From branched hydrocarbon propellers to C3-symmetric graphite disks

Jishan Wu, Željko Tomović, Volker Enkelmann, Klaus Müllen

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89 Citations (Scopus)


Branched hydrocarbon propellers (9 and 12) were prepared by stepwise palladium-catalyzed Hagihara-Sonogashira coupling reactions and Diels-Alder cycloadditions and submitted to oxidative cyclodehydrogenation by FeCl 3 to afford two new giant graphite disks 2 and 3 with 3-fold symmetry in high yield. One of the precursors, the polyphenylene dendrimer 9 containing 150 carbon atoms, was crystallographically characterized. The poorly soluble graphite disks were characterized by isotope-resolved MALDI-TOF mass spectroscopy, and their electronic and vibrational properties were investigated by solid-state UV-vis and Raman spectroscopy. The effect of molecular size and geometry on their properties was discussed. The molecule 2 represents the largest, 3-fold-symmetric all-benzenoid graphite disk, and the five-membered rings in molecule 3 open the opportunity to synthesize large bowl-shaped PAHs.

Original languageEnglish
Pages (from-to)5179-5186
Number of pages8
JournalJournal of Organic Chemistry
Issue number16
Publication statusPublished - 6 Aug 2004
Externally publishedYes


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