Synthesis of a Giant 222 Carbon Graphite Sheet

In this paper we present the synthesis and characterization of the so far largest polycyclic aromatic hydrocarbon (PAH), containing 222 carbon atoms or 37 separate benzene units. First a suitable three‐dimensional oligophenylene precursor molecule is built up by a sequence of Diels–Alder and cyclotr...

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Bibliographic Details
Published in:Chemistry : a European journal 2002-03, Vol.8 (6), p.1424-1429
Main Authors: Simpson, Christopher D., Brand, J. Diedrich, Berresheim, Alexander J., Przybilla, Laurence, Räder, Hans Joachim, Müllen, Klaus
Format: Article
Language:English
Subjects:
carbon
cyclodehydrogenation
graphite
mass spectrometry
polycycles
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Summary:In this paper we present the synthesis and characterization of the so far largest polycyclic aromatic hydrocarbon (PAH), containing 222 carbon atoms or 37 separate benzene units. First a suitable three‐dimensional oligophenylene precursor molecule is built up by a sequence of Diels–Alder and cyclotrimerization reactions and then planarized in the final step by oxidative cyclodehydrogenation to the corresponding hexagonal PAH. Structural proof is based on isotopically resolved MALDI‐TOF mass spectra and electronic characteristics are studied by UV/Vis spectroscopy. By using highly efficient oxidative cyclodehydrogenation conditions, a soluble oligophenylene precursor molecule affords a 222 carbon atom containing giant polycyclic aromatic hydrocarbon 1 through the removal of 108 hydrogens in one step. Analysis is performed by MALDI‐TOF mass spectrometry for which solid‐state sample preparation methods are optimized. Electronic properties of this model compound for graphite are determined by UV/Vis spectroscopy.
ISSN:0947-6539
1521-3765
DOI:10.1002/1521-3765(20020315)8:6<1424::AID-CHEM1424>3.0.CO;2-Z