Nanometre-sized Macrocyclic Oligoamides by Iterative Synthesis |
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Authors: | Holger Schwierz Fritz Vögtle |
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Institution: | (1) Kekulé-Institut für Organische Chemie und Biochemie der Rheinischen Friedrich, Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany |
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Abstract: | New nanometre-sized macrocyclictosylaza3n]paracyclophanes have been synthesized bymeans of an iterative synthetic strategy using linearbuilding blocks with up to four benzene units. Theformation of the open-chain difunctionalized linearmolecules was achieved by a three step reactionsequence including nucleophilic substitution andtransformation of the terminal ester groups to thecorresponding dialcohol and dibromide. The finalintermolecular macrocyclizations were carried out byreaction of open chained dibromides andbis(tosylamides) to obtain nanosize macrocyclicoligotosylamides in 31–50% yield. Highly symmetricaltosylaza3n]paracyclophanes containing up to sevenbenzene units and up to 49 ring members (n = 5–7) wereobtained. Also described is the preparation of30–90-membered paracyclophanes containing biphenyl orterphenyl units. |
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Keywords: | large rings nanocycles paracyclophanes macrocycles sulfonamides |
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