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Updated: Jun 16, 2025

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
Dynamic and solid-state behaviour of bromoisotrianglimine.
Abbie M Scholes1, Laurence J Kershaw Cook1, Filip T Szczypiński1
1Department of Chemistry and Materials Innovation Factory, School of Physical Sciences, University of Liverpool UK anna.slater@liverpool.ac.uk.
Researchers explored dynamic imine macrocycles for industrial separations. They controlled structures using crystallization, yielding new macrocycle forms and packing arrangements.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Discrete imine macrocycles are promising for industrial separations.
- Their dynamic behavior during synthesis and crystallization presents challenges.
- Controlling the structure of these dynamic covalent materials is crucial for their application.
Purpose of the Study:
- To investigate the dynamic nature of a C-5 brominated isotrianglimine.
- To explore strategies for structural control in solution and during crystallization.
- To demonstrate methods for forming new isotrianglimine materials by exploiting dynamic behavior.
Main Methods:
- Investigated solution equilibrium between [3 + 3] and [2 + 2] macrocycles.
- Utilized solvent templating during crystallization to influence packing motifs.
- Employed chiral self-sorting to manipulate macrocycle equilibrium and crystal structures.
Main Results:
- Characterized both [3 + 3] and [2 + 2] macrocycles in solution.
- Formed new packing motifs for the [3 + 3] macrocycle and an unreported [4 + 4] macrocycle via solvent templating.
- Demonstrated that crystallization conditions can alter packing and shift macrocycle equilibrium, yielding novel structures.
Conclusions:
- Three strategies were exemplified for controlling isotrianglimine material structures by exploiting dynamic behavior.
- Understanding dynamic behavior is essential for designing and crystallizing functional dynamic covalent materials.
- This work provides a framework for developing advanced materials from dynamic imine macrocycles.
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