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Issue 46, 2018
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Shape-selective crystallisation of fluxional carbon cages

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Abstract

Dynamic covalent rearrangements of fluxional carbon cages, such as bullvalenes and barbaralanes, impart ‘shapeshifting’ molecular properties. Here, a series of five barbaralanes each interconvert dynamically between two constitutional isomers in solution, but resolve to single isomers upon crystallisation. Unexpectedly, the minor solution-phase isomers are resolved in two instances. Through dynamic NMR, crystallographic and DFT analyses, we show that the isomer observed in the solid state is not a direct consequence of the equilibrium distribution in solution or any specific noncovalent interactions. Rather, the dynamic preferential crystallisation is dictated by differences in molecular size and shape.

Graphical abstract: Shape-selective crystallisation of fluxional carbon cages

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Publication details

The article was received on 27 Sep 2018, accepted on 19 Oct 2018 and first published on 22 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC04303E
Chem. Sci., 2018,9, 8631-8636
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Shape-selective crystallisation of fluxional carbon cages

    A. N. Bismillah, J. Sturala, B. M. Chapin, D. S. Yufit, P. Hodgkinson and P. R. McGonigal, Chem. Sci., 2018, 9, 8631
    DOI: 10.1039/C8SC04303E

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