Selbstorganisation von Chinodimethanen über kovalente Bindungen, Mitteilung III , Untersuchungen zur Herstellung von Nanostrukturen

✍ Scribed by Junes Ipaktschi; Rahman Hosseinzadeh; Peter Schlaf; Thomas Eckert

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: German
• Weight: 306 KB
• Volume: 83
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/1522-2675(20000607)83:6<1224::aid-hlca1224>3.0.co;2-n

✦ Synopsis

Self-Assembly of Quinodimethanes through Covalent Bonds. Part III. Investigations on the Preparation of Nanostructures As part of our studies on the tetramerization of quinodimethane 1 to the macrocyclic compound 2, the influence of substituents on this reaction was investigated. It was found that a large range of substituents such as 2-phenylethyl, 2-(4-methoxyphenyl)ethyl, 2-(4-fluorophenyl)ethyl, 2-[4-(tert-butyl)phenyl]ethyl, and 2-[4-(2phenylethyl)phenyl]ethyl, attached at positions 2 and 7 of 9H-fluorene, do not prevent the tetramerization.

The key step in the formation of the macrocylic compounds 13a ± e is the debromination of 12a ± e with mercury to the corresponding quinodimethanes which undergo a self-assembly forming 13a ± e in high yields. To study the conjugative influence of substituents on tetramerization, the effect of the hex-1-ynyl groups at positions 3 and 6 of the 9H-fluorene rings was investigated. In this case, the corresponding macrocycle 17 was generated by the reaction of diol 16a with SnCl 2 . Although the expected tetramerization to 17 occurred, the yield was lower than in the case of 13a ± e, due to the sensitivity of the product.