Synthesis of methoxy benzodipyrrole

Abstract

Benzodipyrroles are aromatic heterocyclic that have elicited considerable interest in various fields of chemistry, for example in the development of ionophores for oxanions,2 antitumor drugs,3 and as semiconductive materials.8,9 The use of benzodipyrroles has been widely explored in the treatment of several kinds of infectious diseases.3 In addition, these molecules have been seen to serve as effective precursors to porphycenes, which are potential photosensitizers for photodynamic therapy. The study of a promising class of photosensitizers, called dibenzoporphycenes, has been limited due to their difficult synthesis and low solubility.4 Hence, the synthesis of new benzodipyrrole for the synthesis of more soluble benzoporphycenes is needed. This thesis describes the synthesis and characterization of the more soluble dimethoxybenzodipyrrole. The synthesis of methoxy benzodipyrroles was straightforward, clean and had a workable level of solubility in organic solvents. However, dimethoxy benzodipyrrole was obtained in modest yields (~ 8%). This compound appears to be a viable precursor for future synthesis of dibenzoporphycenes.