A Parallel-Displaced Directly Linked 21-Carba-23-Thiaporphyrin Dimer Incorporating a Dihydrofulvalene Motif
Dr. Anna Berlicka
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland
Search for more papers by this authorMichał J. Białek
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland
Search for more papers by this authorCorresponding Author
Prof. Dr. Lechosław Latos-Grażyński
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland
Search for more papers by this authorDr. Anna Berlicka
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland
Search for more papers by this authorMichał J. Białek
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland
Search for more papers by this authorCorresponding Author
Prof. Dr. Lechosław Latos-Grażyński
Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383 Wrocław, Poland
Search for more papers by this authorAbstract
In the search of porphyrin arrays with a unique geometry, the efficient synthesis of a directly linked 21-carba-23-thiaporphyrin dimer with the distinctive dihydrofulvalene bridging motif has been developed. This compound acquires an uncommon parallel-displaced arrangement of two carbaporphyrin planes. The dimer undergoes an acid-triggered cleavage to create of the asymmetric carbathiaporphyrin–carbathiachlorin dyad or 2,3-dihalo-21-carba-23-thiachlorin depending on choice of acid. A formation of a reactive carbocation intermediate is postulated to account for mechanism of cleavage.
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