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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]

Beyond p-hexaphenylenes

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  • Media type: E-Article
  • Title: Beyond p-hexaphenylenes : synthesis of unsubstituted p-nonaphenylene by a precursor protocol
  • Contributor: 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]
  • Published: January 4, 2021
  • Published in: Chemistry - a European journal ; 27(2021), 1, Seite 281-288
  • Language: English
  • DOI: 10.1002/chem.202001531
  • Identifier:
  • Keywords: conjugation ; oligo-para-phenylene ; pi interaction ; precursor route
  • Origination:
  • Footnote: Online veröffentlicht: 12 August 2020
  • Description: 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.
  • Access State: Open Access