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• W2080472210 abstract "While Collet’s cryptophanes allow the guest to enter and exit the host cavity, Cram developed the carcerands and hemicarcerends and coined the term “molecular container compounds” for these hosts, which permanently enclose their guests. However, the real explosion in the field of molecular cages and capsules occurred following the introduction of self-assembled molecular capsules by Rebek. Self-assembled molecular cages and capsules are formed spontaneously under thermodynamic control with high precision and efficacy, resembling capsule formation in nature. Self-assembled molecular cages comprising up to 50 building units were prepared. In the last fifteen years, multitudes of self-assembled molecular cages and capsules based on various non-covalent interactions such as metal–ligand bonds, hydrogen bonds, and van der Waals and electrostatic interactions have been prepared and studied in the solid state, in solution, and even in the gas phase. Since the identification of the dimeric capsules of tetraureacalix[4]arenes by Rebek and others, many systems were shown to form hydrogen-bond dimeric capsules. More recently, Böhmer has used these dimeric capsules to synthesize molecules with very intriguing topologies. More than a decade ago resorcin[4]arenes (1) and then pyrogallol[4]arenes (2) were shown to form hexameric capsules in the solid state using 60 and 72 hydrogen bonds, respectively. Rebek then showed, unequivocally, that resorcin[4]arenes form hexameric capsule in solution of organic solvents in the presence of the appropriate guests. Thereafter, Avram and Cohen showed, with the aid of diffusion NMR, that 1 and 2 spontaneously form hexameric capsules of the 16(H2O)8-type and 26 type, respectively, in conventional organic solvents such as chloroform. Dalcanale prepared dimeric capsules based on metal–ligand interactions and Fujita, Raymond, and others have prepared molecular cages composed from many well-organized building blocks with tailored geometries, resulting in cages of different sizes and shapes that were shown also to perform new chemistry. Reinhoudt has shown that electrostatic interactions can be used to prepare such capsules and, more recently, Gibb demonstrated that van der Waals interactions and hydrophobic interactions enable the formation of molecular capsules in aqueous solutions. Much of the interest in molecular containers lies in their synthesis, the study of their structure and dynamic, their guest affinity, and more. However, the most intriguing and important characteristics of such molecules is their use as nano-reactors, in which new chemistry may evolve. Already in the early days Cram, Warmuth, and others demonstrated that carcerands and hemicarcerends can be used to stabilize reactive intermediates. Later self-assembled molecular capsules and cages were shown, by Fujita, Raymond, and others, to catalyze reactions and to affect the course of chemical reactions. Indeed, molecules encapsulated in confined geometries were shown, inter alia, to yield different products than the bulk reactants. Very recently such molecular capsules were shown to affect the photo-physics of different molecules, to affect the redox characteristics of redox-active guests, to change the photochemistry of a series of substrates, and to act as molecular photo-switches. In the current issue tetraureacalixpyrrole dimers are reviewed by Ballester, while Rissanen and coworkers focus on self-assembled dimeric capsules of resorcinarenes in the solid state and Hardie describes cages based on cyclotriveratrylene, The papers of the Atwood and the Mattay groups, two pioneers in the field of hexameric capsules, deal with the hexameric capsules of pyrogallolarenes and resorcinarenes, respectively. Dalcanale describes cavitand-based coordination cages, and Kaifer’s paper deals with the electrochemistry of redox-active encapsulated guests, while the papers of Ramamurthy and Rebek deal with photo-chemistry and photo-physics of encapsulated guests and cages. Gibb’s paper outlines the considerations for self-assembly in aqueous solutions and Warmuth has reviewed the formation of polyimine container molecules, in which up to 24 bonds are formed in a single one-pot reaction. All these papers reflect the intensive activity in recent years in the field of Cages and Molecular Capsules. We wish to take this opportunity to thank all the contributors of this issue for their excellent papers and Elcya Weiss for her very professional and timely assistance in producing this special issue of the Israel Journal of Chemistry.1 1" @default.
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• W2080472210 date "2011-07-01" @default.
• W2080472210 modified "2023-10-16" @default.
• W2080472210 title "Guest Editorial: Cages and Molecular Capsules: From Structure to Catalysis" @default.
• W2080472210 doi "https://doi.org/10.1002/ijch.201100071" @default.
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