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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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Supplementary files

Article information


Submitted
18 Aug 2015
Accepted
21 Sep 2015
First published
21 Sep 2015

RSC Adv., 2015,5, 82544-82548
Article type
Paper
Author version available

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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