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Bis-TEGylated poly(p-benzamide)s: combining organosolubility with shape persistence

  • Schulze, Maren Department of Chemistry, University of Fribourg, Switzerland
  • Michen, Benjamin Adolphe Merkle Institute, University of Fribourg, Switzerland
  • Petri-Fink, Alke Department of Chemistry, University of Fribourg, Switzerland - Adolphe Merkle Institute, University of Fribourg, Switzerland
  • Kilbinger, Andreas F. M. Department of Chemistry, University of Fribourg, Switzerland
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    23.07.2013
Published in:
  • Macromolecules. - 2013, vol. 46, no. 14, p. 5520–5530
English 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.
Faculty
Faculté des sciences et de médecine
Department
Département de Chimie
Language
  • English
Classification
Chemistry
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https://folia.unifr.ch/unifr/documents/303206
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