1 research outputs found
Bis-TEGylated Poly(<i>p</i>‑benzamide)s: Combining Organosolubility with Shape Persistence
The
synthesis of perfectly planar, bis-substituted aromatic polyamides
is reported herein. With highly flexible triethylene glycol chains
attached and conformational restriction through intramolecular, bifurcated
hydrogen bonds these are among the most shape-persistent yet organo-soluble
polymers to date. Starting from 4-nitrosalicylic acid, our group developed
a route to phenyl-2,5-bis-TEGylated aminobenzoate, which could be
polymerized by addition of lithium bis(trimethylsilyl)amide (LiHMDS).
Since this technique has not been applied to step-growth polycondensations
of polyaramides so far, the influence of two different solvents and
an N-protective group was investigated. Therefore, substituted phenyl
aminobenzoate derivatives carrying a free amine or an N-protective
group have been polymerized. Additionally, the tendency for self-assembly
of the readily soluble bis-TEGylated poly(<i>p</i>-benzamide)
was observed by transmission electron microscopy (TEM) in the dried
state. Dynamic light scattering (DLS) measurements of chloroform solutions
did not indicate the formation of aggregates. Thus, intermolecular
interactions, which other aromatic polyamides typically exhibit, are
prevented. The access to bis-substituted, entirely rigid poly(<i>p</i>-benzamide)s via this new polycondensation method paves
the way for exciting new structures in materials science and supramolecular
chemistry