Beyond p-hexaphenylenes: synthesis of unsubstituted p-nonaphenylene by a precursor protocol
The synthesis of unsubstituted oligo-para-phenylenes (OPP) exceeding para-hexaphenylene—in the literature often referred to as p-sexiphenyl—has long remained elusive due to their insolubility. We report the first preparation of unsubstituted para-nonaphenylenes (9PPs) by extending our precursor rout...
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| Hauptverfasser: | , , , , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
January 4, 2021
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| In: |
Chemistry - a European journal
Year: 2021, Jahrgang: 27, Heft: 1, Pages: 281-288 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.202001531 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202001531 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202001531 
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| Verfasserangaben: | Ali Abdulkarim, Marvin Nathusius, Rainer Bäuerle, Karl-Philipp Strunk, Sebastian Beck, Hans Joachim Räder, Annemarie Pucci, Christian Melzer, Daniel Jänsch, Jan Freudenberg, Uwe H.F. Bunz, and Klaus Müllen |
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| 520 | |a The synthesis of unsubstituted oligo-para-phenylenes (OPP) exceeding para-hexaphenylene—in the literature often referred to as p-sexiphenyl—has long remained elusive due to their insolubility. We report the first preparation of unsubstituted para-nonaphenylenes (9PPs) by extending our precursor route to poly-para-phenylenes (PPP) to a discrete oligomer. Two geometric isomers of methoxylated syn- and anti-cyclohexadienylenes were synthesized, from which 9PP was obtained via thermal aromatization in thin films. 9PP was characterized via optical, infrared and solid-state 13C NMR spectroscopy as well as atomic force microscopy and mass spectrometry, and compared to polymeric analogues. Due to the lack of substitution, para-nonaphenylene, irrespective of the precursor isomer employed, displays pronounced aggregation in the solid state. Intermolecular excitonic coupling leads to formation of H-type aggregates, red-shifting emission of the films to greenish. 9PP allows to study the structure-property relationship of para-phenylene oligomers and polymers, especially since the optical properties of PPP depend on the molecular shape of the precursor. | ||
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