Phthalocyanines (Pcs) and their precursors, subphthalocyanines (SPcs) are pyrrolic macrocycles, most commonly used for their optical properties in applications such as photovoltaics, light emitting diodes, and fiber optic telecommunication. Recent studies have shown that Pcs and SPcs also have potential as cell imaging dyes. SPcs are converted into Pcs through a Kobayashi ring expansion reaction. This has led to a shift in focus toward the development of SPcs as reaction intermediates in a route to create highly unsymmetric Pcs. Herein, we report low symmetry SPcs as cell imaging probes, made by cyclizing 2,3-naphthalenedicarbonitrile and tetrafluorophthalonitrile in the presence of boron trichloride. In addition to potential as standalone fluorescent imaging probes, these SPcs can be used as intermediates for low-symmetry Pcs. Strong electron withdrawing groups impart stability for Kobayashi insertion reactions and insertions with a number of isoindolines and dicyanides will be presented.<br/>

Low-symmetry subphthalocyanines as fluorescent probes and precursors for low symmetry phthalocyanines

253rd National Meeting (2017)

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