Organic Imine Cages: Molecular Marriage and Applications

Abstract

Imine condensation has been known to chemists for more than a century and is used extensively to synthesize large organic cages of defined shapes and sizes. Surprisingly, in the context of the synthetic methods for organic imine cages (OICs), a self‐sorting/self‐selection (molecular marriage) process has been overlooked over the years. Such processes are omnipresent in nature, from the creation of galaxies to the formation of the smallest building blocks of life (the cell). Such processes have the incredible ability to guide a system toward the formation of a specific product or products out of a collection of equally probable multiple possibilities. This Minireview sheds light on new opportunities in cage design offered by the self‐sorting/self‐selection protocol in OICs. Recent efforts to explore organic cages for various exciting new applications are discussed; for example, for detection of harmful small organic molecules, as templates for nucleation of metal nanoparticles (MNPs), and as proton‐conducting materials.

Porous Organic Cages

“…The recent surge in their development has benefited from breakthroughs in advanced analytical techniques, particularly in gas-adsorption and X-ray diffraction techniques. In this regard, there are already a few published reviews. ,,,,,,,− Some of these reviews have focused on special types of POCs, such as multiporphyrinic or imine , cages, while others have summarized the advent of new porous organic materials, ,, involving POCs only in part. Others have covered one special aspectfor example, unique synthetic approaches, − , narrow functionalization angles, or small applications scope .…”

Electron-Deficient Au Nanoparticles Confined in Organic Molecular Cages for Catalytic Reduction of 4-Nitrophenol

“…Since the discovery of organic molecular cages, the scientific community’s research interest in these porous materials has steadily grown. − Compared with most three-dimensional porous open frames, the vast majority of porous organic cages (POCs) possess very unique properties, which means they can be well dissolved in common organic solvents, with good stability and dispersibility. On the other hand, their excellent solubilities enable them to be well composited with various materials, which broadens their applications (e.g., small molecule separation, − sensing, , molecular components of polymers, , and nanoparticle templates − ).…”

Anisotropic Compartmentalization of the Liquid–Liquid Interface using Dynamic Imine Chemistry

“…It is a reversible reaction that operates under thermodynamic control. For this fundamental reason, the dynamic imine bond has been successfully used for constructing molecular cages, 19 emulsions, 20,21 synthetic protocells, 22 stimuli-responsive polymers, 23 COFs, 24,25 motor, 26 micelles, 27 vesicles, 28,29 and functional coatings. 30,31 Despite the enormous utilization of imine bond chemistry for the fabrication and modulation of functional assemblies, there has been limited focus on its application for liquid−liquid interfacial assemblies.…”

“…It is a reversible reaction that operates under thermodynamic control. For this fundamental reason, the dynamic imine bond has been successfully used for constructing molecular cages, emulsions, , synthetic protocells, stimuli-responsive polymers, functional COFs, , motor, micelles, vesicles, , and functional coatings. , …”