The homochiral 1-D self-assembly of two classes of [n.n]paracyclophane-tetracarboxamides (pCpTAs) - [2.2]paracyclophane-tetracarboxamide ([2.2]pCpTA) and [3.3]paracyclophane-tetracarboxamide ([3.3]pCpTA) - has been investigated to determine the influence of paracyclophane bridge length on assembly. Both pCpTA families were synthesized and characterized by single-crystal X-ray diffraction, and assemblies of the pCpTAs in solution were examined by NMR, IR, and UV-Vis experiments. These studies reveal that both pCpTA classes assemble according to an isodesmic association model, but that the assembly strength is dependent on paracyclophane structure in subtle ways. The thermodynamic differences between [2.2]pCpTA and [3.3]pCpTA assemblies indicate new ways to probe factors affecting self-complementary assembly by control of intramolecular distances and monomer dynamics.

Structure-property relationship in self-assembling [n.n]paracyclophanes

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.