Abstract
| Original language | Undefined |
|---|---|
| Pages (from-to) | 436-445 |
| Journal | Chemistry: a European journal |
| Volume | 2 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 1996 |
Keywords
- METIS-105886
- IR-10885
Cite this
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1,3-Alternate calix[4]arenecrown-5 conformers: new synthetic ionophores with better K+/Na+ selectivity than valinomycin. / Casnati, Alessandro; Pochini, Andrea; Ungaro, Rocco; Bocchi, Carlo; Ugozzoli, Franco; Egberink, Richard J.M.; Struijk, Helma; Lugtenberg, R.J.W.; de Jong, Feike; Reinhoudt, David.
In: Chemistry: a European journal, Vol. 2, No. 2, 1996, p. 436-445.Research output: Contribution to journal › Article › Academic › peer-review
TY - JOUR
T1 - 1,3-Alternate calix[4]arenecrown-5 conformers: new synthetic ionophores with better K+/Na+ selectivity than valinomycin
AU - Casnati, Alessandro
AU - Pochini, Andrea
AU - Ungaro, Rocco
AU - Bocchi, Carlo
AU - Ugozzoli, Franco
AU - Egberink, Richard J.M.
AU - Struijk, Helma
AU - Lugtenberg, R.J.W.
AU - de Jong, Feike
AU - Reinhoudt, David
PY - 1996
Y1 - 1996
N2 - New 25,27-dialkoxycalix-[4]arenecrown-5 conformers 8, 10, and 11 have been synthesized and studied. The compounds 8a and 8b, fixed in 1,3-alternate structure, have been obtained in 57 and 40% yield, respectively, by reaction of the corresponding 25,27-dialkoxycalix[4]arenes 7a-b with tetraethylene glycol di-p-toluenesulfonate in the presence of Cs2CO3. The cone 10a and 10b and the partial cone 11 conformers were obtained by selective demethylation of the 25,27-dimethoxycalix[4]arenecrown-5 (6a) and subsequent dialkylation with NaH/DMF and KOtBu/THF, respectively. In the solid state (X-ray), compound 6a adopts a flattened cone conformation, which is also found to be most abundant in CD3CN and CD3OD solution. Upon complexation with potassium picrate compound 6a was converted quantitatively into the 1,3-alternate conformation. All new ligands synthesized were used in the extraction of alkali metal cations from H2O into CHCl3, and as active components in supported liquid membranes and in chemically modified field effect transistors. Results were compared to those obtained with with the natural antibiotic valinomycin 1. All ligands showed high selectivity for potassium. Ligand 8a, fixed in the 1,3-alternate conformation, is more selective than valinomycin and shows the highest K+/Na+ selectivity known so far.
AB - New 25,27-dialkoxycalix-[4]arenecrown-5 conformers 8, 10, and 11 have been synthesized and studied. The compounds 8a and 8b, fixed in 1,3-alternate structure, have been obtained in 57 and 40% yield, respectively, by reaction of the corresponding 25,27-dialkoxycalix[4]arenes 7a-b with tetraethylene glycol di-p-toluenesulfonate in the presence of Cs2CO3. The cone 10a and 10b and the partial cone 11 conformers were obtained by selective demethylation of the 25,27-dimethoxycalix[4]arenecrown-5 (6a) and subsequent dialkylation with NaH/DMF and KOtBu/THF, respectively. In the solid state (X-ray), compound 6a adopts a flattened cone conformation, which is also found to be most abundant in CD3CN and CD3OD solution. Upon complexation with potassium picrate compound 6a was converted quantitatively into the 1,3-alternate conformation. All new ligands synthesized were used in the extraction of alkali metal cations from H2O into CHCl3, and as active components in supported liquid membranes and in chemically modified field effect transistors. Results were compared to those obtained with with the natural antibiotic valinomycin 1. All ligands showed high selectivity for potassium. Ligand 8a, fixed in the 1,3-alternate conformation, is more selective than valinomycin and shows the highest K+/Na+ selectivity known so far.
KW - METIS-105886
KW - IR-10885
U2 - 10.1002/chem.19960020413
DO - 10.1002/chem.19960020413
M3 - Article
VL - 2
SP - 436
EP - 445
JO - Chemistry: a European journal
JF - Chemistry: a European journal
SN - 0947-6539
IS - 2
ER -