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Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetrakis(pentafluorophenyl)porphyrin: a study using 1,3-dipolar cycloadditions under mild conditions
Authors:Juliana M de Souza  Francisco F de Assis  Carla MB Carvalho  José AS Cavaleiro  Timothy J Brocksom  Kleber T de Oliveira
Institution:1. Departamento de Química, Universidade Federal de São Carlos—UFSCar, Rodovia Washington Luiz, km 235, SP 310, 13.565-905 São Carlos, SP, Brazil;2. Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal
Abstract: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 °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 (∼30 mg mL−1) using 1H NMR experiments.
Keywords:Chlorin  Isobacteriochlorin  1  3-Dipolar cycloaddition  Non-aggregation  Photosensitizer
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