Presenter(s): William Edgell − Biochemistry
Faculty Mentor(s): Ramesh Jasti
Poster 69
Research Area: Organic Synthetic Chemistry
Funding: Undergraduate Research Opportunities Program (UROP)
Conjugated polymers possess excellent conductive properties that could facilitate the construction of light weight flexible electronics. This potential application makes an efficient route to conjugated polymers synthetically desirable. The current barrier to large-scale synthesis of these molecules is an inversely proportional relationship between solubility and conductivity. The sought-after conductivity is due to charge transfer across a conjugated π system within the polymer. This affords the polymers with electronic properties atypical of organic molecules. Unfortunately, intermolecular stacking of these π systems leads to poor solubility. Cycloparaphenylenes(CPPs) offer a solution for this conflict between solubility and charge transfer. CPPs are large hoops of strained benzene rings which possess a conjugated π system without a clear avenue for π stacking. A CPP polymer would form a sort of molecular necklace; with large bulky hoops hanging off the polymer backbone, the potential polymers would not stack well with each other, thus reducing chance of aggregation. Utilization of the CPPs as monomers for polymer synthesis could produce a polymer chain with the ideal electrical properties without diminishing the solubility. To this end, this research project focuses on the synthesis of the CPP monomers to be used for the polymer reaction. Creating this highly strained hoop requires a series of reactions to form a string of benzene rings that will be coupled to a single alkyne functionalized benzene. Previous work shows challenges in the route that yields the eight ring CPP. Current work has yielded successful synthesis of functionalized six ring cycloparaphenylene.