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A Shape-Persistent Polyphenylene Spoked Wheel

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Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany
Division of Molecular Imaging and Photonics, Department of Chemistry, KU Leuven-University of Leuven, Celestijnenlaan 200 F, 3001 Leuven, Belgium
§ Center for Advancing Electronics Dresden (cfaed) and Department of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01062 Dresden, Germany
Cite this: J. Am. Chem. Soc. 2016, 138, 48, 15539–15542
Publication Date (Web):November 16, 2016
https://doi.org/10.1021/jacs.6b10369
Copyright © 2016 American Chemical Society

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    Abstract

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    A shape-persistent polyphenylene with a “spoked wheel” structure was synthesized as a subunit of an unprecedented two-dimensional polyphenylene that we name graphenylene. The synthesis was carried out through a sixfold intramolecular Yamamoto coupling of a dodecabromo-substituted dendritic polyphenylene precursor, which had a central hexaphenylbenzene unit as a template. Characterizations by NMR spectroscopy and matrix-assisted laser ionization time-of-flight mass spectrometry provided an unambiguous structural proof for the wheel-like molecule with a molar mass of 3815.4 g/mol. Remarkably, scanning tunneling microscopy visualization clearly revealed the defined spoked wheel structure of the molecule with six internal pores.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.6b10369.

    • Experimental details; cyclic voltammograms; NMR, UV–vis absorption, fluorescence, and MALDI-TOF MS spectra; and additional STM images and molecular models (PDF)

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