Functionalized Calixarenes: New Applications as Catalysts, Ligands, and Host Molecules

  • Seiji Shinkai
Chapter
Part of the Topics in Inclusion Science book series (TISC, volume 3)

Abstract

Calixarenes are cavity-shaped cyclic molecules made up of phenol units linked via alkylidene groups (meta-cyclophanes). In spite of their attractive architecture, studies of host—guest chemistry related to calixarenes have been very limited [1–3]. In fact, Gutsche stated in his 1985 review article that there are no published data in support of solution complexes of calixarenes [2]. This is in sharp contrast to cyclodextrins which can form a variety of host—guest-type solution complexes. We considered that this difference is related to solubility: the host—guest chemistry of cyclodextrins has been studied in aqueous systems where the hydrophobic force is broadly operative for the stabilization of the host—guest complexes, whereas the efforts to seek evidence for solution complexes of calixarenes have been made in organic solvents where the host molecule must compete with solvent molecules for the guest [1–3]. We thus concluded that in order to find evidence for solution complexes, the primary experimental effort should be directed towards solubilization of calixarenes in water: this was the starting point of our calixarene studies [4, 5]. We have synthesized anionic, cationic, and neutral water-soluble calixarenes and obtained unequivocal evidence for the formation of solution complexes in aqueous systems [4, 5]. In this article we review the past development of functionalized calixarenes and discuss how calixarenes can be used as catalysts, ligands, and host molecules and the essential characteristics of calixarenes in comparison to cyclodextrins and crown ethers.

Keywords

Critical Micelle Concentration Crown Ether Guest Molecule Host Molecule Cone Conformation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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© Kluwer Academic Publishers 1991

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  • Seiji Shinkai

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