Head-to-Head Linked Double Calix[4]arenes: Convenient Synthesis and Complexation Properties

J Org Chem. 1997 Apr 18;62(8):2487-2493. doi: 10.1021/jo962138z.


Combination of calix[4]arenes functionalized at the upper rim at the 5- and 17-positions with amino and formyl groups, respectively, gives a new series of "head-to-head" linked double calix[4]arenes in nearly quantitative yield. The X-ray structure of a modified double calix[4]arene is reported. The novel, highly preorganized receptor molecules complex silver(I) ions (K(ass) = 9.5 x 10(5) M(-)(1) in CDCl(3)); the selectivity of complexation was studied by supported liquid membrane transport experiments and chemically modified field effect transistor measurements.