title: A Parallel-Displaced Directly Linked 21-Carba-23-Thiaporphyrin Dimer Incorporating a Dihydrofulvalene Motif.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383, Wrocław, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Berlicka
authors.affiliation: Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383, Wrocław, Poland.
authors.forename: Michał J
authors.initials: MJ
authors.lastname: Białek
authors.affiliation: Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie St., 50-383, Wrocław, Poland. lechoslaw.latos-grazynski@chem.uni.wroc.pl.
authors.forename: Lechosław
authors.initials: L
authors.lastname: Latos-Grażyński
keywords: NMR spectroscopy; carbaporphyrinoids; cleavage reactions; dimerization; dimers