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Issue 12, 2015
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π-extended [12]cycloparaphenylenes: from a hexaphenylbenzene cyclohexamer to its unexpected C2-symmetric congener

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Abstract

The synthesis of π-extended [12]cycloparaphenylene (CPP) derivatives from a kinked triangular macrocycle is presented. Depending on the reaction conditions for reductive aromatization, either a hexaphenylbenzene cyclohexamer or its C2-symmetric congener was obtained. Their structures were confirmed by NMR spectroscopy or X-ray crystallographic analysis. With the support of DFT calculations, a mechanistic explanation for the unexpected formation of the oval shaped bis(cyclohexadiene)-bridged C2-symmetric macrocycle is provided. The here employed congested hexaphenylbenzene mode of connectivity in conjunction with a non-strained precursor improves oxidative cyclodehydrogenation toward the formation of ultrashort carbon nanotubes (CNT)s. Thus, this strategy can pave the way for new conceptual approaches of a solution-based bottom-up synthesis of CNTs.

Graphical abstract: π-extended [12]cycloparaphenylenes: from a hexaphenylbenzene cyclohexamer to its unexpected C2-symmetric congener

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Publication details

The article was received on 14 Jul 2015, accepted on 08 Sep 2015 and first published on 08 Sep 2015


Article type: Edge Article
DOI: 10.1039/C5SC02547H
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Citation: Chem. Sci., 2015,6, 7072-7078
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    π-extended [12]cycloparaphenylenes: from a hexaphenylbenzene cyclohexamer to its unexpected C2-symmetric congener

    F. E. Golling, S. Osella, M. Quernheim, M. Wagner, D. Beljonne and K. Müllen, Chem. Sci., 2015, 6, 7072
    DOI: 10.1039/C5SC02547H

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