Comparative Investigation of Coupling Methods to Create 2,2'-Bipyridine Adducts
Abstract
The project aims to streamline the synthesis of 2,2’-bipyridine adducts, so they can be efficiently synthesized as precursors for ligands in novel organometallic ruthenium complexes. Specifically, the compounds being synthesized are 4,4’-methylated, 4-methylated, 5,5’-methylated, and 5-methylated, 2,2’-bipyridines. Three different synthetic methods will be explored including homo-coupling and crosscoupling reactions as well as the use of a turbo-Grignard reagent. The homo-coupling reaction with or without the turbo-Grignard reagent uses 2-bromo-4-methyl or 2-bromo-5-methyl pyridine as the starting material to produce the 4,4’-methylated adduct or 5,5’-methylated adduct respectively. This is in contrast to the cross-coupling reaction which utilizes a combination of the 2-bromo-4-methyl pyridine and trimethylstannyl-pyridine or 2-bromo-5-methyl pyridine and trimethylstannyl-pyridine to produce either the 4-methylated or 5-methylated adduct. The methodology has been developed to ensure an airfree environment by assembling the closed reaction chamber in a nitrogen glovebox. The reaction is completed on a Schlenk-line assembly under inert argon atmosphere and is monitored by TLC. The product is isolated and purified via extraction and sublimation. Compound characterization is carried out utilizing NMR and FT-IR. The bipyridine building blocks, based on their excellent bidentate ligands with complexing abilities, will be incorporated into ruthenium complexes in a collaborative project, increasing the photosensitivity of these complexes, opening the doors for many applications ranging from synthetic photovoltaics to anti-cancer activity.
Faculty Sponsors
Dr. Beatrix Aukszi
Project Type
Event
Location
Alvin Shermany Library
Start Date
4-5-2019 1:00 PM
End Date
4-5-2019 5:00 PM
Comparative Investigation of Coupling Methods to Create 2,2'-Bipyridine Adducts
Alvin Shermany Library
The project aims to streamline the synthesis of 2,2’-bipyridine adducts, so they can be efficiently synthesized as precursors for ligands in novel organometallic ruthenium complexes. Specifically, the compounds being synthesized are 4,4’-methylated, 4-methylated, 5,5’-methylated, and 5-methylated, 2,2’-bipyridines. Three different synthetic methods will be explored including homo-coupling and crosscoupling reactions as well as the use of a turbo-Grignard reagent. The homo-coupling reaction with or without the turbo-Grignard reagent uses 2-bromo-4-methyl or 2-bromo-5-methyl pyridine as the starting material to produce the 4,4’-methylated adduct or 5,5’-methylated adduct respectively. This is in contrast to the cross-coupling reaction which utilizes a combination of the 2-bromo-4-methyl pyridine and trimethylstannyl-pyridine or 2-bromo-5-methyl pyridine and trimethylstannyl-pyridine to produce either the 4-methylated or 5-methylated adduct. The methodology has been developed to ensure an airfree environment by assembling the closed reaction chamber in a nitrogen glovebox. The reaction is completed on a Schlenk-line assembly under inert argon atmosphere and is monitored by TLC. The product is isolated and purified via extraction and sublimation. Compound characterization is carried out utilizing NMR and FT-IR. The bipyridine building blocks, based on their excellent bidentate ligands with complexing abilities, will be incorporated into ruthenium complexes in a collaborative project, increasing the photosensitivity of these complexes, opening the doors for many applications ranging from synthetic photovoltaics to anti-cancer activity.
