In: Polymer Chemistry, 2019, vol. 10, no. 16, p. 2057–2063
This paper deals with the synthesis and investigation of comb-like poly(norbornene)s carrying lateral rod-like aramid groups. Two types of norbornene-based monomers were synthesized and copolymerized with a norbornene carrying an aliphatic side chain using ring opening metathesis polymerization (ROMP). The new monomers contain aramid derivatives that display different types of non-covalent...
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In: Macromolecules, 2018, vol. 51, no. 11, p. 4363–4369
Well-defined telechelic poly(benzamide)s were synthesized by chain-growth polycondensation of phenyl-4-amino benzoate and pentafluorophenyl-4-amino benzoate derivatives with a bifunctional initiator in the presence of LiTMP as base. The polymerization was carried out at −70 °C to prevent self-initiated polymerization. To confirm the control over molecular weight, different defined...
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In: Structural Chemistry, 1997, vol. 8, no. 6, p. 435-441
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In: Macromolecules, 2017, vol. 50, no. 11, p. 4188–4197
The polymerization of aromatic para-amino acid ester derivatives was studied using model compounds. Mechanistic and kinetic experiments led to the discovery of some side reactions. Finally, high molecular weight poly(p-benzamide)s were synthesized and characterized. The use of highly reactive pentafluorophenol ester lead to polymers up to molecular weights of around 50 000 Da....
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In: Journal of Polymer Science Part A: Polymer Chemistry, 2016, p. -
Herein we present the synthesis and polycondensation of mono- and di-N-protected, bis-substituted tri(benzamide)s with the aim to create large, tubular helices. We synthesized 2,4-dimethoxy and 2,5-bis-TEGylated aminobenzoic acid derivatives as bent and linear monomers and introduced p-methoxybenzyl (PMB) amide protecting groups to the oligobenzamide backbone. An iterative coupling strategy...
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In: Journal of the American Chemical Society, 2014, vol. 136, no. 37, p. 12832–12835
Macrocyclizations in exceptionally good yields were observed during the self-condensation of N-benzylated phenyl p-aminobenzoates in the presence of LiHMDS to yield three-membered cyclic aramides that adopt a triangular shape. An ortho-alkyloxy side chain on the N-benzyl protecting group is necessary for the macrocyclization to occur. Linear polymers are formed exclusively in the absence of this...
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In: CHIMIA International Journal for Chemistry, 2013, vol. 67, no. 11, p. 788–790
We present the solid-supported synthesis of a linear rigid rod-like tetradeca(p-benzamide) nanorod as well as a pentadeca( p -benzamide) nanorod carrying an amide N-hexyl side chain at the center of the rod (on the 8th amino acid of the molecule). These nanorods were conjugated with solubilizing poly(ethylene glycol) chains and their solution aggregation was investigated. Both rod–coil block...
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In: Macromolecules, 2013, vol. 46, no. 14, p. 5520–5530
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...
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In: ACS Nano, 2013, vol. 7, no. 6, p. 5491–5498
Molecular self-assembly on surfaces is dictated by the delicate balance between intermolecular and molecule–surface interactions. For many insulating surfaces, however, the molecule–surface interactions are weak and rather unspecific. Enhancing these interactions, on the other hand, often puts a severe limit on the achievable structural variety. To grasp the full potential of molecular...
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In: The Journal of Physical Chemistry A, 2012, vol. 117, no. 3, p. 616–625
Stacked dimers of four polycondensed aromatic hydrocarbons, with structures varying from high to reduced symmetries, have been calculated with dispersion-corrected density functional theory. The configurations of the stacked dimers are readily classified by two in-plane displacements and a relative rotation. The potential energy surface in these three coordinates was calculated with rigid...
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