB) is an excellent halogen bonding donor and is used to assemble an organic phosphorescent co-crystal with carbazole in which 1,4-DITFB is expected to act as a functional synthon, the cement to link carbazole molecules by halogen bonding and heavy atom perturber to enhance phosphorescence of the emitter carbazole by spin-orbital coupling. The XRD reveals that the stoichiometry of (2 : 1) between 1,4-DITFB and carbazole occurs. An infinite chain is constructed by the C-I... pi halogen bonding and the pi ... pi stacking of edge to edge between two 1,4-DITFB molecules is significant in maintaining stability of the 1D infinite chain. The inter-chain bonding includes C-H...I hydrogen bonding, H...F or F...F contacts to extend the infinite chain to 3D structure. The calculated halogen bonding energy is ca. 23.0 kJ mol super(-1) based on the single crystal structure, indicating a strong halogen bonding. The co-crystal also is well characterized by powder XRD, FT-IR, Raman, and solid super(19)F NMR spectroscopy. Moreover, the co-crystal as suspension microparticles can be very easily assembled in water by dropping water into an ethanol solution of 1,4-DITFB and carbazole. The C-I... pi halogen bonding of 1,4-DITFB with carbazole should be instructive to develop some phosphorescent nano- or micro-materials.
ISSN:0959-9428
1364-5501
DOI:10.1039/c2jm16257a