Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 9, Pages 2982-2989Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203597
Keywords
crown complexes; lasso; molecular switch; self-entanglement; rotaxanes
Categories
Funding
- Ligue Nationale Contre le Cancer
Ask authors/readers for more resources
The synthesis of a pH-sensitive two-station [1]rotaxane molecular switch by self-entanglement of a non-interlocked hermaphrodite molecule, containing an anilinium and triazole moieties, is reported. The anilinium was chosen as the best template for the macrocycle benzometaphenylene[25]crown-8 (BMP25C8) and allowed the self-entanglement of the molecule. The equilibrium between the hermaphrodite molecule and the pseudo[1]rotaxane was studied by 1HNMR spectroscopy: the best conditions of self-entanglement were found in the less polar solvent CD2Cl2 and at high dilution. The triazole moiety was then benzylated to afford a benzyltriazolium moiety, which then played a dual role. On one hand, it acts as a bulky gate to trap the BMP25C8, thus to avoid any self-disentanglement of the molecular architecture. On another hand, it acts as a second molecular station for the macrocycle. At acidic pH, the BMP25C8 resides around the best anilinium molecular station, displaying the lasso [1]rotaxane in a loosened conformation. The deprotonation of the anilinium molecular station triggers the shuttling of the BMP25C8 around the triazolium moiety, therefore tightening the lasso.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available