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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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Main Authors: Abdulkarim, Ali (Author) , Nathusius, Marvin (Author) , Bäuerle, Rainer (Author) , Strunk, Karl-Philipp (Author) , Beck, Sebastian (Author) , Räder, Hans Joachim (Author) , Pucci, Annemarie (Author) , Melzer, Christian (Author) , Jänsch, Daniel (Author) , Freudenberg, Jan (Author) , Bunz, Uwe H. F. (Author) , Müllen, Klaus (Author)
Format: Article (Journal)
Language:English
Published: January 4, 2021
In: Chemistry - a European journal
Year: 2021, Volume: 27, Issue: 1, Pages: 281-288
ISSN:1521-3765
DOI:10.1002/chem.202001531
Online Access: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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Author Notes: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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Summary: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.
Item Description:Online veröffentlicht: 12 August 2020
Gesehen am 28.02.2024
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202001531

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