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UBC Theses and Dissertations

Synthesis of 2,2’,12,12’-bisdecamethylenedi- (7,17-diethyl-3,8,13,18-tetramethylphorrphine) Hiom, John


The interactions between porphyrins and related tetrapyrrolic macrocycles play many varied and important biological functions. In many of these systems the tetrapyrrolic macrocycles, whilst not covalently linked, are closely associated and the proximity and relative orientations are of critical importance. This thesis describes the synthesis of a covalently bislinked dimeric porphyrin. Our approach consists of constructing a single link first, and building a porphyrin onto either end, simultaneously, in symmetrical fashion via an a,c-biladiene. A variety of methenes were produced to enable the synthesis of porphyrins with reactive side-chains diagonally opposed to the first link. Singly linked porphyrins with C₆, C₈ and C₁₀ chains were produced. The porphyrin side chains were then modified to produce a terminal acetylene diagonally opposed to the first link. The second link was then achieved by an oxidative coupling and catalytic hydrogenation to yield a bislinked porphyrin dimer with two hydrocarbon chains. A model reaction is also described in which a mono-meric porphyrin was dimerised to assess the feasibility of the side chain modification and the final oxidative coupling reaction to produce the singly linked dimer.

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