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Issue 28, 2017
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Stacked homodimers of substituted contorted hexabenzocoronenes and their complexes with C60 fullerene

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Abstract

Stacking interactions involving substituted contorted hexabenzocoronene (c-HBC) with C60 were studied at the B97-D3M(BJ)/TZVPP//B97-D/TZV(2d,2p) level of theory. First, we showed that substituent effects in benzene⋯C60 complexes are uncorrelated with those in the benzene sandwich dimer, underscoring the importance of local, direct interactions in substituent effects in stacking interactions. Second, we showed that c-HBC preferentially forms stacked homodimers over complexes with C60; however, if the bowl depth of c-HBC is increased beyond 1.25 Å, the c-HBC⋯C60 complex becomes preferred over the c-HBC homodimer. Ultimately, we showed that the perfluorination of c-HBC leads to sufficient curvature to allow the c-HBC⋯C60 heterodimers to form preferentially over c-HBC homodimers, suggesting the possibility of the development of c-HBC derivatives that assemble into alternating stacks with C60.

Graphical abstract: Stacked homodimers of substituted contorted hexabenzocoronenes and their complexes with C60 fullerene

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Publication details

The article was received on 31 May 2017, accepted on 21 Jun 2017 and first published on 21 Jun 2017


Article type: Paper
DOI: 10.1039/C7OB01333G
Citation: Org. Biomol. Chem., 2017,15, 6042-6049
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    Stacked homodimers of substituted contorted hexabenzocoronenes and their complexes with C60 fullerene

    D. Sepúlveda, Y. Guan, U. Rangel and S. E. Wheeler, Org. Biomol. Chem., 2017, 15, 6042
    DOI: 10.1039/C7OB01333G

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