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Bis-TEGylated Poly(p‑benzamide)s: Combining Organosolubility with Shape Persistence

Type of publication Peer-reviewed
Publikationsform Original article (peer-reviewed)
Publication date 2013
Author Schulze Maren, Michen Benjamin, Fink Alke, Kilbinger Andreas F.M.,
Project Functional nanoscopic objects via polymerisation of sequence-controlled oligoaramides
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Original article (peer-reviewed)

Journal Macromolecules
Volume (Issue) 46(14)
Page(s) 5520 - 5530
Title of proceedings Macromolecules
DOI 10.1021/ma4010023


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(p-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(p-benzamide)s via this new polycondensation method paves the way for exciting new structures in materials science and supramolecular chemistry.