Peralkylated coronenes via regiospecific hydrogenation of hexa-peri-hexabenzocoronenes

M.D. Watson, M.G. Debije, J.M. Warman, K. Müllen

Research output: Contribution to journalArticleAcademicpeer-review

24 Citations (Scopus)

Abstract

A remarkable, regiospecific hydrogenation zips around the 4 nm perimeter of hexa-peri-hexabenzocoronenes (HBC) adding 18 hydrogen atoms, leading to the first peralkylated coronenes, in quantitative yields in some cases. Increasing steric bulk of side chains was found to hinder the reaction, while unsubstituted HBC could be converted to a modest extent despite its vanishing solubility. The structures of the novel coronenes are unequivocally confirmed by MALDI-TOF, 1H, 13C, and heteronuclear correlation NMR, and UV-vis absorption spectroscopy. The puckered-ring periphery of these discotics does not prohibit self-assembly to columnar structures in a fashion similar to that of the planar precursors, as determined from wide-angle X-ray diffraction, but decreases the isotropization temperature by 300 °C relative to the latter. Branching in the alkyl chains frustrates nucleation from the melt, resulting in clear polymorphism depending on the thermal treatment. Nonetheless, preliminary measurements indicate high charge-carrier mobilities and lifetimes within the bulk material, on the same order as those previously found for HBCs.
LanguageEnglish
Pages766-771
JournalJournal of the American Chemical Society
Volume126
Issue number3
DOIs
StatePublished - 2004

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Biomolecular Nuclear Magnetic Resonance
Hydrogenation
Carrier lifetime
Carrier mobility
Matrix-Assisted Laser Desorption-Ionization Mass Spectrometry
Ultraviolet spectroscopy
Polymorphism
Charge carriers
Absorption spectroscopy
X-Ray Diffraction
Solubility
Self assembly
Hydrogen
Spectrum Analysis
Nucleation
Hot Temperature
Heat treatment
Nuclear magnetic resonance
X ray diffraction
Atoms

Cite this

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title = "Peralkylated coronenes via regiospecific hydrogenation of hexa-peri-hexabenzocoronenes",
abstract = "A remarkable, regiospecific hydrogenation zips around the 4 nm perimeter of hexa-peri-hexabenzocoronenes (HBC) adding 18 hydrogen atoms, leading to the first peralkylated coronenes, in quantitative yields in some cases. Increasing steric bulk of side chains was found to hinder the reaction, while unsubstituted HBC could be converted to a modest extent despite its vanishing solubility. The structures of the novel coronenes are unequivocally confirmed by MALDI-TOF, 1H, 13C, and heteronuclear correlation NMR, and UV-vis absorption spectroscopy. The puckered-ring periphery of these discotics does not prohibit self-assembly to columnar structures in a fashion similar to that of the planar precursors, as determined from wide-angle X-ray diffraction, but decreases the isotropization temperature by 300 °C relative to the latter. Branching in the alkyl chains frustrates nucleation from the melt, resulting in clear polymorphism depending on the thermal treatment. Nonetheless, preliminary measurements indicate high charge-carrier mobilities and lifetimes within the bulk material, on the same order as those previously found for HBCs.",
author = "M.D. Watson and M.G. Debije and J.M. Warman and K. M{\"u}llen",
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journal = "Journal of the American Chemical Society",
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Peralkylated coronenes via regiospecific hydrogenation of hexa-peri-hexabenzocoronenes. / Watson, M.D.; Debije, M.G.; Warman, J.M.; Müllen, K.

In: Journal of the American Chemical Society, Vol. 126, No. 3, 2004, p. 766-771.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - Peralkylated coronenes via regiospecific hydrogenation of hexa-peri-hexabenzocoronenes

AU - Watson,M.D.

AU - Debije,M.G.

AU - Warman,J.M.

AU - Müllen,K.

PY - 2004

Y1 - 2004

N2 - A remarkable, regiospecific hydrogenation zips around the 4 nm perimeter of hexa-peri-hexabenzocoronenes (HBC) adding 18 hydrogen atoms, leading to the first peralkylated coronenes, in quantitative yields in some cases. Increasing steric bulk of side chains was found to hinder the reaction, while unsubstituted HBC could be converted to a modest extent despite its vanishing solubility. The structures of the novel coronenes are unequivocally confirmed by MALDI-TOF, 1H, 13C, and heteronuclear correlation NMR, and UV-vis absorption spectroscopy. The puckered-ring periphery of these discotics does not prohibit self-assembly to columnar structures in a fashion similar to that of the planar precursors, as determined from wide-angle X-ray diffraction, but decreases the isotropization temperature by 300 °C relative to the latter. Branching in the alkyl chains frustrates nucleation from the melt, resulting in clear polymorphism depending on the thermal treatment. Nonetheless, preliminary measurements indicate high charge-carrier mobilities and lifetimes within the bulk material, on the same order as those previously found for HBCs.

AB - A remarkable, regiospecific hydrogenation zips around the 4 nm perimeter of hexa-peri-hexabenzocoronenes (HBC) adding 18 hydrogen atoms, leading to the first peralkylated coronenes, in quantitative yields in some cases. Increasing steric bulk of side chains was found to hinder the reaction, while unsubstituted HBC could be converted to a modest extent despite its vanishing solubility. The structures of the novel coronenes are unequivocally confirmed by MALDI-TOF, 1H, 13C, and heteronuclear correlation NMR, and UV-vis absorption spectroscopy. The puckered-ring periphery of these discotics does not prohibit self-assembly to columnar structures in a fashion similar to that of the planar precursors, as determined from wide-angle X-ray diffraction, but decreases the isotropization temperature by 300 °C relative to the latter. Branching in the alkyl chains frustrates nucleation from the melt, resulting in clear polymorphism depending on the thermal treatment. Nonetheless, preliminary measurements indicate high charge-carrier mobilities and lifetimes within the bulk material, on the same order as those previously found for HBCs.

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