The Photochromism of a Diester Linked Bisanthracene

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Thesis type
(Thesis) M.Sc.
Date created
A bisanthracene diester was synthesized in an effort to increase the rate of the anthracene photochemical dimerization. Preliminary reactions of the bisanthracene resulted in the formation of an intramolecular product that cyclizes across the 9, 10, 1’, 4’-position of the anthracenes. This results in an unsymmetrical dianthracene that possesses an isolated alkene group. The research in this thesis describes the photochromic properties of the bisanthracene, as well as studies into the reactivity of the isolated alkene. Different photochromic properties of the bisanthracene were investigated. The optimized conditions were found using a dilute solution in benzene while selectively exciting the bisanthracene. The addition of a peroxycarboxylic acid to the photoproduct resulted in the formation of an epoxide, which caused the intramolecular product to become more photochemically and thermally stable. This resulted in a locked state. Attempts to unlock this system by removal of the epoxide resulted in only low yields of the bisanthracene, but does represent a preliminary gated system for anthracene photochemical reaction.
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Supervisor or Senior Supervisor
Thesis advisor: Williams, Vance
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