Silver's Effect On Porphyrin
Introduction Tetraphenylporphyrin will be synthesized and metallated with silver acetate. After purification and NMR and UV-visible spectra was taking for the original porphyrin synthesized and the silver porphyrin. From this data obtained we will talk about silver’s effect on porphyrin.
Theory
Porphyrin is important to study because it plays keys roles in biological process; they are responsible for giving plants and blood their colors green and red respectively. Porphyrins have the iron chelate in hemoglobin and myoglobin for carrying oxygen. Metallated porphyrins and their other forms are also evident in cytochrome c which is an important aspect to the electron transport chain and vitamin B12 which is used keep the body’s nerve, make DNA, …show more content…
For instance non-metallated porphyrin exhibits a deep purple color, but after metalation different physical properties become amended. In this case more specifically silver will produce a less stable porphyrin a different yet similar color to porphyrin. Figure 2 shows the structure of unmetallated and metallated porphyrin. Figure 2. Chemical tructures of, H2TPP (A) & metallated tetraphenylporphyrins, (B).
The Adler-Longo method will be used to synthesize tetraphenylporphyrin. This method includes pyrrole and benzaldehyde heated in propionic acid which is conveyed in first reaction scheme. The expected yield range for this experiment is around 10-20 percent.
Reaction Scheme 1 Metalation is done by heating the metal salt in a distillation tube until it refluxes in DMF which is shown in the second scheme. The silver metal has +2 oxidation state and is stabilized with the porphyrin, but it is light sensitive so experimentation will have to be carried out in the dark.
Reaction Scheme …show more content…
The energies effect metal dp orbitals that possess the same symmetry. Dxz a Dyz have the egp symmetry which have the ability to overlap eg(p*). This effect is similar to pi backbonding where the electron density is donated by a metal to a ligand with p* orbitals. When these orbitals interact with each other, porphyrin eg(p*) orbitals are lowered in energy, but metal dp orbtials are raised in energy due the orbitals having the same symmetry. This is evident when the Q and Soret bands shift on the UV-vis spectrum. MTPP compounds are also known as hyper porphyrins because they are less than half way filled. Hyper porphyrins show additional bands around 320 – 420 nm which occur under charge transfer transition between the porphyrin and metal. Figure 4.
In contrast, the later d-block metal d orbitals are filled and have lower energy than the porphyrin eg(*) orbitals. Again, these orbitals interact, but the porphyrin eg(*) orbitals are raised in energy and the metal d orbitals are lowered in energy (Fig. 4B). This results in shifting the Soret and Q bands to higher energies. These are referred to as hypso porphyrins and tend to contain metals from later in the d-block which are more than half filled (d6 – d9) such as Ni(II), Pt(II) and Pd(II). Thus the energies of the Soret and Q bands can be correlated with the position of the metal in the periodic table.
Experimental Procedure
Theory
Porphyrin is important to study because it plays keys roles in biological process; they are responsible for giving plants and blood their colors green and red respectively. Porphyrins have the iron chelate in hemoglobin and myoglobin for carrying oxygen. Metallated porphyrins and their other forms are also evident in cytochrome c which is an important aspect to the electron transport chain and vitamin B12 which is used keep the body’s nerve, make DNA, …show more content…
For instance non-metallated porphyrin exhibits a deep purple color, but after metalation different physical properties become amended. In this case more specifically silver will produce a less stable porphyrin a different yet similar color to porphyrin. Figure 2 shows the structure of unmetallated and metallated porphyrin. Figure 2. Chemical tructures of, H2TPP (A) & metallated tetraphenylporphyrins, (B).
The Adler-Longo method will be used to synthesize tetraphenylporphyrin. This method includes pyrrole and benzaldehyde heated in propionic acid which is conveyed in first reaction scheme. The expected yield range for this experiment is around 10-20 percent.
Reaction Scheme 1 Metalation is done by heating the metal salt in a distillation tube until it refluxes in DMF which is shown in the second scheme. The silver metal has +2 oxidation state and is stabilized with the porphyrin, but it is light sensitive so experimentation will have to be carried out in the dark.
Reaction Scheme …show more content…
The energies effect metal dp orbitals that possess the same symmetry. Dxz a Dyz have the egp symmetry which have the ability to overlap eg(p*). This effect is similar to pi backbonding where the electron density is donated by a metal to a ligand with p* orbitals. When these orbitals interact with each other, porphyrin eg(p*) orbitals are lowered in energy, but metal dp orbtials are raised in energy due the orbitals having the same symmetry. This is evident when the Q and Soret bands shift on the UV-vis spectrum. MTPP compounds are also known as hyper porphyrins because they are less than half way filled. Hyper porphyrins show additional bands around 320 – 420 nm which occur under charge transfer transition between the porphyrin and metal. Figure 4.
In contrast, the later d-block metal d orbitals are filled and have lower energy than the porphyrin eg(*) orbitals. Again, these orbitals interact, but the porphyrin eg(*) orbitals are raised in energy and the metal d orbitals are lowered in energy (Fig. 4B). This results in shifting the Soret and Q bands to higher energies. These are referred to as hypso porphyrins and tend to contain metals from later in the d-block which are more than half filled (d6 – d9) such as Ni(II), Pt(II) and Pd(II). Thus the energies of the Soret and Q bands can be correlated with the position of the metal in the periodic table.
Experimental Procedure