1999
DOI: 10.1055/s-1999-3385
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Linear and Macrocyclic Molecular Thread, Ribbon and Belt Assemblies of Nanometric Scale

Abstract: The hitherto longest molecular thread-belt assemblies 8 , 29 , 32 and 43 based on benzene-connected [3.3]metacyclophane units were prepared by means of a repetitive synthetic method. The preparation of difunctionalized [3.3]metacyclophane units (14 , 22 , 26) succeeded in good yields by an iteration sequence including the cyclization to the cyclophane skeleton and the derivatization of the ester groups. The covalent linkage of the [3.3]metacyclophane belt parts to the thread part leads to higher product yields… Show more

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Cited by 14 publications
(9 citation statements)
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“…Investigations into the construction of larger cyclophanes proceeded through the generation of linear oligomers of tetrasubstituted aryl moieties linked through tosylated aminomethyl groups. Through iterative synthesis, chain lengths up to the nonamer 401 were obtained and crystal structures for pentamer 21 revealed stacked, molecular ribbons (Figure ).…”
Section: Cyclophanesmentioning
confidence: 99%
“…Investigations into the construction of larger cyclophanes proceeded through the generation of linear oligomers of tetrasubstituted aryl moieties linked through tosylated aminomethyl groups. Through iterative synthesis, chain lengths up to the nonamer 401 were obtained and crystal structures for pentamer 21 revealed stacked, molecular ribbons (Figure ).…”
Section: Cyclophanesmentioning
confidence: 99%
“…As discussed above, pathway a is preferred to pathway b. Formation of 5 by treatment of 2 with the dibromide 8 requires 0.5 equivalents of 8 and some sort of protection or blocking in the sulfonamide [11] to avoid the reaction leading to 4. Conversion of 5 into 3 would require an excess of 8 in order to preserve both bromine atoms in 3.…”
Section: Resultsmentioning
confidence: 99%
“…Conversion of 5 into 3 would require an excess of 8 in order to preserve both bromine atoms in 3 . Formation of 5 by treatment of 2 with the dibromide 8 requires 0.5 equivalents of 8 and some sort of protection or blocking in the sulfonamide11 to avoid the reaction leading to 4 .…”
Section: Resultsmentioning
confidence: 99%