A method for the synthesis and purification of a homologous series of symmetrical diamido-diacids derived from D-glucaric acid and six alkylenediamines is described. Treating D-glucaro-6,3-lactone with an equimolar amount of lithium acetate dihydrate yielded lithium D-glucarate-6,3-lactone, which in turn was reacted with six alkylenediamines in dimethyl sulfoxide to give the target diamido-diacids. Six new alternating stereoregular polyamides, head, tailtail, head-poly(alkylene D-glucaramides), were then synthesized by simple polycondensation reactions between the activated diamido-diacids [6,6'-(N,N'-alkylene)-bis(D-glucaramid-1-oic acid)s] and the alkylenediamines. Number average molecular weights for the polyamides were estimated by 1 H NMR end group analysis. Models for the three-dimensional shape of these alternating stereoregular polymers were produced from a combination of 1 H NMR data, molecular modeling studies performed on D-glucaramide, and crystal structures of various acyclic D-glucaric acid derivatives.
Derivatives of 3-substituted pyrroles were spread at the air−water interface. Stable films could be
obtained for pyrroles with side chains containing more than 10 carbons. 3-Hexadecanoylpyrrole could not
be polymerized as a monolayer whereas the alkyl derivatives could be polymerized successfully without
having additional monomer in the subphase. The monolayers could be transferred onto hydrophobic
substrates with transfer ratios close to unity. The polymers formed were soluble in chloroform and
tetrahydrofuran. Molecular-weight averages obtained by gel permeation chromatography ranged from
3500 to 6000 when polymerized on ammonium peroxydisulfate and 5000 to 15000 when polymerized on
ferric chloride subphase solutions. 1H NMR indicates that the polymerization is highly regular, leading
to a constitutionally ordered 2,5-poly(3-alkylpyrrole).
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