Nitrogen Incorporation into Poly(diiododiacetylene) and Attempts Towards Synthesizing Push-Pull Diynes

Cocrystallization is a method employed to orient diynes to achieve the appropriate parameters for topochemical polymerization. Using this technique, poly(diiododiacetylene) (PIDA) and 4-(Iodobuta-1,3-diyn-1-yl)benzoic acid are crystalized into their polymeric forms. The weak C-I bonds in PIDA have shown to break easily with Lewis bases like pyrrolidine and iodide. With the use of multiple deiodinating agents, PIDA has also shown to absorb the heteroatoms of present reducing agents in the final amorphous carbon product. Using sodium azide as a deiodinating agent, it has been theorized that nitrogen would incorporate into PIDA and produce a precursor to a carbon-nitride material based off of previous experiments.;Push-pull diynes are meant to narrow the band gap between a molecule's HOMO and LUMO. Efforts were made to modify the synthesis of the push-pull diyne, 4-(Iodobuta-1,3-diyn-1-yl)benzoic acid. Previous work in the esterification of 4-bromobenzoic acid as well as the Sonogashira coupling reactions on t-butyl 4-bromobonzoate gave unsatisfactory yields. Different halogen moieties as well as different methods of esterification were explored.