The first anthracene-containing conjugated polymer, poly(1,4-anthrylen
evinylene) (PAV), was synthesized. Its processability was accomplished
by using the precursor polymer route. Consideration of the mechanism
responsible for the polymerization reaction led to selection of the ad
equate monomer to achieve polymerizability. UV spectra of PAV films sh
owed a band-gap energy 0.3 eV smaller compared to that of poly(phenyle
nevinylene) (PPV) as a result of the minimization of the energy differ
ence between aromatic and quinoid resonance structures by the anthrace
ne unit. Model compound 13 was synthesized to exclude structural defec
ts of PAV as well as to clarify the role of the steric and electronic
effects on the conformation of the main chain. The optical properties
of PAV thin films drastically changed upon reaction with a dienophile
in the solid state.