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This project was aimed at synthesising, characterising and examining the properties of the novel polyamine ligand 4’-{2’”-(12-Amino-2,6,9-triazadodecyl)-phenyl}-2,2’:6’,2”-terpyridine and its related complexes. The ligand would be based around the 4’-(o-toluyl)-2,2’:6’,2”-terpyridine framework and have potential applications in analytical chemistry. The 4’-(o-toluyl)-2,2’:6’,2”-terpyridine framework would have a tail attached on the functionalised o-toluyl methyl group. The ortho toluyl functionality was chosen so that the donor atom containing tail would be directed back towards the coordination site. This would make it easier for the tail to interact with a central metal ion. There is potential to be able to change the number and type of donor atom in the tail so that the ligand may be metal ion selective. As the tail would contain donor atoms, the denticity of the ligand would be increased making it more applicable for complexometric titrations. The 2,2’:6’,2” terpyridines exhibit strong colours when coordinated to selective metal ions and so would have potential applications in colorimetry also. The ligand was successfully synthesised and characterised. In a multi-step process, the 4’-(o-toluyl)-2,2’:6’,2”-terpyridine underwent radical bromination before the tail was attached. The tail used in this research was N,N'-bis (3-aminopropyl)ethane-1,2-diamine (3,2,3-tet). The secondary amines in this polyamine tail were protected before addition to the brominated 4’-(o-toluyl)-2,2’:6’,2”-terpyridine to ensure terminal addition. After the tail addition, a two step separation process purified a sample of 4’-{2’”-(12-Amino-2,6,9-triazadodecyl)-phenyl}-2,2’:6’,2”-terpyridine for analysis. Due to the late stage in this research where a successful separation technique was found, little work was done on examining the properties of this ligand and its complexes.

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This project was aimed at synthesising, characterising and examining the properties of the novel polyamine ligand 4’-{2’”-(12-Amino-2,6,9-triazadodecyl)-phenyl}-2,2’:6’,2”-terpyridine and its related complexes. The ligand would be based around the 4’-(o-toluyl)-2,2’:6’,2”-terpyridine framework and have potential applications in analytical chemistry. The 4’-(o-toluyl)-2,2’:6’,2”-terpyridine framework would have a tail attached on the functionalised o-toluyl methyl group. The ortho toluyl functionality was chosen so that the donor atom containing tail would be directed back towards the coordination site. This would make it easier for the tail to interact with a central metal ion. There is potential to be able to change the number and type of donor atom in the tail so that the ligand may be metal ion selective. As the tail would contain donor atoms, the denticity of the ligand would be increased making it more applicable for complexometric titrations. The 2,2’:6’,2” terpyridines exhibit strong colours when coordinated to selective metal ions and so would have potential applications in colorimetry also. The ligand was successfully synthesised and characterised. In a multi-step process, the 4’-(o-toluyl)-2,2’:6’,2”-terpyridine underwent radical bromination before the tail was attached. The tail used in this research was N,N'-bis (3-aminopropyl)ethane-1,2-diamine (3,2,3-tet). The secondary amines in this polyamine tail were protected before addition to the brominated 4’-(o-toluyl)-2,2’:6’,2”-terpyridine to ensure terminal addition. After the tail addition, a two step separation process purified a sample of 4’-{2’”-(12-Amino-2,6,9-triazadodecyl)-phenyl}-2,2’:6’,2”-terpyridine for analysis. Due to the late stage in this research where a successful separation technique was found, little work was done on examining the properties of this ligand and its complexes.

Thesis advisor: Larry W. McLaughlin / There are two major goals for my project. The first is to create and characterize metal-ligand-DNA complexes that could be synthesized using traditional organic methods followed by solid phase techniques. The second is to demonstrate that these complexes with complementary DNA sequences could self-assemble into higher-ordered structures. In order to generate supramolecular DNA-metal structures such as cubic lattices, it is necessary to create an octahedral metal-ligand center tethering six DNA arms as a building block. The Iron/Ru (II) bis(2,2':6',2''terpyridine) derivatives were chosen because: (i) the complex is well known to present octahedral geometry; (ii) the coordination is very stable; and (iii) while previous work required the solid-phase synthesis of six DNA arms simultaneously--an inefficient process--by using terpyridine ligands we need only extend three arms at once. Thus, several terpyridine-linker compounds were synthesized via two different routes. A DNA 14mer was synthesized afterwards by "Reverse Coupling Protocol" on a solid phase synthesizer and the terpyridine was connected to it followed by elongation of the rest two DNA arms. The DNA-terpyridine complexes were evaluated by stepwise hybridization tests and gel electrophoresis with or without the assistance of radio labeling. In addition, the assembly of metal with the terpyridine-DNA complex was also characterized by adding different metal ions such as Iron (II) and Ru (II) to the complex. Various buffer conditions were applied in constructing those conjugates in order to help forming branched DNA-ligand-metal complexes with higher molecular weight. / Thesis (MS) — Boston College, 2010. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.

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