Beyond p-hexaphenylenes: synthesis of unsubstituted p-nonaphenylene by a precursor protocol

Medientyp: E-Artikel

Titel: Beyond p-hexaphenylenes : synthesis of unsubstituted p-nonaphenylene by a precursor protocol

Beteiligte: Abdulkarim, Ali [Verfasser:in]; Nathusius, Marvin [Verfasser:in]; Bäuerle, Rainer [Verfasser:in]; Strunk, Karl-Philipp [Verfasser:in]; Beck, Sebastian [Verfasser:in]; Räder, Hans Joachim [Verfasser:in]; Pucci, Annemarie [Verfasser:in]; Melzer, Christian [Verfasser:in]; Jänsch, Daniel [Verfasser:in]; Freudenberg, Jan [Verfasser:in]; Bunz, Uwe H. F. [Verfasser:in]; Müllen, Klaus [Verfasser:in]

Erschienen: January 4, 2021

Sprache: Englisch

DOI: 10.1002/chem.202001531

Identifikator:

Schlagwörter: conjugation ; oligo-para-phenylene ; pi interaction ; precursor route

Entstehung:

Anmerkungen: Online veröffentlicht: 12 August 2020

Beschreibung: 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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