gsch_a_1628231_sm1654.pdf (2.17 MB)
p-tert-Butylthiacalix[4]arenes containing guanidinium groups: synthesis and self-assembly into nanoscale aggregates
journal contribution
posted on 2019-06-16, 16:01 authored by Elena A. Andreyko, Joshua B. Puplampu, Patricia A. Ignacio-De Leon, Ilya Zharov, Ivan I. StoikovNew p-tert-butylthiacalix[4]arenes with several different substituents at the lower rim have been synthesised. A method for the selective introduction of one or two guanidinium fragments into the structure of p-tert-butylthiacalix[4]arenes has been developed. The 1,3-alternate thiacalix[4]arenes containing guanidinium groups interact with silver nitrate and oxalic acid in methanol with a logKassoc of about 3.5 and 1:1 stoichiometry, while the macrocycle in the cone conformation interacts with oxalic acid with logKassoc of 7.4 and 2:1 stoichiometry. The new p-tert-butylthiacalix[4]arenes form nanoscale aggregates with hydrodynamic radii of about 70 nm by self-association and by mediation with silver cations and oxalic acid.