Variable ion selectivity in [N.3.3](1,3,5)crownophanes: the "breathing" process.
[reaction: see text] A series of dithia[n.3.3](1.3.5)crownophanes were synthesized by cesium carbonate-assisted intramolecular cyclization reactions in 10-31% yields. Their complexation behavior exhibits an unusual ion-selectivity preference due to the presence of a "breathing" process of the dithia[3.3]metacyclophane moiety, which indirectly controls the ion selectivity through the adjustment of the cavity size of the crown unit. This breathing mechanism is also supported by observation made in X-ray crystallographic analysis.
Xu
Jianwei
J
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Lai
Yee-Hing
YH
Wang
Weiling
W