Download Poster (1.1 MB)
Benziporphyrins 1 are nonaromatic porphyrinoids with a cross-conjugated 6π electron arene subunit. However, modification of this system can result in the formation of aromatic macrocycles. In this project, a benziporphyrin-like system 2 incorporating a phenalene subunit has been targeted for investigation. It is anticipated that this porphyrinoid will take on fully aromatic characteristics while retaining a fused naphthalene moiety. The required precursors to 2 are tripyrranes such as 3a and 3b, and tricyclic dialdehydes 4 or 5. Initial attempts to prepare 4 by performing a Wittig condensation with perinaphthenone, followed by a Vilsmeier formylation, were unsuccessful. Currently, an alternative synthetic route to 5 is being developed beginning with 1-tetralone. Naphthylsuccinic anhydride 6 has been prepared and cyclized to produce keto acid 7a. It is anticipated that esterification to produce 7b, followed by a Wittig condensation and reduction with DIBAL-H, will afford the required dialdehyde 5. Subsequent ‘3+1’ condensation with tripyrranes 3 will the afford phenaliporphyrins 2.
Mathius, Melissa, "Investigations into the Synthesis of Phenaliporphyrins" (2020). Chemistry. 3.