Tuesday, June 19, 2007 - 2:15 PM
The Merlins (Boise Centre on the Grove)

Synthesis and Studies of a Novel Tripyrrole

Steven D. Roth and David A. Lightner. University of Nevada, Reno, NV

2,3,7,8,12,13-hexa-ethyltripyrrin-1,14-dione (1) is a novel compound based on the skeleton of natural occurring tripyrroles. These compounds are the result of less common degradation pathways of bilirubin-IXα in the body. The synthesis of 1 is shown as well as its unusual properties as a helical shaped, hydrogen bonded dimer in the crystal. More specifically the hydrogen bonding motif is a new take on a long known non-covalent interaction seen in similar molecules known as dipyrrinones. Due to a deviation from Beer's Law, 1 is believed to be in dimer equilibrium in non-polar solutions. Interestingly, this molecule changes color from yellow to orange depending on the solvent. For greater color changes the addition of neat base (DBU) or neat acid (TFA) was used to give color changes through chemical reaction.