Cavity-containing aromatic oligoamide foldamers and macrocycles: progress and future perspectives

Abstract

As a major class of foldamers, aromatic oligoamide foldamers have attracted intense interest. The rigidity of aromatic residues and amide linkages allows the development of foldamers with readily predictable, stable...

High-Molecular-Weight Poly(aromatic amide) Foldamers via Living Polymerization

“…These supramolecular structures may be polymer fibrils with the low- q power-law scattering following q –2.3 in THF and q –1.8 in DMF, representing theta solvent and good solvent conditions, respectively . A solvent like DMF is well known to effectively interrupt the interchain aggregation of aromatic oligoamide foldamers such as macrocycles and helices. , We believe that similarly, in the case of P13 in DMF, the supramolecular aggregation of the helices is at least partially disrupted.…”

Self-assembled Macrocycles: Design Strategies and Emerging Functions

“…Those have been used for different purposes, such as molecular recognition, ion transport, supramolecular catalysis, and other soft materials . Gong and co-workers have developed a series of aromatic oligoamide macrocycles of different sizes over the last one and a half decades. ,, They reported a tri­(ethylene glycol)­monomethyl ether modified macrocycle ( 7a , Figure a) which self-assembled into a well-defined spherical nanostructure with an average diameter of 3.04 μm from a dichloromethane (DCM)/ p -xylene mixture. , However, the aggregation morphology depends on the solvent polarity, and it was established by changing p -xylene with polar solvents, such as methanol or acetonitrile; the self-assembly leads to a film-like structure instead. A year later, they introduced a relatively more nonpolar solubilizing side chain to the n -octyl or n -dodecane group that induced strong aggregation of the macrocycles to nanotubular stacks ( 7b – d , Figure b) .…”

“…The self-assembly process of this class of macrocycles is initiated by the strong intermolecular π−π stacking interaction, and some weak intermolecular H-bonding interaction. 24,48 Since the initial report of such macrocycles in 2004, several new systems have been developed so far. Those have been used for different purposes, such as molecular recognition, ion transport, supramolecular catalysis, and other soft materials.…”

“…49 Gong and co-workers have developed a series of aromatic oligoamide macrocycles of different sizes over the last one and a half decades. 24,48,50 They reported a tri(ethylene glycol)monomethyl ether modified macrocycle (7a, Figure 4a) which self-assembled into a well-defined spherical nanostructure with an average diameter of 3.04 μm from a dichloromethane (DCM)/p-xylene mixture. 51,52 However, the aggregation morphology depends on the solvent polarity, and it was established by changing p-xylene with polar solvents, such as methanol or acetonitrile; the self-assembly leads to a film-like structure instead.…”

“…Unlike the larger macrocycles, where substantial flexibility forces the molecules out of planarity, smaller macrocycles are predominantly planar, generally reinforced by the interior and exterior H-bonding interactions. The self-assembly process of this class of macrocycles is initiated by the strong intermolecular π–π stacking interaction, and some weak intermolecular H-bonding interaction. , Since the initial report of such macrocycles in 2004, several new systems have been developed so far. Those have been used for different purposes, such as molecular recognition, ion transport, supramolecular catalysis, and other soft materials .…”