Synthesis of non-aggregating chlorins and isobacteriochlorins from meso-tetrakis(pentafluorophenyl)porphyrin: a study using 1,3-dipolar cycloadditions under mild conditions |
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| Authors: | Juliana M. de Souza,Francisco F. de Assis,Carla M.B. Carvalho,José A.S. Cavaleiro,Timothy J. Brocksom,Kleber T. de Oliveira |
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| Affiliation: | 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 |
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| 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. |
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| Keywords: | Chlorin Isobacteriochlorin 1,3-Dipolar cycloaddition Non-aggregation Photosensitizer |
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