Halogen bonding in diaza-triisopropylsilyl-tetracene crystals?
Four halogenated triisopropylsilylethynyl (TIPS)-tetracene derivatives were synthesized, their single crystal structures and optical and electronic properties were examined. Both, diiodo-TIPS-diazatetracene and dibromo-TIPSdiazatetracene showed herringbone arrangements, in which the halogen atoms ar...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
September 4, 2014
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| In: |
Crystal growth & design
Year: 2014, Volume: 14, Issue: 11, Pages: 5962-5965 |
| ISSN: | 1528-7505 |
| DOI: | 10.1021/cg5011538 |
| Online Access: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/cg5011538 Verlag, lizenzpflichtig, Volltext: https://pubs.acs.org/doi/10.1021/cg5011538 
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| Author Notes: | Michael Porz, Frank Rominger, and Uwe H.F. Bunz |
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| 520 | |a Four halogenated triisopropylsilylethynyl (TIPS)-tetracene derivatives were synthesized, their single crystal structures and optical and electronic properties were examined. Both, diiodo-TIPS-diazatetracene and dibromo-TIPSdiazatetracene showed herringbone arrangements, in which the halogen atoms are directed toward the nitrogen atoms of a neighboring molecule with slightly lower distances than the van der Waals radii between halogen and nitrogen atoms. Computations of the electrostatic potentials showed the availability and the strength of σ holes, so that we assume a weak halogen−nitrogen bonding. Tribromo-TIPS-diazatetracene delivered a 2D-brick wall structure with no sign of a halogen bonding. Dibromo-TIPS-tetracene crystallized neither in a herringbone nor in a brick wall motif. These results show that for halogenated azaacenes at least weak halogen−nitrogen interactions exist. | ||
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