Dynamic and solid-state behaviour of bromoisotrianglimine.

Autor: Scholes AM; Department of Chemistry and Materials Innovation Factory, School of Physical Sciences, University of Liverpool UK anna.slater@liverpool.ac.uk., Kershaw Cook LJ; Department of Chemistry and Materials Innovation Factory, School of Physical Sciences, University of Liverpool UK anna.slater@liverpool.ac.uk., Szczypiński FT; Department of Chemistry and Materials Innovation Factory, School of Physical Sciences, University of Liverpool UK anna.slater@liverpool.ac.uk., Luzyanin KV; Department of Chemistry and Materials Innovation Factory, School of Physical Sciences, University of Liverpool UK anna.slater@liverpool.ac.uk., Egleston BD; Department of Chemistry, Molecular Sciences Research Hub Imperial College London London UK., Greenaway RL; Department of Chemistry, Molecular Sciences Research Hub Imperial College London London UK., Slater AG; Department of Chemistry and Materials Innovation Factory, School of Physical Sciences, University of Liverpool UK anna.slater@liverpool.ac.uk.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2024 Aug 13. Date of Electronic Publication: 2024 Aug 13.
DOI: 10.1039/d4sc04207g
Abstrakt: 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 a previously 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.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE