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Preparation of Pillar[5]arene‐Based [2]Rotaxanes by a Stopper‐Exchange Strategy
Author(s) -
Nierengarten Iwona,
Meichsner Eric,
Holler Michel,
Pieper Pauline,
Deschenaux Robert,
DelavauxNicot Béatrice,
Nierengarten JeanFrançois
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703997
Subject(s) - rotaxane , pillar , chemistry , axle , molecular machine , chloride , combinatorial chemistry , polymer chemistry , supramolecular chemistry , organic chemistry , molecule , materials science , nanotechnology , mechanical engineering , structural engineering , engineering
A pillar[5]arene‐containing rotaxane building block bearing exchangeable stoppers has been prepared in multigram scale quantities with high yields from the reaction of 2,4‐dinitrophenol (DNP) with the inclusion complex resulting from the association of dodecanedioyl chloride with 1,4‐diethoxypillar[5]arene. Stopper exchange reactions have been achieved by treatment of the resulting DNP diester with various amines through an addition–elimination mechanism preventing the unthreading of the axle component during the reaction and thus preserving the [2]rotaxane structures. The resulting diamide [2]rotaxane derivatives have thus been obtained in good to excellent yields. Importantly, [2]rotaxanes difficult or impossible to prepare by direct introduction of the two stoppers in a single synthetic step are now easily available.