Synthesis and optical properties of polydiacetylenes from dodecahexayne derivatives

Three new dodecahexayne compounds with urethane groups were synthesized and their solid-state polymerization was confirmed to be 1,4-addition to give octatetraynyl- substituted polydiacetylene (PDA) and partially to give a ladder polymer, in which two PDAs were bonded by butadiynylene groups. Though complete conversion to the ladder polymer was not observed, crystallinity of the polymer was preserved. This is due to hydrogen bonding between adjacent molecules or side chains. The (chi) (3) values of the polymerized spincoated films of the urethane- substituted dodecahexayne compounds were evaluated by the THG Maker fringe method. The largest value observed was 2.8 X 10-11 esu for the polymer from 5BCMU-6A at 700 nm.