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Selbstorganisation von Chinodimethanen über kovalente Bindungen, Mitteilung III , Untersuchungen zur Herstellung von Nanostrukturen
Author(s) -
Ipaktschi Junes,
Hosseinzadeh Rahman,
Schlaf Peter,
Eckert Thomas
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000607)83:6<1224::aid-hlca1224>3.0.co;2-n
Subject(s) - chemistry , fluorene , yield (engineering) , covalent bond , stereochemistry , diol , medicinal chemistry , polymer , organic chemistry , materials science , metallurgy
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‐(2‐phenylethyl)phenyl]ethyl, attached at positions 2 and 7 of 9 H ‐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 9 H ‐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.