Synthesis Of Asymmetric Porphyrin And Antibacterial Activity Of Porphyrin-Based Honeycomb Films

Porphyrins are a group of heterocyclic macrocyclesconsisting of four modified pyrrole subunits linked via methine bridges (=CH-).They have been playing very important roles in nature, such as chlorophyll in green plants and hemoglobin in our blood. Besides their natural role, porphyrins are currently employed as platforms for study of theoretical principles and applications in a wide variety of fields including chemistry, biology, medicine, geology, material science and so on.In chapter one, firstly, a brief introduction of porphyrins which include the structures, physicochemical property, aggregates, and synthetic methods are outlined. Then Supermolecular self-assembly behavior of porphyrins on the interface is discussed. At last, we summarize the applications of porphyrins in diffident fields.In chapter two, micrometer-sized porous honeycomb-patterned thin films based on hybrid complexes formed via electrostatic interaction between Mn(Ⅲ) meso-tetra(4-sulfonatophenyl) porphine chloride (an acid form,{MnTPPS}) and dimethyldioctadecylammonium bromide (DODMABr). The morphology of the microporous thin films can be well regulated by controlling the concentration of MnTPPS-DODMA complexes, DODMABr, polystyrene (PS), and solvents, respectively. The morphology of the microporous films were characterized by OM, AFM and SEM observations, the photophysical property was characterized by UV-vis measurement and the hydrophobic property was studied by water contact angle experiment.In chapter three, we studied the antibacterial activity of the honeycomb films by antibacterial experiment. Porphyrins are commonly used as photosensitizers to produce reactive oxygen species, in particular, singlet oxygen, which causes photodynamic inactivation (PDI) of microorganisms upon exposing to visual light in the presence of oxygen. Through antibacterial experiment, the honeycomb films were found to have efficient antibacterial activities under visual light. These results indicate that porphyrin-based honeycomb films can serve as interesting and promising photodynamic surface to inactivate microorganisms. Such materials have great potentials in medical industrial and household environmental applications.In chapter four, a concise synthetic method to prepare Push-Pull dibenzoporphyrins from tetraarylporphyrin is reported in this thesis. A vicinal two-fold Heck reaction was carried out on dibromoporphyrins with alkenes. The introduction of alkenyl groups through the vicinal2-fold Heck reaction,6-π-electrocyclisation and subsequent aromatization occurred in one pot. We were successful in conveniently introducing push group and pull group at the β-position of tetraarylporphyrin. Due to the extension in the π-conjugation, the push-pull π extended porphyrin displayed much broadened and bathochromic shifted UV-vis absorptions, as compared with the starting porphyrin. To this end, push-pull type porphyrins are interesting.