Single Crystal to Single Crystal Polymerization of a Columnar Assembled Diacetylene Macrocycle

Organic tubular materials have attracted lots of attentions for their potential applications as nanoscale fluidic transport systems, specific ion sensors, molecular sieves and confined molecular reaction containers. While conjugated polymers, due to delocalized Pi electrons, exhibit interesting solar cells and sensors applications. In this thesis, we developed a conjugated polymer which combines the attributes of conjugated polymers with tubular materials, which should have great potential to work as a sensing material. We reproduced and scaled-up the synthesis of a polymerizable macrocycle 1 that contains two rigidly separated diacetylene units. We found that, through hydrogen bonding, 1 can assemble into columnar crystals and can be polymerized under a single crystal to single crystal transformation process to afford porous polydiacetylene (PDA) crystals. We studied the assembly of the macrocycles 1 under different conditions to give three different crystalline forms and micro-phase crystals, and also investigated their subsequent polymerizations. The macrocycle assembly and polymerized materials were characterized by a variety of technique. Since the gas adsorption measurement exhibited PDA crystals still retained its porosity and the polymer should have ability to uptake suitable guest molecules, therefore the absorption of iodine for PDA crystals was investigated as well