18 research outputs found
5,11,17,23-Tetra-tert-butyl-25,27-bisÂ[2-(4-nitroÂphenÂoxy)ethÂoxy]calix[4]arene-26,28-diol acetonitrile tetraÂsolvate
In the crystal structure of the title compound, C60H70N2O10·4CH3CN, the calix[4]arene molÂecule adopts an open-cone conformation with two intraÂmolecular O—Hâ‹ŻO hydrogen bonds. The four benzene rings of the calix[4]arene are twisted to the mean plane defined by four methylÂene C atoms bridging the benzene rings, with dihedral angles ranging from 57.74 (10) to 65.99 (12)°. Two pendant nitroÂphenyl rings are nearly perpendicular to each other, the dihedral angle being 70.9 (3)°. The asymmetric unit of the crystal structure contains four acetonitrile solvent molÂecules, one of which lies in the calix cavity and makes C—Hâ‹ŻĎ€ interÂactions and another links with the calix[4]arene via C—Hâ‹ŻO hydrogen bonding. One tert-butyl group is disordered over two sets of sites, with a 0.736 (13):0.264 (13) occupancy ratio
Tuning and enhancing enantioselective quenching of calixarene hosts by chiral guest amines.
The synthesis of a propranolol amide derivative of p-allylcalix[4]arene is described, which has been designed to behave as a molecular sensor capable of distinguishing chiral amines on the basis of their shape and chirality. This molecule can discriminate between the enantiomers of phenylalaninol through the quenching of the fluorescence emission in methanol in contrast to an (S)-dinaphthylprolinol calix[4]arene derivative, which can discriminate between the enantiomers of phenylglycinol, but not phenylalaninol. The separation between the naphthyl fluorophores and the hydrogen-bonding sites within the chiral cavity can be tuned to recognize guest amines with similar separation between aryl groups and hydrogen-bonding sites. The formation of metal ion complexes of the p-allylcalix[4]arene propranolol amide derivative is shown to induce a more regular and rigid cone conformation in the calix[4]arene macrocycle, which generates a significant enhancement in the observed enantiomeric discrimination