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Issue 100, 2015
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Synergistic effects of halogen bond and π–π interactions in thiophene-based building blocks

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Abstract

Although recognized as a significant force in crystal engineering, halogen bonding (XB) has been scarcely investigated in “bottom-up” approaches towards organic electronics. We report, herein, the use of a thiophene-based building block, pyridyl-thiophene (Pyr-T), to achieve an assembly driven by XB and π–π stacking interactions with iodopentafluorobenzene (IPFB). Spectroscopic and thermal analysis of the co-crystal provide indirect evidence of the assembly. The combined effects of XB and π–π stacking are confirmed experimentally via X-ray crystallography. Density functional theory (DFT) computations support experimental observations. The results of the study speak to the use of halogen bond driven self-assembly in organic electronic device application.

Graphical abstract: Synergistic effects of halogen bond and π–π interactions in thiophene-based building blocks

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The article was received on 18 Aug 2015, accepted on 21 Sep 2015 and first published on 21 Sep 2015


Article type: Paper
DOI: 10.1039/C5RA16680B
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2015,5, 82544-82548
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    Synergistic effects of halogen bond and π–π interactions in thiophene-based building blocks

    J. Wilson, J. S. Dal Williams, C. Petkovsek, P. Reves, J. W. Jurss, N. I. Hammer, G. S. Tschumper and D. L. Watkins, RSC Adv., 2015, 5, 82544
    DOI: 10.1039/C5RA16680B

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