2011 - 20th Annual NC State Undergraduate Research Spring Symposium

This research focused on the synthesis, characterization and metalation of variable sizes of cpp. The method employed for this research follows a ground-up synthesis for cpp. In this scheme, an L-shaped, cyclohexyl-based unit is polymerized into a square-shaped macrocycle through a nickel coupling reaction. This macrocycle is then aromatized to yield cpp in ~5% yield. Macrocyclization of the L-unit alone yielded [9], [12], [15], and [18] cpp. Adding p-dihalophenyls to the nickel coupling step yielded variable sized CPP from [8]-[18]. The products of the macrocycle aromatization were difficult to work up and purify, so a different route was tested. Based off perviously published findings, a system of selenium dioxide and trimethylsilyl polyphosphate can be used to aromatize compounds. The results of this method were not available at this time, however initial findings were promising.

The final component of the research was metalation of cpp. Metalation of cpp would give the molecule more controlled electronic properties. Chromium, Molybdenum and Tungsten hexacarbonyls were used to metalate cpp. The metalation reactions were carried out in a CEM microwave and the products were identified with IR spectroscopy. Cpp was successfully metalated with Cr(CO)_6.