Studies of polyaza pyrrole-containing systems and linear and macrocyclic polypyrrolic architectures

Pyrrole chemistry is a well-developed area in the field of organic chemistry. Since the beginning of the 20th century this area has developed rapidly, such that pyrrolecontaining compounds have found applications in fields ranging from polymer chemistry to cancer treatment. This dissertation describes the synthesis and properties of a variety of α- aminopyrroles (Chapter 1) and the synthesis of novel pyrrole-based anion receptors. α- Aminopyrroles represent an area of pyrrole chemistry that has not received much attention. This makes such species of academic interest. There is however, an underlying “real world” interest in α-aminopyrroles; such compounds may prove useful in the synthesis of new photosensitizers useful in the area of photodynamic cancer therapy. The second and third chapters present the development of new anion receptors. This area, with more practical applications, is also fundamental in understanding the hostguest interactions involving anionc species and polypyrrolic receptors. In chapter 2 are described open-chain polypyrrolic systems that display a remarkable selectivity for small carboxylate anions relative to larger carboxylate, chloride and dihydrogenphosphate anions. Chapter 3 focuses on the development of hybrid diamido-dipyrromethane macrocyclic systems; these compounds display high selectivity for sulfate over nitrate, making them of interest as possible extractants for use in nuclear waste remediation applications. The determinants of anion selectivity are also addressed in this chapter. Chapter 4 provides experimental methods and characterization data.