Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetralcis(pentafluorophenyl)porphyrin: a study using 1,3-dipolar cycloadditions under mild conditions

The 1,3-dipolar cycloaddition of meso-tetrakis(pentafluorophenyl)porphyrin and its nickel complex, with the bulky azomethine ylide dipole was studied under mild conditions, and yielded chlorin and isobacteriochlorin derivatives self-prevented from aggregation. The reactions were performed at room temperature or 0 degrees C, and we were able to establish a set of reaction conditions to obtain only the chlorin or the isobacteriochlorin. These compounds were evaluated in solution, and no aggregation was observed at less than 25 mM (similar to 30 mg mL(-1)) using H-1 NMR experiments. (C) 2014 Elsevier Ltd. All rights reserved.