The synthesis and characterization of compounds derived from 9,9-dialkylflu
orene and 1,4-dioxane[3,4-b]thiophene are described. The key step involves
a modified Steglich reaction between 9,9-dialkyl-2,7-N,N'-diallyliminochlor
ofluorene or 2,5-N,N'-diallyliminochloroethylenedioxythiophene and tert-BuO
K (Route 1). Route 2 for bis(pyrrol-2-yl)dioxanethiophene, involving the re
action between 1,4-dioxane[2,3-c]thiophene and a dioxolanepropanol, is also
a useful and general strategy. Molecular modeling studies indicate relatio
nships between the molecular parameters (structure, ionization potential, a
tomic charges) of the synthesized moieties and their polymerization propert
ies.