Non-Ionic Template Synthesis of Amide-Linked Rotaxanes: Olefinic and Aliphatic Axle Building Blocks

✍ Scribed by Jäger, Ralf ;Baumann, Sven ;Fischer, Marco ;Safarowsky, Oliver ;Nieger, Martin ;Vögtle, Fritz

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 445 KB
• Volume: 1997
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199719971114

✦ Synopsis

constant I Mechanical bonding I Molecular recognition I Template synthesis / Supramolecular chemistry

The first synthesis of amide-linked rotaxanes with non-arene axle building blocks is reported. The threading synthesis of rotaxane 8 with olefinic fumaryl chloride proves that arene moieties are not necessary for non-ionic template syntheses. Mass spectroscopic evidence of a rotaxane bearing an aliphatic axle, derived from succinic acid, revealed that hydrogen bonding, rather than TI,R interactions, is the predominant template binding force. 'H-NMR titration studies on the thre-ading synthesis of these mechanically bonded molecules were carried out. The association constants measured suggest that the incorporation of the corresponding monoamide monochloride (cf. ?), rather than the incorporation of the diacid dichloride (cf. 5), plays the key role in these rotaxane syntheses. The X-ray structural analysis of a semi axle (14) reveals hydrogen bonding patterns characteristic of diamides.