Abstract
General considerations related to the use of sugars and closely
related compounds as reagents for molecular and macromolecular synthesis
are presented. For the first time, we have used unprotected carbohydrates
to initiate polymerizations. A variety of dicyanoalkenes and -arenes
react with sugars in the presence of alkali to give conjugated polymers.
Both cyclopolymerization and polymerization at only one of two cyano
groups are observed, and some qualitative mechanistic issues related
to these observations are discussed. In some cases, a sugar alkoxide
is the active initiating reagent. Characterization of the resulting
polymers is reported. Alkaline sugar reagents have also been used
in Knoevenagel reactions to synthesize CN-PPV oligomers and a related
conjugated polymer in good yields. The use of the polysaccharide
chitosan as a polycation allows the absorption spectrum of the polythiophene
HPURET to shift to longer wavelengths than other polycations in
electrostatically assembled films.
Key words
polymers - carbohydrates - oligosaccharides - Knoevenagel reactions - polysaccharides - polycations
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