Synthesis of Bipyridine-Derived Ligands for DNA Binding and Shape Switching

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Li, Xue
DNA bending , Pyrene , 2, 2'-bipyridine
The objective of this project is synthesizing bipyridine-derived ligands in order to study DNA conformational bending. The synthesis of bipyridine derivatives has been investigated. 6,6’-Dibromo-2,2’-bipyridine and small scale of 6,6’-diformyl-2,2’-bipyridine have been successfully synthesized in the laboratory. The ynthesis of large amount of a direct precursor to 6,6’-diformyl-2,2’-bipyridine in an multiple step way has been achieved. The synthesis of mono functionalized pyrene derivatives and of 1,6-dissymmetrically functionalized pyrene derivatives has been heavily studied. Successfully methods have been reported in this thesis. The complete assembly of bipyridine and pyrene units into the final ligands and their model has also been studied. Palladium borylation and Suzuki-Miyaura cross-coupling have been used to successfully connect the bipyridine with pyrene units. In addition to Suzuki-Miyaura methodology, the direct coupling of N,N’-dioxide-2,2’-bipyridine with aromatic bromides under palladium catalysis has been investigated. This method could be an alternative way to access to mono-substituted 6-bipyridines, symmetrically or even asymmetrically 6,6’-disubstituted-2,2’-bipyridine derivatives.
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