Synthesis and spectroscopic properties of novel B-functionalized 5,10,15,20- tetraarylporphyrins and diporphyrin analogues

Abstract

The objective of this dissertation is to synthesize new porphyrin analogues by peripheral functionalization at B-positions of meso tetraarylporphyrins. These diverse porphyrinic architectures may be useful for various applications, ranging from medicine to molecular device for electron transfer processes. The first chapter of this thesis presents a brief overview on the synthesis of B-functionalized 5,10,15,20 tetraarylporphyrins and their diporphyrin analogues. Chapter 2 describes a novel methodology for the synthesis of a series of B-fused thienoporphyrins and B-substituted porphyrinic thiazolidinone conjugates by using one-pot strategy from 2-formyl-5,10,15,20-tetraarylporphyrins. The detailed synthetic protocol along with the possible mechanistic pathway and spectroscopic characterization of these compounds are discussed in this chapter. Chapter 3 describes an improved and convenient synthetic route for B-azidomethylporphyrins, which have been used as valuable precursors to construct new _-substituted triazolomethylporphyrins and , meso-triazolo methyl-bridged porphyrin analogues through copper(I)-catalyzed Huisgen 1,3-dipolar reaction. The syntheses, characterization and preliminary photophysical properties of these compounds are discussed in this chapter. Chapter 4 focuses on the design and synthesis of novel B, B-linked diporphyrin-1,2,3-triazole conjugates in which porphyrin macrocycle is covalently linked to a 1,2,3-triazole ring system. These novel hybrid molecules may have potential to be used as photodynamic agents in photodynamic therapy applications.