Saturday, November 30, 2013

Dr. Huggins - Dipyrrinone

         Dr. Huggins gave a seminar on November 22 on the main topic of Dipyrrinones. This was his main subject since he works with undergrads at the University of West Florida on Dipyrrinones. From what I could gather, his goal with the undergrads is to be able to synthesize Dipyrrinones and interrupt their stability, primarily through the use of amides. However, listening to Dr. Huggins, it was very clear that amides are a pain in the neck to work with. One student offered an alternative to amides, but Dr. Huggins stated that the goal is mass production of Dipyrrinones for undergrads, and that while other compounds would certainly work, they were too costly.  In his studies, a synthesis of Dipyrrinone was found  to be possible with amides in one way, but it was still a very messy process.
         The reason for the failure of multiple Dipyrrinone syntheses inlcuded self-association, because Dipyrrinone tends to bond with itself. However, KOH and CH3OH can form 88% Dipyrrinone that has a planar confirmation. Also, Dipyrrinone has very strong hydrogen bonds, so steric interactions are required to interrupt self-association. Amides yielded horrible results in percentage Dipyrrinone formed if at any was formed at all. Pyrole Sulfonamide also yielded horrible results, particularly due to the humidity of Florida since immediate dryness is required in end procedure for decent results. Amides also failed in adjusting solubility in Bis-Dypirrinones since trans amidation happens immediately in the reaction process.
          While Dr. Huggins never got the result he purposefully tried to accomplish, he was able to form helpful compounds by accident in the process. The chemicals made in this process are all highly fluorescent, so thankfully the Dipyrrinone research is useful in other ways than intended.

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