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.