Stimuli-Responsive Internally Ion-Paired Supramolecular Polymer Based on a Bis-pillar[5]arene Dicarboxylic Acid Monomer

Abstract

A novel bis-pillar[5]arene dicarboxylic acid self-assembles in the presence of 1,12-diaminododecane to yield overall neutral, internally ion-paired supramolecular polymers. Their aggregation, binding mode, and morphology can be tuned by external stimuli such as solvent polarity, concentration, and base treatment.

Supramolecular Amphiphiles Based on Pillar[5]arene and Meroterpenoids: Synthesis, Self-Association and Interaction with Floxuridine

“…The results obtained unambiguously indicate the incorporation of FUDR into the structure of the supramolecular associate 3a/5 . The results obtained are in good agreement with the literature data [ 34 ].…”

Proton transfer mediated recognition of amines by ionizable macrocyclic receptors

“…20). 78 AFM analysis showed a picture more compatible with the presence of linear objects, forming a grid-like pattern with 50–150 nm thick strands, not much different than those seen for the disassembled 43 ·2H/H 2 N(CH 2 ) 12 NH 2 / n -BuNH 2 mixture (Fig. 20).…”

“…20) and DOSY studies – the extensive disassembly of the original polymer, yielding low molecular-weight pillararene/dodecanediamine fragments held together by CH⋯π and weak COO − ⋯H 2 N hydrogen-bond interactions. 78 These data emphasize the critical contribution played by the electrostatic contribution to host–guest complexation provided by the groups ionized by proton transfer.…”

“…74 In vitro studies showed that, after cellular internalization, As a part of our ongoing studies on host-guest-based supramolecular polymers, 75,76 we have recently taken advantage of the proton-transfer mediated recognition strategy to induce the self-assembly of large organized aggregates. 77,78 The successful formation of these polymers relies on dynamic iterative recognition processes between the host and guest monomers. However, when the guest monomer includes a charged group, the counterion often plays a detrimental role on the efficiency of the self-assembly, ion-pairing with the guest moiety and depressing complexation.…”

“…Top: structure of the [44 2- + H 3 N(CH 2 ) 12 NH 3 + ] n supramolecular polymer. Bottom: AFM micrographs demonstrating the disassembly of the polymer by addition of Et 3 N 78.…”