Dynamic and solid-state behaviour of bromoisotrianglimine

12 December 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Solid-state materials formed from discrete imine macrocycles have potential in industrial separations, but dynamic behaviour during both synthesis and crystallisation makes them challenging to exploit. Here, we explore opportunities for structural control by investigating the dynamic nature of a C-5 brominated isotrianglimine in solution and under crystallisation conditions. In solution, the equilibrium between the [3+3] and the less reported [2+2] macrocycle was investigated, and both macrocycles were fully characterised. Solvent templating during crystallisation was used to form new packing motifs for the [3+3] macrocycle and an unreported [4+4] macrocycle. Finally, chiral self-sorting was used to demonstrate how crystallisation conditions can not only influence packing arrangements but also shift the macrocycle equilibrium to yield new structures. This work thus exemplifies three strategies for exploiting dynamic behaviour to form isotrianglimine materials, and highlights the importance of understanding the dynamic behaviour of a system when designing and crystallising functional materials formed using dynamic covalent chemistry.


organic materials
crystal engineering

Supplementary materials

Dynamic Behaviour and Crystallisation of Bromoisotrianglimine - Supporting information
Including experimental details, synthesis, diffusion NMR decay curves, single crystal XRD details, molecular modelling.


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