Supramolecularly Engineered Amphiphilic Macromolecules: Molecular Interaction Overrules Packing Parameters.

We report molecular interaction-driven self-assembly of supramolecularly engineered amphiphilic macromolecules (SEAM) containing a single supramolecular structure-directing unit (SSDU) consisting of an H-bonding group connected to a naphthalene diimide chromophore. Two such SEAMs, P1-50 and P2-50, having the identical chemical structure and hydrophobic/hydrophilic balance, exhibit distinct self-assembled structures (polymersome and cylindrical micelle, respectively) due to a difference in the H-bonding group (hydrazide or amide, respectively) of the single SSDU. When mixed together, P1-50 and P2-50 adopted self-sorted assembly.

pH-Triggered Sustained Drug Delivery from a Polymer Micelle having the β-Thiopropionate Linkage.

The synthesis, micellar aggregation, and pH-triggered intracellular drug delivery ability of an amphiphilic statistical copolymer (P2) are studied. Two methacrylate derivatives, one containing a hydrophilic pendant and the other containing a hydrophobic pendant chain, are copolymerized to produce P2. The hydrophobic pendant chain is linked to the polymer backbone by a β-thiopropionate linkage, known to undergo slow hydrolysis at mild acidic pH.