Issue 36, 2024

Correlated shapeshifting and configurational isomerization

Abstract

Herein we demonstrate that the rapid ‘shapeshifting’ constitutional isomerization of a substituted bullvalene is influenced by the E-to-Z configurational isomerization of a remote carbamate group, giving rise to correlated motion. We find that, while the E-configurational isomer of a bulky carbamate favors the β-bullvalene constitutional isomer, a noncovalent bonding interaction within the Z-carbamate tips the equilibrium toward the γ-bullvalene form. Using DFT modelling and NMR spectroscopy, this long-range interaction is identified as being between the bullvalene core and a pendant phenyl group connected to the carbamate. Coupling the constitutional changes of a bullvalene to a reciprocal configurational isomerization through a long-range interaction in this way will allow shapeshifting rearrangements to be exploited as part of collective motion in extended structures.

Graphical abstract: Correlated shapeshifting and configurational isomerization

Supplementary files

Article information

Article type
Edge Article
Submitted
06 iyn 2024
Accepted
23 avq 2024
First published
23 avq 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 14618-14624

Correlated shapeshifting and configurational isomerization

B. A. Hussein, W. Maturi, M. K. Rylands, A. N. Bismillah, Y. Wen, J. A. Aguilar, R. Ayub, C. D. Rankine and P. R. McGonigal, Chem. Sci., 2024, 15, 14618 DOI: 10.1039/D4SC03699A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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