Nanocapsules: Calix[4]arene derivatives that dimerize through ionic interactions in polar solvents

ORGN 365

Josh S. Sasine and Suzanne B. Shuker. Department of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332
Several calix[4]arene derivatives propylated on the lower rim and substituted on the upper rim with various groups have been synthesized. Examples include C-linked-alaninocalix[4]arene, N-linked-alaninocalix[4]arene, anilinocalix[4]arene, amidinocalix[4]arene, aminomethylcalix[4]arene, and carboxycalix[4]arene. Some calix[4]arene derivatives disubstituted on the upper rim in the 1,3 and 2,4 pattern have also been synthesized such as, di-C-linked-glycinodicarboxycalix[4]arene and di-N-linked-glycinodianilinocalix[4]arene along with larger chain amino acids such as beta-alanine and gamma-aminobutyric acid. The self-assembly of these derivatized calixarenes into heterodimers and homodimers has been studied by NMR in polar solvents such as dimethyl sulfoxide and methanol.