Rod–coil copolymers from oligo(p-benzamide) foldamers
Self assembling rod–coil copolymers were synthesized in which oligo(p-benzamide) rods up to the octamer were prepared via iterative solution synthesis employing the acid labile 2,4-dimethoxybenzyl amide protective group.
Hairy Aramide Rod−Coil Copolymers
We have synthesized monodisperse “hairy rod oligomers” based on oligo(p-benzamide)s carrying alkyl side chains and conjugated them with polydisperse poly(ethylene glycol) (PEG) chains. The well-defined oligomers were synthesized from 4-amino-2-hexyloxybenzoic acid using a commercial peptide synthesizer. The PEG conjugated hairy rod−coil block copolymers self-assemble in polar and nonpolar organic solvents. The self-organization in solution was investigated by dynamic light scattering (DSL) and transmission electron microscopy (TEM) as a function of solvent, equilibration time, and polarity of the substrate. Individual fibers and fiberlike bundles of aggregates could be observed. As all hydr…
Linear Organo-Soluble Poly(p-benzamide)
Organo-soluble, shape-persistent oligo- and poly(p-benzamide)s were synthesized and characterized. A triethylene glycol (TEG) substituent was introduced to the p-aminobenzoic acid monomer structure as a solubilizing side chain giving 4-amino-2-triethylene glycol benzoic acid. This new monomer was polymerized by the facile polycondensation of the corresponding acid halide derivative of the amine hydrochloric salt. Additionally, a well-defined heptamer was prepared from this monomer on a peptide synthesizer as a model compound. The TEG-substituted oligomers and polymers exhibited good solubility yet high aggregation tendency in common polar and nonpolar organic solvents. The solution self-org…