Synthesis and monolayer behavior of amphiphilic per(2,3-di-O-alkyl)-α- and β-cyclodextrins and hexakis(6-deoxy-6-thio-2,3-di-O-pentyl)-α-cyclodextrin at an air–water interface

✍ Scribed by Monika Wazynska; Andrzej Temeriusz; Kazimierz Chmurski; Renata Bilewicz; Janusz Jurczak

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 102 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01628-2

✦ Synopsis

A synthesis of amphiphilic per(2,3-di-O-alkyl)-a-and b-cyclodextrins and hexakis(6-deoxy-6-thio-2,3di-O-pentyl)-a-cyclodextrin and their monolayer behavior on a water surface is presented. Long alkyl chains were introduced by a treatment of the per(6-O-tert-butyldimethylsilyl) derivatives with an appropriate alkyl iodide in dimethylformamide in the presence of sodium hydride. A standard desilylation procedure followed by an iodination reaction afforded per(6-deoxy-6-iodo) analogues. In the latter reaction step, sulphur containing groups were introduced by nucleophilic substitution of the iodine with benzothiolate ion in dimethylformamide. The hexakis(6-deoxy-6-S-benzyl-2,3-di-O-pentyl)-a-cyclodextrin was transformed into extremely interesting hexakis(6-deoxy-6-thio-2,3-di-O-pentyl)-a-cyclodextrin. The surface pressure-mean molecular area (y-A) isotherms indicated that the synthesised amphiphilic cyclodextrin derivatives were capable of forming stable monolayers at the air-water interface. The shapes of the isotherms were typical for solid-like monolayers except for hexakis(6-deoxy-6-thio-2,3-di-O-pentyl)cyclomaltohexaoses which formed a more liquid monolayer.