Biomedically Relevant Applications of Bolaamphiphiles and Bolaamphiphile-Containing Materials.

Bolaamphiphiles (BAs) are structurally segmented molecules with rich assembly characteristics and diverse physical properties. Interest in BAs as standalone active agents or as constituents of more complex therapeutic formulations has increased substantially in recent years. The preorganized amphiphilicity of BAs allows for a range of biological activities including applications that rely on multivalency.

Role of Acid in the Co-oligomerization of Formaldehyde and Pyrrole.

Building on previous work ( 8154-8166) under neutral conditions, we examined the co-oligomerization of CHO and pyrrole to form porphryinogen under acidic conditions using density functional theory (B3LYP//6-311G**). Thermodynamically, we found that azafulvene intermediates were significantly stabilized under highly acidic conditions. Kinetically, energy barriers were lowered for C-C bond formation, discriminating in favor of reactions that lead to porphyrinogen.