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Shape-Selective Crystallisation of Fluxional Carbon Cages

Bismillah, A.N.; Sturala, J.; Chapin, B.M.; Yufit, D.S.; Hodgkinson, P.; McGonigal, P.R.

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A.N. Bismillah

J. Sturala

B.M. Chapin


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.


Bismillah, A., Sturala, J., Chapin, B., Yufit, D., Hodgkinson, P., & McGonigal, P. (2018). Shape-Selective Crystallisation of Fluxional Carbon Cages. Chemical Science, 9(46), 8631-8636.

Journal Article Type Article
Acceptance Date Oct 19, 2018
Online Publication Date Oct 22, 2018
Publication Date Dec 14, 2018
Deposit Date Jul 30, 2018
Publicly Available Date Nov 29, 2018
Journal Chemical Science
Print ISSN 2041-6520
Electronic ISSN 2041-6539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 9
Issue 46
Pages 8631-8636


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