Thesis Title

Synthetic Methods Development For the Construction of Perylene and Fluorenone Derivatives

Date of Graduation

Summer 2008

Degree

Master of Science in Chemistry

Department

Chemistry

Committee Chair

Chad Stearman

Keywords

Perylene derivatives, oxidative coupling, naphthols, triflation, palladium-catalyzed annulations, carbonylation, fluorenones

Subject Categories

Chemistry

Abstract

The overall goal presented in this thesis was to develop efficient synthetic methods and strategies to access versatile organic building blocks for materials synthesis. One type of building block of interest is based on the perylene scaffold. Perylene derivatives exhibit a number of desirable characteristics that include a narrow HOMO-LUMO energy band gap and their ability to be good electron acceptors due to their low reduction potentials and ability to form stable anions. They are also chemically-,thermally-,and photostable. As a result, these compounds have been attractive building blocks for various organic materials. The work presented in this thesis attempts to enable a rapid entry to the perylene scaffold using simple oxidative coupling techniques. The oxidative coupling of 2-naphthol and 2,7-dihydroxynaphthalene were initially explored. A perylene quinone was synthesized in these investigations with a 95% overall yield. Another technique that was explored used a palladium-catalyzed annulation strategy to form a binaphthyl fluorenone that exhibits similar electronic characteristics to perylene derivatives. A new, unpublished palladium-catalyzed annulation was developed in the process for the synthesis of binaphthyl fluorenones in 89% yield. This type of annulation has significant potential for allowing the synthesis of wide range of binaphthyl fluorenone derivatives.

Copyright

© Joshua S. Alford

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